“THE PERFECT MURDER OF BOBBY FRANKS: The Leopold and Loeb Case” #WeirdDarkness

“THE PERFECT MURDER OF BOBBY FRANKS: The Leopold and Loeb Case” #WeirdDarkness

Listen to ““THE PERFECT MURDER OF BOBBY FRANKS: The Leopold and Loeb Case” #WeirdDarkness” on Spreaker.

IN THIS EPISODE: Nathan Leopold and Richard Loeb should never have been friends, they were too different from on another. But they did have one thing in common – they both agreed to create the perfect murder – and a mundane pair of eyeglasses would be their undoing.

”The Perfect Murder of Bobby Franks” by Troy Taylor – from the book “Suffer the Children: American Horrors, Homicides and Hauntings”: https://amzn.to/3lo6CvP (Available on Kindle, paperback, and as an audiobook narrated by Darren Marlar)
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Originally aired: November, 2021


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On May 21, 1924, 14-year-old Bobby Franks left an after-school baseball game to walk the three blocks home to his house in the Kenwood neighborhood of Chicago, and simply vanished. After dinner, his worried father Jacob began calling and then looking around the neighborhood, but no one had any idea where Bobby was. At about 10 p.m., while Jacob was still out, his wife Flora was called to the telephone. A man identifying himself as “Mr. Johnson” informed her that Bobby had been kidnapped. The caller hung up, and Flora fainted. The Frankses spent a sleepless night frantic with worry before receiving, at 9 a.m. on May 22, a special delivery letter informing them that their son was still alive but that they must deliver a $10,000 ransom that afternoon in order to keep him safe. Jacob Franks was at the bank withdrawing the money as instructed in old $20 and $50 bills when a tip came in from a morgue in Indiana, near the Illinois border, that a boy’s body had been found in a drainage ditch in a nearby swamp. It wasn’t clear how or when or why the boy had died, but a Chicago Daily News reporter who’d seen the corpse phoned another Daily News reporter who was already staking out the Franks house to say that he thought someone from the family should come down to take a look. When the next phone call came later that afternoon from “Mr. Johnson” with further instructions for delivering the ransom, Jacob Franks was too distraught to follow what Mr. Johnson was saying because another call had just come in from his brother-in-law down at the morgue: the body of the dead boy was, indeed, Bobby’s. The fact that a millionaire’s son had been found mysteriously murdered was instant front-page news in Chicago. And the story only gathered steam over the next few days, as the papers filled with speculation: Why had Bobby’s killer not even waited to get the ransom? Why did the ransom note have such an oddly literary quality? And who owned the pair of spectacles found lying on the ground near the body?

I’m Darren Marlar and this is Weird Darkness.


Welcome, Weirdos – I’m Darren Marlar and this is Weird Darkness. Here you’ll find stories of the paranormal, supernatural, legends, lore, the strange and bizarre, crime, conspiracy, mysterious, macabre, unsolved and unexplained.

Coming up in this episode…

Nathan Leopold and Richard Loeb should never have been friends, they were too different from on another. But they did have one thing in common – they both agreed to create the perfect murder – and a mundane pair of eyeglasses would be their undoing.

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Now.. bolt your doors, lock your windows, turn off your lights, and come with me into the Weird Darkness!



The killers arrived at the culvert just as the sun was going down. Nathan parked the automobile near the Pennsylvania Railroad tracks. As he climbed out from behind the wheel of the car, he glanced off in the distance and saw the way that the sun glinted off the twin rails as they vanished on the horizon. He pressed his lips together in a twisted grimace and opened the trunk of the car. He pulled out a pair of rubber hip boots and sat down on the back bumper to slide them on over his shoes. As he did so, the passenger door of the car creaked open and his partner, Richard, climbed out. The other young man stretched casually and let out a sigh. They had been riding around the Indiana countryside for hours, waiting for it to get dark. It felt good to get out of the car.

Wordlessly, Nathan opened the rear driver’s door and Richard walked around the back of the car to help him. Together, they reached for the bundle that had been shoved onto the floorboard behind the front seat.

As Nathan tugged on the bundle, wrapped in a gray blanket, he saw a crimson stain that was starting to seep through the heavy material. They needed to get this over with, get rid of it, and get on with the plan.

The bundle landed heavily on the muddy ground. Richard leaned down, grabbed one end of it, and unrolled it to reveal the still, bloody body of a young boy. Dressed in his school uniform, the thin, dark-haired boy was twisted in a tangle of limbs. His face was mottled and blackened, smeared with dried blood from the gaping wound in his head.

Nathan wondered for a moment if the boy might still be alive, but the corpse lay stiff and rigid on the ground. Its glassy eyes stared up at them, unblinking.

With no hesitation, Richard quickly began undoing the buttons on his jacket. Nathan started with his shoes, pulled off the boy’s socks, and they

stripped him naked. If the body was found, this would make him much harder to identify.

It was a warm night and Nathan was already sweating. His jacket felt tight and uncomfortable.

The dead boy, his arms by his sides and his legs slightly apart, now lay naked on the ground. Richard reached into his coat and pulled out a bottle of liquid. He handed it to Nathan. The other young man pulled out the glass stopper and held the bottle of hydrochloric acid above the corpse. He tipped it and some of the liquid fell on the dead boy’s face. The acid would burn away the skin. If someone discovered the body, the police would never be able to identify it. Nathan had been told by someone that it was possible to identify a person by the shape of their genitals, so he poured the remainder of the acid on the dead boy’s penis and testicles.

With this completed, they picked up the blanket like a stretcher and carried the corpse down a short slope toward the murky water that drained from the culvert and flowed into a swamp along Wolf Lake. Soon, they were standing knee-deep in the pool.

Nathan leaned down and picked up the boy’s body beneath the shoulders. He lifted him as high as he could and shoved the top of the corpse into the culvert pipe. He pushed as hard as he could, struggling to get the torso up over the lip of the pipe. It was a cool evening, but Nathan was drenched with sweat. He needed to get his coat off. He shrugged out of it, one shoulder at a time, and then handed it to Richard. As he did so, neither of them heard the quiet splash from the water at their feet. A pair of eyeglasses were in the pocket of Leopold’s coat and they fell into the water as he removed it.

This would be the undoing of their “perfect crime.” Richard took the coat and climbed up out of the water and mud as Nathan shoved the body into the pipe as far as he could. Satisfied that the corpse would not be seen, he sloshed out of the mud toward the car.

Both young men were convinced that the body would not be found until long after the ransom money had been paid. With darkness falling, though, Nathan failed to notice that one of the boy’s feet was dangling from the end of the culvert pipe.

The murder of Bobby Franks was about to become front page news.

On May 21, 1924, Jacob and Flora Franks were waiting anxiously for their son, Bobby, 14, to return home from school. It was past 6:00 p.m. and dinner was on the table. It was unlike the boy to be late. Bobby’s older brother, Jack, 16, could usually be counted on to watch out for Bobby, but Jack had been out of school all


week, in bed with the chicken pox. Josephine, 17, Bobby’s sister, tried to ease her mother’s fears. Bobby always played baseball after school. Perhaps he had lost track of time or had gone to a friend’s house for supper.

Jacob Franks agreed with his daughter. He admitted that it was unlike Bobby to be late for supper, but he couldn’t believe that anything bad could have happened to him. Their home was only three blocks from Harvard School, which Bobby attended, and the boy was old enough to know not to talk to strangers. Still, he was annoyed that his son could be so thoughtless and forgetful and was unhappy with him for causing his mother to worry.

Jacob and Flora were proud of their four children. Josephine had been accepted at Wellesley College in the fall. Jack, a junior at Harvard School was planning to attend Dartmouth College. Jacob, Jr. was the youngest child, still in elementary school, but showed signs of academic promise.

Bobby, the favorite of the entire family, was precocious and a bit of a troublemaker, but no one could stay angry with him for long. He was an independent boy, who got good grades, and already announced that he also planned to attend Dartmouth, where he planned to study law. The principal of Harvard School, Charles Pence, spoke glowingly of Bobby. Only a freshman, he was already a member of the debate team. He was a popular boy, a skilled tennis player, and an avid golfer. He had joined with some other boys at school and started a reading group. Only a few days before, he had won a debate on capital punishment, arguing for a link between criminality and mental illness. He protested the right of the state “to take a man, weak and mentally depraved, and coldly deprive him of his life.”

Jacob loved his children so much because he had lost his own father as a young boy. Family was everything to him. His mother had run a clothing store and then a pawnshop in Chicago, and in 1884, Jacob started his own pawnshop on Clark Street, just south of Madison. It was a good location and a good time to be in the business – gambling was then unregulated in the city and there were at least a dozen gaming houses within a block of Jacob’s pawnshop.

He soon built a loyal clientele. Gamblers soon found they could rely on Jacob to lend them as much as 90 percent of the value on their watches, diamonds, and rings and once their luck turned, they could easily redeem their property.

Jacob never ran for political office, but he was well-connected. Michael “Hinky Dink” Kenna, powerful and notorious Democratic alderman of the First Ward, spoke highly of Jacob as an honest businessman and so did many others. He became an integral player in the Democratic party and used his connections to make his fortune. An opportunity to buy stock in the Ogden Gas Company was a lucky break for Jacob and his business partner, Patrick Ryan, and they sold the stock to People’s Gas Light and Coke Company for an enormous profit – some said as much as $1 million. Jacob bought land in the downtown district and watched its value soar when the city moved the taverns, gambling parlors, and brothels farther south to the Levee. By 1924, Jacob was wealthy beyond his wildest dreams. He had a wonderful home in an upscale neighborhood, a beautiful family, and a contented life.

But all of that was about to change.

By 7:00 p.m., Jacob and Flora were beyond annoyed and were becoming worried. Bobby was still not home. Jacob telephoned his attorney and friend, Samuel Ettelson. Jacob had known the lawyer for many years and Ettelson was one of the most influential men in the city. He had served as the corporation counsel during the mayoral term of William Hale Thompson from 1915 to 1923 and was now a state senator for Cook County in the Illinois legislature. A respected Republican, Ettelson still had considerable influence with the police department and with the state’s attorney, Robert Crowe. If anything had happened to Bobby, Jacob could rely on his old friend to help launch a massive police investigation.

Ettelson arrived at the Franks house on Ellis Avenue by 9:00 p.m. The three adults spoke briefly in the living room and the attorney could see how upset Jacob and Flora were. He immediately got to work making telephone calls. He called teachers and staff members at the Harvard School but only Richard Williams, the athletic director, was able to offer much help. He said that Bobby had been the umpire at a pickup baseball game in a vacant lot at 57th Street and Ellis Avenue. Williams had seen Bobby leave the game to walk home around 5:15 p.m.

Ettelson suggested that perhaps Bobby had returned to the school for something on his way home. If he had, he could have been accidentally locked inside by the janitor. He and Jacob grabbed their coats and hats and hurried to the school. When they reached the building, they found it dark and quiet. The door was locked and there was no sign of the janitor. A window was open on the first floor so Ettelson boosted Jacob inside. He unlocked the door and the two men searched the building and then the school grounds. There was no sign of Bobby.

At home, Flora was waiting anxiously for her husband. It was now almost 10:30 and Jacob had been gone for nearly an hour. The children were asleep and the servants, except for one maid, had all retired to their quarters. The house seemed deathly quiet.

In the hallway, the clanging of the telephone caused Flora to jump in her chair. She heard the maid pick up the receiver and answer the caller. She brought the telephone into the living room and handed the receiver to Flora – had Bobby been found? She breathlessly answered and then heard a man’s voice in reply. She remembered it later as “more of a cultured voice than a gruff voice.”

The caller spoke quickly and clearly. Flora did not miss a word. “This is Mr. Johnson… your boy has been kidnapped. We have him and you need not worry. He is safe. But don’t try to trace this call… We must have money. We will let you know tomorrow what we want. We are kidnappers and we mean business. If you refuse what we want or try to report us to the police, we will kill the boy.”

The line went dead – the caller had hung up. Flora was motionless for a moment, still clutching the receiver, and then she fainted and fell onto the floor.

Just minutes later, Jacob and Ettelson returned. The maid was still holding Flora in her arms – she had tried to revive her with spirits of ammonia – and Flora regained consciousness just as her husband walked in the door.

At least they knew what had happened to their son – and that he was alive. Perhaps the kidnapper would call again that night, so Ettelson called the telephone company to put a trace on incoming calls. It was a risk – the kidnapper had specifically warned against it – but Ettelson was in a difficult position. He wanted to bring his friend’s son home, but he was also a public official and refused to give in to blackmailers. From his years as Chicago’s corporation counsel, Ettelson had vast experience with city affairs and with negotiating contracts with labor unions, utility companies, building contractors, and every kind of underworld boss that Chicago could send his way. However, nothing had prepared him for this. He was uncertain how to proceed. Should they inform the police? Or should they wait for another call? If they obeyed the kidnappers demands, were they still putting Bobby’s life at risk?

Ettelson paced the floor, trying to decide how best to advise Jacob and Flora. Of course, there was no way that he could know that the threat they faced was much less sophisticated than they could have imagined.

Or that the kidnapping had already become a murder. At 2:00 a.m., Ettelson finally decided that they should go to the police. Jacob was relieved. He could stand the inaction no longer – anything was better than waiting for the telephone to ring. Ettelson was not only connected in the police department, he was personal friends with Chief of Detectives Michael Hughes, and with Deputy Captain of Police William Shoemaker. Why not use his influence to get them to rescue Bobby?

The two men rushed to the central police station and explained the situation to the young lieutenant in charge, Robert Welling. He listened carefully but was reluctant to mobilize the entire department in the middle of the night. What if, in the morning, the whole thing turned out to be a juvenile prank? Ettelson agreed, perhaps fearing for his own reputation, if it didn’t turn out to be a kidnapping at all. Besides, hadn’t the kidnappers threatened to kill the boy if they contacted the police? “Perhaps,” he decided finally, “we better wait until morning before doing anything about it.”

Before Ettelson could return to the police station the next morning, a special delivery letter arrived at the Franks home. The envelope had six two-cent stamps on it and was postmarked in Chicago. It had been mailed either the previous evening or early that morning. The letter – written by “George Johnson”— promised that Bobby was alive, and it provided instructions for his return. It also warned again about the involvement of the police. The details of the typewritten letter were as follows:

Secure before noon today $10,000. The money must be composed entirely of old bills of the following denominations: $2,000 in $20 bills, $8,000 in $50 bills. The money must be old. Any attempt to include new or marked bills will render the entire venture futile. The money should be placed in a large cigar box and wrapped in white paper. The wrapping should be sealed with sealing wax.

Have the money prepared as directed above and remain home after one o’clock PM. See that the telephone is not in use. You will receive a future communication instructing you as to your future course.

As a final word of warning, this is a strictly commercial proposition, and we are prepared to put our threats into execution should we have reasonable ground to believe that you have committed an infraction of the above instructions. However, should you carefully follow out our instructions to the letter, we can assure you that your son will be safely returned to you within six hours of our receipt of the money.

The Franks were almost overwhelmingly relieved after the arrival of the letter. This was proof, they believed, that Bobby was alive. For a trivial sum, they would have their son back, safely home with them. Samuel Ettelson was also relieved – this was a professional kidnapping gang and the boy was now, as he’d feared, in the hands of some deviant.

His greatest fear had been alleviated – Bobby would be returned to them alive.

Around the same time that the letter arrived at the Franks house, a Polish immigrant named Tony Minke was walking along a path that ran parallel to the Pennsylvania Railroad tracks near Wolf Lake. Tony was a pump man for the American Maize Company and was coming off the night shift at the nearby factory. He was on his way to Hegewisch to pick up his watch from a repair shop before going home to sleep.

He usually enjoyed the walk along the wooded path – a scenic spot with a wide variety of trees, wild prairie rose, raspberry bushes, and scores of migratory water birds – but the morning of Thursday, May 22, would change his feelings about the area forever. As Tony passed a large ditch on his left, he looked down momentarily. Something caught his eye and he looked closer – was that a foot poking out of the drain pipe? He stopped and climbed down to take a closer look. He peered into the pipe and saw a child’s body, naked, and lying facedown in the muddy water.

In the distance, Tony could see four railroad workers on a handcar traveling slowly along the tracks in his direction. He climbed up the embankment and waved frantically at them to stop. As the men climbed down, Tony walked toward them, pointing back at the ditch. “Look, there is something in the pipe!” he cried. “There is a pair of feet sticking out!”

As the men pulled the body from the pipe and turned it over, Tony could see immediately that the boy had been murdered. There were three large wounds on his forehead and toward the back of his head, he could see large bruises and swelling. There were also marks on his back, running all the way from his shoulders to his buttocks. But perhaps the strangest thing was the appearance of the boy’s face – there were distinctive copper stains around the mouth and chin. The same stains were all over his genitals, too.

As the railroad workers carried the body to a second handcar on the tracks, Paul Korff, a signal repairman for the railroad, looked over the scene. He wondered if the boys clothing was lying nearby. If so, he should gather them up and bring them along. But Korff could see nothing – no shirt or trousers, not even shoes or socks. But he did see something. It was a pair of eyeglasses with

tortoiseshell frames. They were lying on the embankment. The men must have dragged them out of the water as they were pulling the corpse from the pipe. Perhaps they belonged to the boy? Korff put them in his pocket and joined the other men at the handcars.

Around 10:00 a.m., Sergeant Anton Shapino took charge of the body at the Hegewisch Police Station. Paul Korff handed him the tortoiseshell eyeglasses and Shapino, assuming they belonged to the boy, placed them on the child’s forehead.

Later that morning, at the morgue at 1330 South Houston Avenue, undertaker Stanley Olejniczak laid the body out. He also noticed the unusual discoloration on the boy’s face and genitals and the damage that had been done to his head.

Whoever this child was, he thought, someone had beaten him violently.

Meanwhile, at the Franks house on Ellis Avenue, the family was waiting anxiously for word from the kidnappers. Jacob had already obtained the $10,000 in old bills and was ready to deliver it to whatever location the kidnappers demanded. They expected the ransom instructions by 1:00 p.m. but the hour passed. Another hour passed. The telephone didn’t ring. Jacob sat in an armchair and stared out the window at the street outside. His wife sat by his side, silently weeping.

Samuel Ettelson stayed in the library answering calls and talking with visitors. Ettelson was annoyed that the press had learned of the kidnapping. He assumed that someone at the telephone company had alerted a reporter after he requested a trace on all the incoming calls to the house. Even as the Franks waited in the living room for a call, he was being badgered by James Mulroy, a reporter for the Chicago Daily News, about the body of a boy that had been found early that morning near the Indiana state line. Of course, this was not Bobby. Mulroy had said the boy was found wearing eyeglasses and Bobby had never worn eyeglasses in his life.

But Ettelson had to be sure. He contacted Edwin Gresham — the brother of Flora Franks and Bobby’s uncle – and asked him to go down to the morgue with the reporter and take a look at the body. And if, by some chance, it really was Bobby at the morgue, he should telephone the house and say only one word – “Yes” – over the line; nothing more. There was a telephone extension in the living room and Ettelson did not want Flora to overhear the news of her son’s death.

The telephone rang 30 minutes later. Ettelson picked up the receiver and he recognized Gresham’s voice. “Yes,” the man choked out. The line went dead and Ettelson placed the receiver back in its cradle with shaking hands. He walked into the living room. Flora had left the room, but Jacob was still sitting in the armchair, staring at the street outside. He looked exhausted.

Ettelson leaned over and whispered in his friend’s ear that Bobby was dead. Jacob looked up into Samuel’s eyes. “What do you mean?” he gasped. “That your boy is dead.” At that moment, the telephone rang. Ettelson picked up the receiver. “Hello, is Mr. Franks in?” asked the voice at the other end of the line. “Who wants him?” “Mr. Johnson wants him.” “Who is that?” “George Johnson.” “Just a minute,” Ettelson replied and as he passed the telephone to Jacob, he whispered that it was the kidnapper. Jacob was still in a daze. He was still stunned by the news that his beloved Bobby was dead. “Yes?” he mumbled into the receiver.

“This is George Johnson speaking. There will be a Yellow cab at your door in 10 minutes. Get into it and proceed immediately to the drug store at 1463 East 63rd Street.”

“Couldn’t I have a little more time?” “No sir, you can’t have any more time. You must go immediately.” Ettelson didn’t know what to do. Edwin Gresham said that Bobby was dead. Why was the kidnapper still looking for the ransom money? Could Bobby still be alive? The Yellow Cab soon arrived, waiting in the street with its engine running. Jacob was exhausted – he hadn’t slept in more than 36 hours — and couldn’t remember the address of the drug store, only that it was on 63rd Street. Ettelson pleaded with him to recall the location of the drugstore but it was no use. Jacob was confused, shocked, and sad – it was simply gone from his mind. He sat back down in the armchair. He wasn’t going to be delivering any ransom money today. Ettelson paid off the cab driver and stood on the sidewalk and watched it drive away. Had they missed their only chance to rescue Bobby? No, it was too late, he knew. Bobby was already dead.

Word of the kidnapping and murder quickly spread. The newspapers began putting “extra” editions on the street, alerting the public to the gruesome crime. Morgan Collins, the chief of the Chicago Police Department, promised that he would commit all his resources to tracking down the killers. Collins undoubtedly exaggerated when he described the killing as “one of the most brutal murders with which we have had to deal. Never before have we come in contact with such cold-blooded and willful taking of life,” but people were genuinely outraged. It shocked the entire city.

In the early morning hours of Friday, May 23, the police began rounding up the first suspects – teachers at Bobby’s school. Walter Wilson, math teacher; Mott Kirk Mitchell, English teacher; and Richard Williams, athletics coach, were dragged out of bed and taken to the Wabash Avenue Station. Over the next two days, the police also brought in chemistry teacher Fred Alwood; George Vaubel, the physical education instructor; Charles Pence, school principal; and Edna Plata, the French teacher.

The reasoning behind the rounding up of teachers was simple – they had access to the boy, they knew Jacob Franks was wealthy, and, most tellingly, because the ransom note had been so well-written and without mistakes. Only an educated person could have written it, detectives reasoned. Hugh Sutton, an expert with the Royal Typewriter Company, thought the kidnappers had used an Underwood Portable Typewriter, less than three years old, and the typist had used two fingers to compose the letter. “The person who wrote this letter,” he stated, “never learned the touch system. The touch system strikes the keys pretty evenly, with an even pressure on the keys. The man who wrote this was a novice at typing. Some of the letters were punched so hard they were almost driven through the paper, while others were struck lightly or uncertainly.” Jacob’s name had been printed by hand on the envelope in block letters. Handwriting experts determined the letters displayed a uniform slant and regular spacing character. It was obviously the penmanship of a capable writer.

In other words, the police surmised, it must be a teacher. It wasn’t, but it took detectives some time to figure that out. Some of the faculty were grilled harder than others. For instance, Walter Wilson was unmarried and had no girlfriend. He’d also shown an unusual interest in the Franks children. Several months earlier, he had taken Bobby and his younger brother, Jacob, Jr., on an excursion to Riverside Park and had not returned with the boys until almost 1:00 a.m. Could he be a ped–phile?

Both Richard Williams and Mott Kirk Mitchell were held in police cells for five hours that Friday. Officers beat both men with rubber hoses, trying to get them to confess. Detectives had searched Williams’s apartment and found four bottles of brown liquid. Could it be what had stained Bobby’s face and genitals? Williams protested his innocence. The liquid was nothing more than a liniment that he used on the boys’ muscles when they became sore after strenuous exercise. But it did him no good to explain – he remained a suspect.

It was learned that Mott Kirk Mitchell had a semiannual mortgage payment due on the day of the kidnapping and when it was discovered the amount of the payment was exactly $10,000, the police were sure they had their man. The police searched the sewers around Mitchell’s house for Bobby’s clothing but found nothing. Mitchell insisted that he was innocent.

Fortunately for the teachers, they all had solid alibis for the night of Bobby’s disappearance. Mitchell’s neighbors had seen him working in his garden at the time of the kidnapping. Richard Williams had had dinner at the Delphi Restaurant and Walter Williams’s landlady stated that he had been home all evening. Friends, acquaintances, and neighbors said that it was impossible that any of them could have killed Bobby – there were kind, considerate, and upstanding gentlemen.

But Robert Crowe, the Cook County State’s Attorney, was still suspicious. Even though there was no evidence linking any of the teachers to the crime, he refused to order their release. The police held the suspects for four days, beating them regularly, and yet had been unable to force a confession. Finally, the men’s lawyers had filed a petition for a writ of habeas corpus on Monday, May 26, alleging police brutality. There was no justification, they said, for their clients’ continued detention. Against the pleadings – and even sly suggestions – of Robert Crowe, Judge Frederic Robert DeYoung ordered their release.

Samuel Ettelson was furious about the teachers’ release, believing that the killer was among them. In a rare display of anger, he was quoted by Chicago newspapers as condemning the release – he asserted that at least two of the teachers had plotted to kidnap Bobby. “One instructor at the Harvard School killed Robert Franks,” he claimed. “Another wrote the polished letter demanding $10,000 from the family. The instructor who wrote the letter was a cultured man – a man with perverted tendencies – the man who committed the actual crime is a man who needed money and had mercenary motives.”

Ettelson’s anger was also being felt by police officials. One week after the murder, they had several clues, plenty of theories, dozens of leads, but no arrests. Then, they discovered they had a witness to the kidnapping – just after 5:00 p.m. on Wednesday afternoon, Irving Hartman, 10, a student at the Harvard School, had been walking behind Bobby on Ellis Avenue. Irving had looked away at some flowers in a yard and when he glanced back up, Bobby was gone. At that moment, Irving told detectives, a gray Winton automobile was pulling away from the curb where he had last seen Bobby.

Phillip van Devoorde, a driver for the Fay family, had also seen a gray Winton, spattered with mud, outside Harvard School on May 20, the day before the kidnapping. The driver provided a more detailed description of the car – it was a 1919 model with a gray-black top; the driver was 25-30-years old; a second man was in the passenger seat with a red face, pointed nose, and tan cap. He had also seen the same car standing near the front entrance to the school on Wednesday, around 5:00 p.m. – almost exactly at the time of the kidnapping.

When word got out, sightings of gray Wintons began pouring into police headquarters. One witness spotted a gray Winton near Wolf Lake on Wednesday evening around 8:00 p.m. A man had been behind the steering wheel and a woman had been in the passenger seat. In the back? They swore there was a large bundle that might have been a human form. A tax assessor named William Lucht said that he had seen a Winton with two bundles in the back seat near Cottage Grove Avenue and 67th Street on Wednesday evening. Stanley Milner had seen a gray Winton on Lake Park Avenue and 48th Street. Frederick Eckstein, a watchman, had noticed a gray touring car – “old and decrepit looking” – near Wolf Lake.

State’s Attorney Crowe took each sighting seriously. Irving Hartman had no reason to lie about what he’d seen. Besides, the Winton was not a popular model and it wouldn’t be difficult to track down every Winton owner in the city. It was a distinctive car with a boxy appearance and an elongated hood that made it instantly recognizable.

Anyone with a Winton found himself liable to be arrested on sight. Two days after learning of Irving’s account, the police picked up Adolph Papritz, a draftsman for Armour and Company, because he owned a gray Winton. He was eventually cleared, but not before the newspapers had concluded that he was probably the killer. Papritz was understanding, though. When he was released, he told reporters, “I expected it. Everybody with a gray car is being taken in.”

Joe Klon was unlucky enough to not only drive a gray Winton – he wore tortoiseshell glasses, too. After a dozen or so people turned him into the police, he started leaving his car in the garage and walking to work. Klon told newspapers, “This has got to stop somewhere. I’m going to have my car painted black. I’ve got to wear glasses to see, but I’m going to do away with these tortoiseshell rims. This is the third time that I’ve been arrested for murder in as many days.”

The strategy of advertising the clues in the case brought in hundreds of leads – all of which led nowhere. Detectives searched out gray Wintons in every part of the city, hauling in their owners for questioning, and interviewing countless mechanics at car repair shops. Not a single gray Winton could be linked to the murder.

Irving Hartman’s eyewitness account, Crowe eventually realized, had been mistaken.

The investigation shifted to try and understand the killer’s motive. Chief Collins was convinced that this might lead detectives to the murderer. But why had Bobby been killed? No one seemed to be able to agree on a reason.

Could it have been for revenge against his father for a business deal that went bad? Jacob Franks had a reputation as an honest businessman, but it was difficult to believe that in his long career as a pawnbroker that he might not have crossed some vengeful gambler, thief, or pimp. In fact, Bobby’s death had sparked a flood of hateful letters to the Franks household. One anonymous writer promised to “strangle you to death. You shall suffer minute by minute, you lowdown skunk.” The letter concluded with a threat to kill Jacob’s daughter, Josephine. The threats might have been the work of cranks, but they could not be taken lightly. Could his other children be at risk? No one was prepared to ignore the possibility that someone was planning a second kidnapping or attack against the family. Because of this, a police guard, made up of eight rotating officers, was set up around the Franks house.

Had Bobby been taken by a child molester? Publicly, coroner’s physician Joseph Springer claimed that “young Franks had not been the victim of a pervert.” However, in his final report, Springer hinted that someone may have raped the boy, based on damage to his rectum. Chicago had no shortage of pedophiles. Perhaps the abductor had molested Bobby and, fearing identification by the boy, decided to kill him.

But why the elaborate kidnapping hoax? Would a kidnapper interested in sexually abusing a young boy also telephone the boy’s parents, arrange for a cab to arrive at the Franks house, and mail a letter asking for ransom? That was possible, of course, but in the opinion of state’s attorney Robert Crowe, it was very unlikely.

Crowe believed the murder was a consequence of a ransom demand gone awry. The kidnappers had lured Bobby into an automobile – did he know his abductors? – perhaps with one of them hiding the boy in a remote location while the second kidnapper stayed in the city to telephone the parents and mail the letter. Bobby probably recognized the first captor, who had killed him not long after the kidnapping. The second man, unaware that their victim was dead, had proceeded with their plan.

Crowe suggested that cocaine addicts, in the employ of a criminal mastermind, had abducted Bobby Franks. It should be noted that there was absolutely no evidence to support this wild conjecture, but Crowe didn’t care. He knew that by linking illegal drugs to the murder, he could legitimately call on outside assistance in the investigation. If the detectives of the Chicago Police Department were not up to the task, perhaps federal agents from the Bureau of Investigation could find the culprits. As he told a reporter, “We shall, by the process of elimination, try to find some one user of drugs who was sufficiently well acquainted with the habits and movements of the Franks family to have contrived a kidnapping plot – dope will be found at the bottom of it all.”

It was ridiculous, but the police had nothing else to go on at that point. They didn’t realize yet that the entire case would be broken by one innocuous item — a pair of eyeglasses.

On Monday, May 26, the Franks family held a funeral service for Bobby at their home on Ellis Avenue. It would have been impossible for the service to have taken place at a public location because the crowds would have been too large. The entire thing would have become a circus. Every day since the kidnapping, hundreds of curiosity-seekers had milled around outside their house, gawking at the locked door and drawn curtains, hoping to catch a glimpse of a mourning family member.

On that morning, a select group of people – members of the family, 20 of Bobby’s classmates, and a few close friends – gathered around a white casket in the library for the service. Flowers crowded the room and surrounded the coffin. The Lord’s Prayer was offered, followed by a reading of the Twenty-Third Psalm, and other passages from the scriptures. Two hymns were sung and then the mourners moved silently and slowly toward the front door, where black limousines waited to take them to Rosehill Cemetery, on the city’s North Side. Eight boys carried the casket to the hearse, while other boys from the Harvard School followed somberly behind.

There was now a crowd of 300 people waiting in the street. The family slipped out of a side door with a police escort to escape the photographers. Chief Collins had sent a large contingent of police to maintain order and there were no disturbances. At Rosehill Cemetery, prayers were offered, and Bobby Franks was laid to rest in the family mausoleum.

But, as we will later see, he would now rest there in peace.

The police investigation had come to a halt. Detectives had been unable to connect Bobby to anyone with a gray Winton like the one seen by Irving Hartman. There was no evidence to link any of the teachers from Harvard School to the kidnapping. They had been unable to identify the person who had written the ransom note.

There was only one clue left, which no one had bothered to pursue – those tortoiseshell eyeglasses that Paul Korff had found at the murder scene. It took more than a week, but the police finally realized that the eyeglasses were a valuable clue – and likely the only way to track down the killer. The lenses in the tortoiseshell frames could have only been obtained by prescription; they had not been purchased over the counter. Somewhere, there was an optician who had ground the glasses and that optician had a copy of the prescription in his files.

And if he had the prescription, then he had the name of the person who wore them.

Unfortunately, though, the prescription was a common one. It was given to “persons suffering from simple astigmatism or astigmatic farsightedness.” The lenses were of a convex cylindrical type, which was also common. The prescription alone wasn’t going to get them anywhere – there were thousands of Chicagoans with such glasses – but the frames turned out to be unusual. Composed of Newport zylonite, an artificial composite, the frames had distinctive rivet hinges and square corners. No firm in Chicago – or anywhere in the Midwest – manufactured Newport zylonite frames. They originated in Brooklyn, and only one optician in Chicago sold such frames: Almer Coe and Company. The owner of the firm recognized the glasses immediately. “We identified them as of a type sold by us and not by any other Chicago dealer. The lenses had markings used by us, and as far as we know, not used by any other optician in Chicago. The lenses are not unusual; such prescriptions are often filled by us, possibly once a week. They are lenses for eye-strain or headache and would not materially improve vision. They might be used only for reading or for what is known as mild astigmatism. Their measurements are average in every way.”

This seemed to be disheartening news, until detectives found out just how few of the tortoiseshell frames had been sold in the city. On Thursday, May 29, clerks at Almer Coe began the task of checking to see how many customers had purchased those particular frames, with that particular prescription. The number was shockingly low — only three pair of glasses with such unusual frames had been sold. One pair belonged to an attorney, who was away in Europe, the other to a woman, and the third pair had been sold to a young man who lived in the Kenwood neighborhood on the South Side.

State’s attorney Robert Crowe finally felt they were gaining ground in the investigation.

That afternoon, police officers knocked on the door of Nathan Leopold, Jr., a 19-year-old law student at the University of Chicago. He was taken into custody, but it seemed to be nothing more than for routine questioning. The reporters following the Franks case were only mildly curious. Leopold’s father was one of the wealthiest Jewish businessmen in the city and the family was socially prominent with influential connections. Nathan himself was a brilliant student who had recently applied to transfer to the law school at Harvard University.

Nathan Leopold obviously had nothing to do with the murder of Bobby Franks, they thought and returned to chasing other leads.

That afternoon was not the first time that the police had spoken to Nathan in the wake of Bobby’s murder. A few days earlier, on Sunday afternoon, he had spent two hours answering routine questions about Wolf Lake and the surrounding area. He had often conducted ornithology classes near the Pennsylvania Railroad tracks and had frequently taken boys from the Harvard School to the lake, as well as boys and girls from University High School.

The police had no reason to suspect him of anything and it quickly became apparent that their questions truly were routine. But Nathan had no time for distractions. He had decided to apply to Harvard University law school and that week, he was taking his entrance exams. He needed to concentrate, so he was particularly annoyed when the police returned to his family home at 4754 Greenwood Avenue with more irritating questions.

A maid answered Detective Frank Johnson’s knock at the door and he waited with other officers for several minutes until Nathan came downstairs. As Johnson introduced himself, he noticed Nathan’s irritation. He demanded to see the police officers’ identification. Johnson bristled at the arrogance in the young man’s voice.

After showing Nathan his badge and reciting his credentials again, he told Nathan that he was wanted at the state’s attorney’s office to answer some more questions. As the boy turned to get his jacket, Detective Johnson asked a quick question in an off-handed way, “By the way, do you wear glasses?”

“Yes.” “Did you lose your glasses?” “No, they are around here someplace.” But Johnson didn’t ask him to produce them. He was in a hurry. Robert Crowe had ordered him to bring Nathan to the Hotel LaSalle – not the state’s attorney’s office – in the downtown business district. Crowe was being cautious. Even though detectives had discovered that Leopold was one of the only people on the optician’s list who owned eyeglasses like those found at the scene that hadn’t been checked out, he could not link him otherwise to the murder of Bobby Franks. He had little desire to pull the Leopold family into the investigation without a good reason. If Nathan suddenly appeared at the Criminal Courts Building, reporters were bound to speculate. So, Crowe decided to meet with him in secret and give him a chance to provide an explanation as to how his eyeglasses could have been found near a corpse.

The meeting was short. Nathan said that he did have a pair of glasses like the ones that had been found, but that his were in the pocket of his coat at home. He could prove it if detectives wanted to take him home. When he arrived there, he made a show of searching for the glasses, but he now knew that the state’s attorney had one piece of evidence linking him to the murder of Bobby Frank – a murder that he had helped commit.

From that point on, the questioning of Nathan Leopold was no longer casual. The police searched his bedroom and study. They turned up two items. Neither of them connected him to the murder, but both the gun – a Remington .32-caliber automatic – and a letter from Nathan to a second boy, Richard Loeb, were unusual and unexpected. Nathan had no permit for the handgun, which made it illegal, but it was the letter that was the real puzzle.

As Robert Crowe read it over, he could discern that the two boys had quarreled – Nathan accused Richard of treachery and threatened to kill him but then wrote that he wanted to continue their friendship. The letter was alternately pleading, aggressive, and submissive. Nathan was angry with Richard and yet

desperate that they remain friends. If Richard broke off their friendship, Nathan concluded, “extreme care must be used. The motif of falling out of cocksuckers would be sure to be popular, which is patently undesirable, and forms an unknown but unavoidable bond between us.” There was no clue in the letter to say why Richard and Nathan had argued, but it was evident that the boys were lovers who’d had a fight.

Crowe decided to bring Nathan in to the Criminal Courts Building and now he wanted to talk to Richard Loeb. It was unlikely that the second boy – also the son of a wealthy and prominent Chicago businessman – knew anything about the murder, but Crowe could use Richard to get information about Nathan. Crowe had experience with this kind of blackmail – one hint that he would reveal Richard’s homosexual secrets and the boy would be willing to talk.

Crowe began hammering questions at Nathan Leopold in the interrogation room. It went on for hours, but he could not discover anything that he could use to link the young man to the murder. He demanded to know how Nathan’s glasses had ended up near Bobby’s body. Nathan had a quick answer to that – he had been birdwatching at Wolf Lake on the Sunday before the murder and he must have lost them then. He must have been walking right near the drain pipe where the “real killer” had placed the body.

Nathan told his story in a breezy, confident manner, calmly smoking a cigarette as he spoke. But when Crowe insisted that he place the eyeglasses in the coat pocket that he claimed that he’d been carrying them in, and then bend over to see if they’d fall out, he became flustered. He repeated the motion – which he claimed had caused the glasses to become lost – but they stayed securely in place. But it didn’t matter – he had an alibi for that day: Richard Loeb. They had been together all day and had dinner at the Cocoanut Grove Restaurant around the time of the murder, did some drinking, and then went looking for girls to pick up. After finding a couple of young ladies, they drove down Garfield Avenue, almost to Western Avenue, and then went to Jackson Park. They parked for a while east of the Wooded Island, but when the girls “wouldn’t come across,” the boys asked them to leave. A little later, they drove home.

As Nathan was presenting this alibi to Crowe, Richard Loeb was in an office in the Criminal Courts Building, telling the same alibi to one of Crowe’s assistants. The alibis offered by the two young men corroborated each other exactly. Richard also told the tale of the two girls – he recalled their names as May and Edna – and, like Nathan, recounted how he and his friend made them walk home after the girls refused to have sex with them.

Yet the alibi only made Crowe more suspicious. Crowe had not yet told Nathan that one of his detectives had found the latter that indicated that both boys were homosexuals. Why would they spend an evening trying to have sex with two girls?

The state’s attorney spent the entire night and into the next morning questioning Nathan, but the boy had still shown no signs of guilt. Richard Loeb was now in an adjacent room. Crowe decided to keep them both in custody, but everyone needed some sleep. He placed Nathan in a cell in the central police station and took Richard to the 48th Street Station.

While the boys slept in their cells on Friday, May 30, the press began to realize that Robert Crowe might have caught the murderers. Reporters from every newspaper descended on the Kenwood neighborhood to try and speak to the parents of Nathan Leopold and Richard Loeb. Of course, both families dismissed the idea that either boy could be involved with murder – they were certain they’d soon be released. It was all a terrible mistake that would soon be corrected. Both families even pledged to assist the state’s attorney in any way that they could, even allowing the boys to be held without charges so that the matter could be completely cleared up.

Robert Crowe couldn’t believe his luck and things were looking better for the case all the time. More evidence appeared that further convinced him of the two boys’ guilt. Nathan’s handwriting matched the writing on the envelope that contained the ransom letter. Not to mention, his eyeglasses had been found next to the body. The boys had concocted an alibi that could not be confirmed and late on Friday afternoon, tests confirmed that type legal notes that belonged to Nathan matched the typed ransom letter.

He was holding both suspects without any interference from their families, but he knew that, sooner or later, one or both families were going to alert their lawyers to the situation. Knowing this, he had to get the boys to confess before their lawyers ordered their silence. Neither boy had yet asked for a lawyer and neither had refused to answer questions – they just weren’t the answers that Crowe wanted. How could he get a confession?

In the end, he had some help. Two young reporters from the Chicago Daily News – Alvin Goldstein and James Mulroy, both of whom had been on the story from the beginning – had gone to school with Richard and Nathan and knew them both. They were surprised to find them in police custody but decided to try and match the legal notes that Nathan had written to the typewritten ransom letter. They provided the information about the letter to Crowe and suggested looking for the portable Underwood that he’d used for both the letter and the legal notes. They searched his house but didn’t find it. However, one of the Leopold’s maids, Elizabeth Sattler, admitted that Nathan did have a portable Underwood and that it had been in the house just a few days before the murder of Bobby Franks.

All along, Nathan’s father had been telling the police that his son could not have abducted Bobby and driven him out to Wolf Lake because the family’s driver, Sven Englund, had spent the day of the kidnapping working on Nathan’s car, fixing his brakes. Englund, when questioned by one of Crowe’s assistants,admitted this was true, but he added that Nathan was not home at the time. He had been picked up by a second boy who was driving a green car. They had left together and had not returned that afternoon.

Englund’s account had smashed the boy’s alibi. Crowe had been interrogating Nathan when the news was brought to him. He stopped talking. He now knew that both boys had been lying to him about their movements on the day of the murder. They both claimed they had been driving around in Nathan’s car all day and now Crowe knew the car hadn’t moved from the garage. Crowe had no time to lose. The Leopold family had sent Englund to the Criminal Courts Building with the belief that his story would clear their son. Perhaps even now, Nathan’s father was contacting a lawyer to get his son released. If Crowe could get the confession he so desperately needed, he’d have an open and shut case.

With all the new information in hand, he started over with his interrogations. He would play the two of them against each other and get them to talk. But Crowe was exhausted. He wasn’t sure how much longer he could continue the questions.

As it happened, Richard Loeb broke first. One of Crowe’s assistants, John Sbarbaro, had remained with Richard while Crowe was in his office gathering materials – and his wits. Nearly a half hour passed and then Crowe heard a sudden bustle in the hallways outside. Sbarbaro had left the room and was hurrying – almost running – toward Crowe’s office. The assistant state’s attorney was almost out of breath when he opened the door. Loeb wanted to talk to the state’s attorney, there was no time to lose.

“Quick, quick,” he said, “before the boy changes his mind!” Richard told Crowe everything. He said that the murder was a lark, an experiment in crime to see if the “perfect murder” could be carried out. He then denied being the killer and claimed that he had driven the car while Leopold had beaten and slashed Bobby Franks to death.

When his turn came, Nathan refuted this. It was Richard who killed Bobby. Finally, the boys were brought together and admitted the truth. Loeb had been the killer, Leopold had driven the car, but both had planned the crime together — they were both guilty of Bobby Franks’ murder.

The people of Chicago, and the rest of the nation, were stunned. It was fully expected that the two would receive a death sentence for the callous and cold- blooded crime.

It was a “perfect crime” that was not so perfect after all.

Nathan Leopold, or “Babe” as his friends knew him, was born in 1906. His grandfather, Samuel, had emigrated from Germany to the United States in 1846, settling in northern Michigan. He opened several small retail stores, each one close to the copper mines of the region, and business was good. A few years later, he opened more stores and soon his reach extended across the entire Upper Peninsula. But obtaining supplies to sell to miners and laborers had become a struggle – there was no railroad or adequate shipping lines to connect to Chicago, the closest big city.

Samuel bought his first steamship in 1867 and soon added two more to his small fleet. He moved to Chicago with his wife, Babette, and their six children, invested wisely, and gradually built up his shipping business so that when he died from septicemia in 1898, his Lake Michigan and Lake Superior Transportation Company was the largest shipping line on the Great Lakes.

His oldest son, Nathan, was born in 1860 and proved to be the kind of capable businessman that his father was. He inherited the family business, married his childhood sweetheart, Florence Foreman, bought a large home at 3223 Michigan Avenue, and made a second fortune manufacturing aluminum cans and cardboard boxes. Through his marriage – his father-in-law was financier Gerhart Foreman – he became connected to some of Chicago’s wealthiest and most prominent bankers. Within a single generation, the Leopolds had become one of the most successful families in Chicago.

In 1915, Nathan and Florence moved their family – three sons: Michael, Samuel, and Nathan, Jr. – from Michigan Avenue to Kenwood, eight miles south of the Loop. Their new home on Greenwood Avenue was a three-story mansion, stepped back from the street, and was considered one of the most unique homes in the area. It had an enormous rectangular living room, built in a modernist style, facing the garden on three sides. Around that, the architect had built a house in a traditional nineteenth century style, complete with gabled roofs.

The youngest son, Nathan, Jr., was happy to move to Kenwood – or at least as happy as he could manage to be. The boy — with his sallow complexion, gray eyes, thick black hair, and curiously asymmetrical face that gave him a scheming appearance – had always been a lonely and sorrowful child. For two years, he’d attended the local public school, just a few blocks from the family’s Michigan Avenue home. It had been a terrible experience. He often came to the attention of bullies and his classmates taunted and teased him relentlessly. He knew he was different. He was shy and studious and had little interest in sports. His parents were wealthy and each afternoon, at the end of the school day, his governess embarrassed him by appearing at the school gate to walk him home. And when his classmates discovered that Nathan had briefly attended an all-girls school at age six, the humiliation was complete.

Nathan felt that he had no one to turn to for help. His father was distant and aloof. His mother was bedridden after contracting some mysterious illness during her pregnancy with Nathan. His brothers were older by several years and they were not close. So, he turned to his governess, Mathilda Wantz, who had been hired in 1911. She was an attractive, strong-willed German woman with a heavy accent and a flirtatious manner. She quickly became a strong presence in the house and a substitute mother for the boys, especially Nathan. Florence loved her children – with special regard for Nathan, a weak, frail boy – but her illness forced her to give up control of the household to the governess.

It wasn’t long before the maids were gossiping about Mathilda’s scandalous behavior. It became common knowledge that she was having sex with Samuel, 17, and even with Nathan, who was only 12. Nathan was smitten with the governess and welcomed her affections. “I was thoroughly devoted to her,” he later said.

Regardless of what was happening at home, Nathan was excelling at his new school. After the family had moved to Kenwood, his father had enrolled him at the Harvard School, located at 47th Street and Ellis Avenue. The building was unremarkable-looking but the teachers were, without exception, conscientious and hardworking, devoted to the students, and determined that each boy should, if he desired, attend an excellent college.

Fewer than 200 boys attended Harvard School. The primary school included eight grades, with approximately 15 boys in each grade. The high school was made up of four classes, ranging from freshmen to seniors. The school emphasized academic excellence and the size of the classes enabled the teachers to give each boy individual attention. Occasionally, a boy might graduate and go directly into his father’s business, but more typically, every member of the graduating class went on to college. Most alumni went to the University of Chicago or to an elite private institution like Yale, Cornell, or Dartmouth.

The classes at Harvard School were too small to support sports teams and that was fine with Nathan – he was indifferent to that kind of activity. He loved the classwork. In addition to his assigned course, he took electives in German and classical Greek, and each year, he earned the standing of top in his class. He was still an outsider –his classmates regarded him as an eccentric loner – but by junior year, he had won a few friends who shared his interest in ornithology. He had a passion for collecting birds and kept his collection in a study that adjoined his bedroom. He had over 2,000 specimens. On weekends, he went to the Wolf Lake, southeast of the city near the Indiana state line, to hunt for new species for the collection.

By the spring of 1920, Nathan, 15, was a junior at Harvard School, but had come to the conclusion that he had no more to learn from his teachers. He had accumulated enough credits to skip his senior year and go straight to the University of Chicago. He was excited about the challenge and plans were made for him to enter the university’s freshmen class.

But that summer, in June 1920, Nathan made a new acquaintance, an impossibly good-looking young man with brown-blond hair, blue eyes, and a ready smile.

His name was Richard Loeb.

Like his new friend, Richard also came from a wealthy, well- connected family. His father, Albert, was the vice president of Sears and Roebuck and a close friend of millionaire philanthropist Julius Rosenwald. Richard’s mother, Anna, was an important member of the Chicago Women’s Club and an associate of Jane Addams, founder of the settlement house movement in the city. His uncle, Jacob, was a lawyer in private practice in 1920 but had once been president of the Chicago Board of Education. He had been responsible – most notoriously – for the “Loeb Rule,” which prevented teachers in public schools from going on strike.

Albert Loeb had begun his career as a lawyer. He had been admitted to the Illinois bar in 1889 and worked for the firm of Loeb and Adler for 12 years. In 1901, he had accepted Julius Rosenwald’s invitation to work for Sears and Roebuck and, within a decade, became vice president of the company. As the business expanded in the early part of the century, Albert accumulated a personal fortune of more than $10 million. He and Anna had four sons – Allan, who lived in Seattle and managed Sears and Roebuck on the west coast; Ernest, a student at Vanderbilt University; Thomas, who was in the eighth grade at the Harvard School; and Richard, who at 15 had just completed his freshmen year at the University of Chicago.

Richard had always been the smartest member of the family. At an early age, he had been encouraged by his governess, Emily Struthers, to read widely in history and literature. She introduced him to everything from the novels of Charles Dickens to the adventure stories of Ernest Thompson Seton. Historical novels, based loosely on actual events, were all the rage in America in the early 1900s and Richard became caught up in the craze, listing books like Ben-Hur and Quo Vadis as his favorites. Emily was ambitious for her young charge, imagining that he might grow up to be an ambassador or diplomat. She encouraged the literary classics but also made sure he read serious historical works, as well.

Richard was a dutiful student and always read the books that Emily picked out for him. But he never divulged his true obsession, which was for crime and mystery stories. He had discovered a copy of Frank Packard’s thriller The Beloved Traitor among his brother’s books. Alone in his bedroom, he spent hours reading about a famous criminal who could get out of almost any complex or dangerous situation. He became enthralled by such adventures – the more intricate the story, the better. He read every kind of mystery story that he could find, from Sir Arthur Conan Doyle’s stories of Sherlock Holmes to books by Maurice Leblanc, Wyndham Martin, and more.

In October 1917, just three months past his twelfth birthday, Richard entered the freshmen class at University High School, which was adjacent to the University of Chicago. The school had been created by John Dewey as a way to overturn the traditional methods of teaching. There was no rote learning or memorization. It was a new idea that was meant to encourage innovation, initiative, and experimentation. Dewey believed that students should be educated in the way that best prepared them for daily life, so students at University High were expected to solve practical problems creatively and in cooperation with their classmates.

Thanks to this, the first two decades of University High were filled with creative activity both inside and outside the classroom. The University of Chicago took special pride in the high school and offered resources and financial support to make it successful. In 1917, there were 500 boys and girls enrolled at University High. Many of them were sons and daughters of university professors. Extracurricular activities flourished at the school. There was a jazz band, symphony orchestra, Glee Club, Sketch Club, Discussion Club, and Engineering Club. Each class organized a Literary Society that met for readings, debates, and music recitals. There were three academic honor societies: Kanyaratna (for girls), Triplee (for boys), and Phi Beta Sigma, which was for any pupils with outstanding academic records. Boys from all four classes joined the Boy’s Club and the girls organized the Girl’s Club as a counterpart. The students organized three publications: The Midway, a literary magazine that was published every two weeks; The Correlator, the school’s yearbook; and University High School Daily, a four- page newspaper that appeared every day but Monday during the school term. There were also sports teams – football, soccer, and baseball for the boys and basketball for both boys and girls.

Richard was excited about his entrance to the school. His older brother, Ernest, was a senior and captain of the soccer team and would provide guidance if Richard needed it. But he didn’t believe he did. He was outgoing, easy to get along with, and made friends easily. He had no particular talents that set him apart from his classmates – he was not inclined toward sports and played no musical instruments – but he was likable and engaging and soon became popular. He joined the Discussion Club and the Engineering Club, two groups that recruited members from all four classes. Predictably, the upperclassmen dominated the affairs of both groups and Richard attended the meetings sporadically during his freshmen year and said very little. His reserved his enthusiasm for the meetings of the Freshmen Literary Society and threw himself into it wholeheartedly. There was rarely a meeting that went by without his contributions. He was an excitable presence, always volunteering his thoughts and remarks, and, perhaps for this reason, it was such a cruel disappointment when he narrowly lost the election for Freshmen Literary Club president to Henry Abt.

His election loss was the sole blemish on an otherwise successful year. Everyone liked Richard – he was one of the most popular boys in the class. Teachers liked him because he did so well in his studies and participated in class. In January 1918, at the start of the winter term, he was elected as treasurer of the freshmen class and in February, he helped organize the freshmen-sophomore dance. Like everything else he was involved in, it was a huge success.

Richard was doing very well at his new school, but his governess, Emily Struthers, had greater things in mind for him. Emily was an attractive woman in her early thirties with a strong sense of duty. She had moved to Chicago from her native Canada in 1910 and felt fortunate to have found a generous and considerate employer like Albert Loeb. She was determined to repay his trust in her by raising Richard in the best way that she knew. She was neither harsh nor cruel, but she expected to be obeyed.

Richard grew up knowing that he never questioned Emily’s commands. While his friends were off playing or fishing in the Jackson Park lagoon, he was reading and studying. Every evening, she sat beside him at his desk while he completed his homework to her satisfaction. Richard’s parents were too busy to interfere and trusted Emily to take care of things as she saw fit. She was a kind but domineering presence in the boy’s life – one that he grew to resent. As he got older, Emily’s close supervision became unbearable and he chafed at the situation. He began lying to Emily in order to avoid her watchfulness.

Richard entered the sophomore class at University High in September 1918. He was only 13-years-old, but Emily had already decided that he should graduate from high school the following summer, two years ahead of his class. It seemed, to Richard’s teachers, a nonsensical decision. It served no purpose and, in fact, might be harmful to the boy to carry such an accelerated workload. Richard was smart, they knew, but he was not as exceptional as his guardian believed him to be.

But Emily would not be dissuaded. She always felt that her lack of education was a disadvantage and she resented her inferior status as a governess. She blamed that on her failure to continue her education after high school. She believed that Richard would be a great lawyer or a professor and that would only happen with great effort. So, during his sophomore year, Richard took all the classes that would enable him to graduate in 1919.

During the fall term, Richard attended meetings of the Sophomore Literary Society, occasionally taking part in the activities and debates, but he soon ran out of steam. He was taking too many courses – and had too much work to do – to have time to participate in extracurricular activities. Emily’s demands were insistent. It became a struggle to complete his homework each week.

Emily pushed him all throughout this sophomore year. She sat with him every evening while he did his homework, discussed his progress with his teachers, and made sure that all his assignments were completed. Her persistence paid off. Richard graduated from University High in June 1919 – just a few days after his 14th birthday. He had earned all the necessary credits to enroll at the University of Chicago in the fall.

Emily was exuberant, but Richard simply felt drained. His success had come at a heavy price. He resented Emily’s insistence that he take so many courses. He was bitter that his parents paid no attention to his complaints. Most of all, he envied his classmates their freedom. He had missed out on everything that had made his freshmen year at University High so enjoyable.

It quickly became apparent that Richard – high school diploma or not – was ill prepared for college. He was 14-years-old when he first attended classes at the university. Most of his classmates were three, four, even five years older than he was. Richard struggled to keep pace with the demands of the college curriculum. He worked hard during his first year – Emily continued to supervise his work – but Richard was a mediocre student and his grades were disappointing. Even in history, his favorite subject, he performed dismally.

It became an inauspicious start to his college career. And Emily, who had played such an important part in Richard’s life, left the Loeb household in the summer of 1920 after his parents decided that Richard, now 15, no longer needed a governess. Emily had made some poor decisions, but she had been a constant source of emotional support in Richard’s life. Without her steadying presence, Richard, by his own admission, went off the rails. As he later said, “When she left, I sort of broke loose.”

It was the same summer that Emily left that Richard became friends with Nathan Leopold, an awkward, self-conscious, shy boy with no self-confidence who had attended Harvard School. Nathan would also begin at the university that fall. Richard had the advantage of already having spent a year at the University of Chicago and the two young men bonded over Richard’s explanation of what his new friend could expect in the coming semester.

They became close, despite the vast differences between them. Richard was outgoing and sociable while Nathan was backward and aloof. Richard impressed people with his easy charm, his sense of humor, and pleasant manner. Nathan, who had an air of disdain and arrogance about him, seemed to be exactly the opposite. Almost immediately, those who met him didn’t like him.

They seemed, to all appearances, to have nothing in common. Richard, without Emily, now had no reason to devote all his time to his studies. He had hoped to join a fraternity, but none of the Jewish fraternities on campus had taken his pledge because he was too young. Early in his sophomore year, he joined the Campus Club, a social organization for students who hadn’t yet pledged a fraternity. Members of the Campus Club copied the rituals and rites of fraternal groups and sponsored dances and events, but it was a poor imitation of the real thing. For Richard, as it turned out, the Campus Club was a bore. He preferred to spend his evenings drinking and gossiping with friends at one of the speakeasies on the South Side – the Granada Café on 65th Street was popular with college students – or picking up girls at the Trianon Ballroom, a dance hall at 62nd Street and Cottage Grove Avenue.

Richard’s friendship with Nathan was a puzzle. No one could understand why they were such close friends. They had no shared interests. Nathan never accompanied Richard when he went out drinking or joined him when he was out picking up girls. Nathan just seemed to want to graduate from the university as quickly as possible. He spent all his free time studying. He made such good grades that the university awarded him advanced standing. He was not the best or the most brilliant in his class, but he was hardworking and determined to make his mark.

It had never been easy for Nathan to make friends and he was delighted to have Richard’s companionship. There was so much to admire about him. He was friendly, good-looking, and had a sophistication and worldly knowledge that Nathan envied. As Nathan got to know him better during the winter quarter, he began to realize that Richard led a secret life. Perhaps if he had not been so anxious to obtain and keep Richard’s friendship, he might have noticed Richard’s purposeless, destructive behavior sooner, but he didn’t. By the spring of 1921, though, he had fallen in love with Richard. There was now nothing that he wouldn’t do for him. So, when Richard devised a plan to cheat at cards, he readily went along with the scheme. It was not for the money – both boys received generous allowances from their fathers – but for the sheer thrill of the experience. There was great pleasure in doing something wrong and, most importantly, getting away with it.

When Richard started suggesting other adventures, Nathan went along with them, even if he did not fully share his friend’s enthusiasm. Some evenings, Richard would have too much to drink and would insist that they find some deserted street close to campus, and while Nathan waited in the car, the engine running, Richard would smash the windshields of parked cars with a brick.

But those adventures only whetted Richard’s appetite for something more daring. He discovered that the ignition key of his mother’s car, a Milburn electric automobile, would fit any Milburn electric. Once he got his hands on a spare key, he started stealing Milburn electrics that were parked on the street. They had some close calls and narrow escapes. Once, an owner spotted Nathan and Richard sitting in his car and chased after them. On another occasion, the police questioned them about a stolen car, but they were never caught in the act.

Richard loved danger – the more dangerous the better – and he always sought to raise the stakes. It was difficult to explain – even to himself – why he felt he needed the rush, but he only knew that he did. Perhaps it was the knowledge that he was breaking the law that gave him a thrill, or perhaps his ability to evade detection, or even simple boredom, but over time, his need for danger escalated.

Richard’s fascination with crime stories and pulp mysteries fueled his imagination. In his mind, he was a master criminal who could not be caught. His narcissism was fulfilled because he had an admiring audience in front of whom he could perform – Nathan Leopold. He became a willing partner in whatever scheme his dominating friend came up with.

The planning that went into his misdeeds thrilled and excited him. During his sophomore year at the university, Richard – always accompanied by Nathan – carefully planned his acts of vandalism in advance. On several occasions, he set fires, none of which, however, resulted in a loss of life. He often left his house in the middle of the night to smash storefront windows in Hyde Park and Kenwood. The preparation for such incidents was almost as pleasurable as the acts themselves.

Nathan was a willing participant in whatever Richard wanted to do. He experienced neither excitement nor regret over the vandalism. In all honesty, he was indifferent to the mayhem they created. But his affection for Richard and his desire to be in Richard’s company were now so strong that there was nothing he wouldn’t do to hold onto his friendship. It meant everything to him. Richard needed him as an accomplice, and if that was what was needed to keep Richard in his life, Nathan willingly agreed to anything he asked for.

But their friendship almost came to an end. Richard was restless at the University of Chicago. During his freshmen and sophomore years, he had lived at home while studying at the university. Now he was about to become a junior and he was anxious to get away from his family. He had friends at the University of Michigan at Ann Arbor, about 300 miles from Chicago. He had visited there for some football games and it made the University of Chicago seem too quiet, too boring. In 1921, he announced to his parents that he intended to transfer to Michigan to finish his degree.

His parents were disinterested but Nathan was devastated. He was about to lose his closest – perhaps his only – friend. In his desperation, Nathan announced that he would also transfer to Michigan. So, in September 1921, they embarked on their next adventure together.

Everything went wrong for Nathan that fall. He came down with scarlet fever shortly before the start of the semester and arrived on campus after classes had already started. In October, his mother, Florence, died, succumbing to the illness that had kept her bedridden for years. Nathan went home to be with his family and remained until Yom Kippur so that he could attend a memorial service for his mother. When he returned to the university, he was stunned to find that Richard no longer cared to continue their friendship.

On October 17, Richard had become a pledge for the Zeta Beta Tau fraternity. Members of the fraternity had warned him that he was being seen too often in the company of Nathan Leopold, a suspected homosexual. This association was sure to ruin his chances for membership, so if he planned to join Zeta Beta Tau, he needed to cut Nathan out of his life.

Nathan was destroyed by the fact that Richard had abandoned him in favor of the fraternity. He led a solitary existence at school. He ate his meals alone and spent most of his time immersed in his studies. He earned good grades but there was little reason for him to remain in Ann Arbor. So, in the fall of 1922, he transferred back to the University of Chicago.

It was the best move that he could have made, and his life might have turned out much differently if he hadn’t later come back under Richard’s influence. During his final year in college, he began to seek out friends and to develop extracurricular interests. He joined the Il Circolo Italiano, a society devoted to the study of Italian culture, and became one of the group’s most enthusiastic members. He also joined the Undergraduate Classical Club, a literary society that organized meetings, dinners and stage productions. He achieved academic excellence, surpassing all expectations in his courses. He distinguished himself by proving worthy of election to Phi Beta Kappa, one of only 15 students from the university to receive the honor in 1923.

It was also during this time that Nathan developed an even greater love for ornithology. In his spare time and on weekends, he would drive to the marshland around Wolf Lake, near the Indiana state line, in pursuit of new bird species to add to his collection. Ornithology had always been a hobby and yet his studies had become so proficient that during his final year at the University of Chicago, he was able to prepare two scientific papers for publication in The Auk, the leading journal for professional ornithologists in the United States.

Nathan felt that he had redeemed himself. His stellar academic record during his final year at Chicago, his election to Phi Beta Kappa, his successful graduation – one year ahead of his class – fulfilled the promise that he had made to his mother before her death. He had promised to distinguish himself at the university – and he had. That spring, shortly before graduation, Nathan decided to become an attorney. He planned to enroll at the University of Chicago law school in the fall.

Richard Loeb also graduated in 1923. He left the University of Michigan after doing very little work but still achieving satisfactory work. When he received his degree, he was a few weeks away from his eighteenth birthday, making him the youngest graduate in the history of the school.

His university career had been lackluster. He had never joined any of the student societies or participated in any extracurricular activities. He never tried out for a sports team or volunteered his services for a student publication or joined the debate society or a discussion club. He had attended lectures when he had to but preferred to spend his time hanging around the fraternity house, playing cards, reading mystery novels, and chatting with his friends. He seemed – even to the fraternity brothers who liked him – to have lost the will to do anything with his life. He drank heavily, and he was drunk so often, even in the early afternoon, that it was sometimes difficult to tell when he was sober. His drinking became so bad – and he was so unfocused and eccentric – that he became an embarrassment to the fraternity. In his senior year, the executive committee of the fraternity formally censured him for his drunkenness and suspended his privileges as an upperclassman.

It was a pathetic conclusion to an inglorious college career. He received his degree but had no plans for the future. But Richard had always enjoyed history and so, in September 1923, he returned to the University of Chicago for graduate work, taking a course in American constitutional history during the fall quarter. Nathan was also at the University of Chicago that fall. He had received his degree earlier in the year but was taking four law courses that fall.

Tragically, it was inevitable that they met again and returned to their toxic relationship.

Within days, Nathan was once again enthralled with Richard. He fell in love a second time and found Richard willing to indulge Nathan’s desires. To his friends, Richard boasted of his sexual conquests – claiming to have many girlfriends among the coeds on the Chicago campus – but in truth, he had little interest in sex. This indifference led to his willingness to succumb to Nathan’s devotion.

Richard was not immune to Nathan’s attention and flattery. It was true that Nathan was annoyingly egotistical – he could spend hours bragging about his supposed accomplishments – and it quickly became tiresome to listen to his untrue boast that he could speak 15 languages. Nathan also, in Richard’s opinion, had a tedious obsession with the philosophy of Friederich Nietzsche and would talk endlessly about the mythical “superman” who stood outside the law, beyond any moral code that constrained the actions of ordinary men. Even murder, Nathan claimed, was acceptable for a superman if the deed gave him pleasure.

It was not that Richard had a moral objection to murder. In fact, he had a great contempt for conventional morality. But Nathan was pretentious, always yammering on about his intellectual superiority, sneering at the boring, ordinary people who obeyed laws that he chose to disregard. Were such speeches merely to impress Richard, who never had much use for the law when he was vandalizing cars and stores and setting buildings on fire? Or did he actually believe it?

It didn’t matter to Richard. He was glad to see Nathan finally coming around to his way of thinking. There was no pleasure in committing crimes alone. He needed a companion who could appreciate his careful planning and preparation – Nathan’s admiration made it all worthwhile.

Richard had been thinking – ever since his return to Chicago in the fall of 1923 – about how to commit the perfect crime. He had vaguely thought of kidnapping a young child, which would involve, of course, a ransom demand as an essential part of the plot. Richard knew that to obtain the ransom and still avoid capture would present a challenge like none he’d faced before.

He couldn’t wait to put his plan into action.

The plan took seven months to develop. The first step took place in November 1923, when they traveled to Ann Arbor, Michigan, to burglarize Richard’s former fraternity house. It was supposed to be a lark, with the added challenge that someone might recognize them from their days on campus. But they arrived on the night of one of the biggest football games of the year. The fraternity house was left unguarded and those who remained in the house were sound asleep, having drank too much during the celebration. They stole penknives, watches, several fountain pens, and about $50 from the pockets of garments hanging in the coatroom. It hardly seemed worth the six-hour drive from Chicago to Ann Arbor, but it had been more for the thrill of it than what kind of loot they’d be taking home.

As they made their way downstairs and walked across the living room toward the front door, Nathan noticed a typewriter on a writing desk on one side of the room. It was one of the latest models, a portable Underwood. He picked it up and took it with them.

It would be useful for typing up his notes from the law lectures.

It was on the long drive home from Ann Arbor that the final elements to the “perfect crime” finally came together. Richard’s need to escalate their crimes had become more pressing. They had carried out their robbery without a hitch, but he felt unsatisfied. They needed a more complex crime. It should be ambitious – a perfect crime – and one so intricate and complicated that planning and calculating its flawless execution would be a challenge. They would leave behind no clues for the police and no trace of their involvement. It would stand forever as a crime that was impossible to solve.

As Richard outlined his idea for the perfect crime, he grew more excited. They should kidnap a child, he proposed, and to make things more complicated, they would demand a ransom from the child’s parents. The money was not important, but it was needed to magnify the seriousness of the crime. They would have to leave directions in order to obtain the ransom, but no clues for the police. They would promise the safe return of the victim, but, of course, that would never happen. They would have to murder the child. It would be foolish to leave open the possibility that their victim might recognize them at a later date.

Would the victim be a boy or a girl? They argued back and forth, going over the benefits of either and then finally decided that they should kidnap a young boy, perhaps one of the students at the Harvard School, someone whose parents were wealthy enough to pay the ransom

It would be a brilliant crime, they mused, one that would shock Chicago with its daring. They would obtain the ransom, dispose of the body, and leave no clues behind. The police would never catch them.

No one would ever know who committed the city’s perfect crime.

Christmas and the New Year came and went. After the holidays, the boys picked up their studies again. Nathan resumed his law courses while Richard attended graduate seminars in the history department.

During this time, the details of the kidnapping plan gradually developed. They would lure the boy to their car; render him unconscious, perhaps with chloroform; and drive him to a deserted spot near the Indiana state line. Thanks to his birding expeditions, Nathan knew of a drainage culvert that ran beneath the Pennsylvania Railroad tracks, close to 118th Street and Wolf Lake. It would make the perfect hiding place for the body – no one would find it.

But how to kill the victim so that they could equally share in the death? It would be easy to put a bullet through the boy’s head, but in that case, Richard claimed, only the one who pulled the trigger would be the killer. Richard was adamant about the fact that they both had to participate in the murder. If both were guilty, then neither would have the advantage of confessing to the police. They should strangle the victim, each with a hand on one end of the rope.

Both of them needed to be jointly guilty of murder.

In the spring, the details of the plan became clearer. They rehearsed the method by which the ransom would be delivered on April 24. The plan was to telephone the victim’s father and send him to a drugstore at 63rd Street and Blackstone Avenue, adjacent to the local train station. He was to wait there for a call, board the train, walk to the rear carriage, and look in the telegraph box for a letter that would instruct him to throw the ransom – securely wrapped in a sealed cigar box – from the train five seconds after passing the distinctive red brick water tower of the Champion Manufacturing Company. They calculated that the package would fall close to 74th Street, where Richard and Nathan would be waiting to grab it and make a quick getaway.

The rehearsal worked perfectly. Nathan, waiting in his car at 74th Street, watched the train travel above him on the elevated tracks. The package landed as expected and Nathan snatched it up and drove away.

It was foolproof! What could possibly go wrong?

The next hurtle to clear was Nathan’s car. He drove a very memorable red Willys-Knight sports car, with nickel bumpers and disk wheels. It was much too distinctive to use for the kidnapping. If anyone saw it, they would certainly remember it and the police would have little trouble linking Nathan to the abduction.

They needed to rent a car, but they couldn’t do it under their own names. If the rental car was seen, the police would then be able to trace Nathan or Richard through the rental agency records. They would need a false identity to get a car they could use for the crime.

On Wednesday, May 7, Nathan walked into the Hyde Park State Bank and asked a teller about opening a checking account. He didn’t live locally, he said, and had no references in the area. He was a traveling salesman from Peoria. Would that be a problem? The teller thought it seemed like an odd request, but he said that it wouldn’t and passed him an information card that needed to be filled out. When completed, “Morton D. Ballard” made a $100 cash deposit into his new account.

On that same day, Richard entered the lobby of the Morrison Hotel at Clark and Madison Streets. He carried a suitcase in his hand – which contained four books for the weight – and checked in under the name of “Morton D. Ballard.” He was given the key to room 1031 and the bellboy took his bag upstairs to his room for him. An hour later, “Ballard” returned to the desk. He explained that he was a traveling salesman and would only be in Chicago one night but expected to return in a few weeks. There might be mail addressed to him at the hotel – would the desk be able to keep it for him until his return? The clerk was happy to arrange that for him.

Two days later, on May 9, Nathan walked into the office of the Rent-A-Car Company at 1426 Michigan Avenue. He had $400 cash in his pocket, right next to the passbook from the Hyde Park State Bank made out in the name of Morton Ballard.

He explained that he was new to the area – it was the first time that he had covered the Chicago area for his employer – and needed to rent a car. He had a bank account, but since he was a new customer, he was willing to put down a $400 deposit on the rental. He could also provide a reference – the telephone number of his friend, Louis Mason, who would vouch for him.

Two blocks away, Richard entered a lunchroom at 1352 Wabash Avenue, ordered some food, and told the counter clerk that he was expecting a call. The telephone rang a few minutes later – it was a call for Louis Mason. Richard gave a sterling reference for his friend, “Morton Ballard,” assuring the Rent-A-Car clerk that he was “absolutely dependable.”

The rental agency provided Nathan with the car for the day. He mentioned that he planned to return to Chicago in a couple of weeks and would need a car then. In that case, the clerk replied, the company would mail an identification card to his address – the Morrison Hotel.

They now had a plan for obtaining the ransom without risking capture and had created a false identity with which to obtain a rental car.

They were almost ready.

On Tuesday, May 20 – the day before the kidnapping – they purchased the equipment for the murder. Nathan bought writing paper and envelopes for the ransom note and then went to a drugstore at 4558 Cottage Grove Avenue. He asked the owner, Aaron Adler, for a bottle of hydrochloric acid and a half-pint of ether. The acid, he explained was for experimental work in a science laboratory at the university. He paid 75-cents for the bottle of acid.

Adler handed him the bottle. “Be sure to keep it upright,” he cautioned, “because it might leak out and burn your clothes.”

That afternoon, Richard completed their purchases, stopping at a hardware store on Cottage Grove Avenue, north of 43rd Street to buy rope and a sharp- edged chisel with a beveled blade and a wooden handle.

The next morning, they met at Nathan’s home and wrapped the handle of the chisel with adhesive tape so that it offered a better grip. They also found a blanket and tore some strips of cloth that could be used to wrap up and bind their victim. Nathan placed a pair of wading boots in the car because the boys planned to deposit the body in the swamps near Wolf Lake, located south of the city. He knew the area and feared that they’d need the boots in the swampy spots near the lake.

All they needed to do was to finish writing the ransom note. There was also one other thing that they’d overlooked – a victim. So far, they had not agreed on anyone but did feel that their victim should be small, so that he could be easily subdued. They had first considered killing Richard’s younger brother, Tommy, but they discarded that idea. It was not because Tommy was a family member but only because it would have been hard for Richard to collect the ransom money without arousing suspicion.

They also considering killing Armand Deutsch, grandson of millionaire philanthropist Julius Rosenwald, but also dismissed this idea because Rosenwald was the president of Sears & Roebuck and Richard’s father’s immediate boss. They also came close to agreeing to kill their friend, Richard Rubel, who regularly had lunch with them. Rubel was ruled out, not because he was a good friend to them, but because they knew his father was cheap and would never agree to pay the ransom.

They finally made a decision – Johnny Levinson, a 9-year-old boy in the same class at the Harvard School as Richard’s brother, Tommy. Johnny’s father, Sol Levinson, was one of the wealthiest attorneys in Chicago. He could certainly pay the ransom. Johnny was small enough that he would be easy to handle.

As they traveled to Kenwood, Nathan reminded Richard that directly across the street from the Harvard School, there was an alley that connected Ellis Avenue to a parallel road, Ingleside Avenue. They could park the car on Ingleside, walk along the alley to Ellis, and from the alley, watch the front entrance of the school until Johnny came out.

Nathan waited by the car while Richard walked through the alley to the school. He could see some of the boys were already by the main entrance. Some of the classes had ended already. He continued walking, past the entrance and along the north side of the school, toward the playground in the rear.

Suddenly, Richard saw Johnny, a thin, wiry boy with straight brown hair. He was less than 10 feet from where Richard was standing on the sidewalk. Could

he lure him away from his friends? And if so, how could he persuade him to leave the playground and walk with Richard to the car?

Richard started talking to him. The boy had a baseball in his hands. He was waiting on some friends, he explained to Richard, so they could walk over to the lot at 49th Street and Drexel for a pickup game.

Richard left the playground and made his way back over toward the main entrance. His little brother, Tommy, had finished his classes and was standing by the door, talking to another boy.

At that moment, Nathan appeared on the other side of Ellis Avenue, directly across from the main entrance. He whistled for Richard and then waved, urgently trying to draw his attention. There were some children playing on Ingleside Avenue, he told him. Why not take one of them? The street was otherwise deserted. There were no adults around.

No, Richard told him, he had a better plan. Johnny Levinson was on his way to a baseball game. They could go, watch the game, and then snatch him when he left to go home.

But it turned out to be too difficult to watch the game without being seen. They had to be careful. If someone spotted them, and then Johnny was kidnapped, a witness might link them to his disappearance.

While Nathan went home to get his binoculars, Richard stopped at the drugstore at 47th Street and Ellis Avenue. He would find the Levinsons’ address in the telephone book. Once they knew the street where Johnny lived, they would know the direction that he would take to get home.

But by the time they arrived back at the lot, Johnny had left the game. They waited to see if he’d return but after a half hour or so, they realized he wasn’t coming back.

They spent the rest of the afternoon driving around Kenwood, looking for a victim. Some children were playing near the Leopold house, but that opportunity also disappointed them – the children never left alone but always in small groups. By now, it was almost 4:30. They had spent two hours in Kenwood, waiting and watching, looking for a child to abduct. Nathan was ready to give up for the day. They could try again tomorrow. But Richard urged him to wait a little longer. They would drive around the neighborhood one more time.

Nathan drove west on 49th Street, turning left onto Drexel Boulevard. Richard sat in the back, behind the front passenger seat. At Hyde Park Boulevard, they turned left again, continuing east for another block. On Ellis Avenue, they turned north, passing the Loeb home. The street seemed deserted. It was almost 5:00 p.m. and the children had undoubtedly made it safely home.

And then they saw Bobby Franks. He was walking alone on the other side of the street. He was wearing a tan jacket with matching knee trousers, a colored shirt, and a necktie. Richard saw him first and he urgently tapped Nathan on the shoulder. But as Richard looked closer, he realized that he knew the boy. Bobby not only lived directly opposite from Richard on Ellis Avenue, he was also his cousin. Just the day before, he had played tennis with Bobby on the court at the rear of the Franks mansion.

Chosen by chance, he would make the perfect victim for the perfect crime. Nathan pulled the car up slowly alongside the boy. “Hey Bob!” Richard called from the rear window. Richard leaned forward, into the front passenger seat, to open the front door. “Hello, Bob I’ll give you a ride.” The boy shook his head – he was almost home. “No, I can walk,” he called back.

“Come on in the car. I want to talk to you about the tennis racket you had yesterday. I want to get one for my brother.”

Bobby was closer now, standing next to the car. He was so close that Richard could have grabbed him and pulled him inside, but he kept talking, hoping to persuade the boy to get into the front seat on his own.

Finally, Bobby slid into the front seat next to Nathan. “You know Leopold, don’t you?” Richard gestured toward Nathan. Bobby glanced at him but shook his head. “No,” he said. “You don’t mind us taking you around the block?” Nathan asked. “Certainly not,” the boy replied. Bobby turned around in the seat to face Richard and smiled at his cousin with an open, innocent grin. He was happy to see him and was ready to talk about yesterday’s tennis game.

The car continued along Ellis Avenue, going the opposite direction from Bobby’s house, and Richard reached down to the seat next to him and grabbed hold of the chisel.

At 50th Street, Nathan turned left. As the car made the turn, Bobby looked away from Richard and glanced toward the front of the car.

Richard reached over the seat. He grabbed the boy with his left hand, covering Bobby’s mouth so that he couldn’t cry out. He brought the sharp-edged chisel down savagely on the back of the boy’s skull. He raised his arm and struck again, pounding the chisel with all his strength. But Bobby wouldn’t stop fighting. He had now twisted halfway around in his seat, facing Richard, and desperately tried to raise his arms to protect himself from the blows. Richard smashed the chisel down two more times, slamming it into Bobby’s forehead, but he struggled for his life.

The fourth blow had opened a large gash in the boy’s forehead. Bobby collapsed onto the front seat. Blood from his head wound sprayed everywhere, it showered the seat, splashed onto Nathan’s trousers, and spilled onto the floor. Bobby held his hands to his head, curled up in pain on the seat, crying and wailing in pain. His legs were bent under his body, as blood continued to pour out of his head and onto the seat.

When Nathan saw the blood spurting from Bobby’s head, he cried out, “Oh God, I didn’t know it would be like this!”

Richard ignored him, intent on his horrific task. He reached down and pulled Bobby suddenly upward, up over the front seat into the back of the car. He jammed a rag down the boy’s throat, stuffing it as hard as he could, forcing it past Bobby’s teeth. He tore off a large strip of tape and slapped it over the boy’s mouth. Finally, Bobby’s moaning and crying had stopped! Richard relaxed his hold on Bobby and the boy slid off his lap and fell to the floor. A few minutes later, he wrapped him in a heavy blanket.

Bobby continued to bleed for a time and then died on the floorboard of the car.

Nathan kept driving. The car left the city in the direction of Gary, Indiana. A few minutes later, they were in open country. They followed side roads and dirt lanes, aimlessly circling. If they were going to dispose of the body safely, they had to wait until nightfall. There was nothing to do but remain in the car, which was stained with blood.

They both were hungry. They hadn’t eaten in hours. They drove the Indiana road, looking for someplace where they could get something to eat. Nathan stopped at the Dew Drop Inn, a roadside convenience store with large billboards on the outside walls offering Cracker Jacks and Coca-Cola. It was ready to close for the night, but Nathan returned to the car with hot dogs and bottles of root beer.

After they ate, Nathan started the car and headed back in the direction of Wolf Lake. By the time they arrived, it would be dark enough to dump Bobby’s corpse.

The sun had gone down by the time they reached the culvert near the Pennsylvania Railroad tracks. After pouring acid on Bobby’s face and testicles – which did not obliterate his identify as they believed it would and only left a rust-colored stain – they carried the body to the pipe and Nathan tried to shove it inside. He took his coat off to make the work easier. Unknown to the killers, a pair of eyeglasses were in the pocket of Leopold’s coat and they fell out into the water when he removed it.

After pushing the body as far into the pipe as he could, Leopold sloshed out of the mud toward the car, where Loeb waited for him. The killers believed that the body would not be found until long after the ransom money had been received. With darkness falling, though, Nathan failed to notice that Bobby’s foot was dangling from the end of the culvert.

They drove back to the city and parked the rental car next to a large apartment building. Bobby’s blood had soaked through the blanket and had stained the automobile’s upholstery. The blanket was hidden in a nearby yard and the boys burned Bobby’s clothing at Richard’s house. Nathan typed out the Franks’ address on the already-prepared ransom note. After this, they hurried back to the car and drove to Indiana, where they buried the shoes that Bobby had worn and everything that he had on him that was made from metal, including his belt buckle and class pin from the prep school.

Finally, their “perfect crime” carried out, they drove back to Nathan’s home and spent the rest of the evening drinking and playing cards. Later that night, they made the ransom call to the Franks’ house from a public telephone in the Walgreen’s drugstore at 47th Street and Woodlawn Avenue.

A woman’s voice came on the line and Nathan identified himself as “Mr. Johnson.” He told Flora Franks that her son had been kidnapped and that the family could expect a ransom note for his return.

It was finished. There was nothing left for them to do but to play out the rest of the game. They took the bloody blanket to an empty lot, burned it, and then drove to Jackson Park, where Richard tore the keys out of the stolen typewriter. He threw the keys into one lagoon in the park and the typewriter into another.

They placed the second call to the Franks family, instructing Jacob to take the ransom money and go to the drug store near the train tracks. But, of course, Jacob never went. By the time of the second call, Bobby’s body had already been discovered in the muddy pipe where they had left it. They were still waiting for the ransom money when the newspapers began putting together their “extra” editions and alerting the public to the tragedy.

The discovery of Bobby’s body began one of the largest manhunts in the city’s history. The “perfect crime” began to quickly unravel and Nathan and Richard were caught, thanks to a pair of eyeglasses that were dropped at the scene of the crime.

Confronted with evidence of their misdeeds, the two young men of “superior intellect” quickly confessed to the not-so-perfect crime.

In the wake of the confessions, the parents of the two killers turned to Clarence Darrow, America’s most famous defense attorney, in hopes that their sons might be saved. For $100,000, Darrow agreed to seek the best possible verdict that he could, which in this case was life in prison. “While the State is trying Loeb and Leopold,” Darrow said. “I will try capital punishment.”

Darrow would have less trouble with the case than he would with his clients, who constantly clowned around and hammed it up in the courtroom. The newspaper photographers frequently snapped photos of them smirking and laughing in court and the public, already turned against them, became even more hostile toward the “poor little rich boys.”

Darrow tried every trick in the book and resorted to shameless tactics during the trial. He declared the boys to be insane. Leopold, he said, was a dangerous schizophrenic. They weren’t criminals, he railed, they just couldn’t help themselves. After this weighty proclamation, Darrow actually began to weep. The trial became a landmark in criminal law. He offered a detailed description of what would happen to the boys as they were hanged, providing a graphic image of bodily functions and physical pain. Darrow even turned to the prosecutor and invited him to personally perform the execution.

Darrow’s horrifying description had a marked effect on the courtroom and especially on the defendants. Richard was observed to shudder and Nathan got so hysterical that he had to be taken out of the courtroom. Darrow then wept for the defendants, wept for Bobby Franks, and then wept for defendants and victims everywhere. He managed to get the best verdict possible out of the case. The defendants were given life in prison for Bobby Frank’s murder and an additional 99 years for his kidnapping.

Ironically, after all of that, Darrow only managed to get $40,000 of his fee from the fathers of the two young men. He got that after a seven-month wait and the threat of a lawsuit.

The verdict was a victory for the defense and a defeat for the state. Guards in the courtroom allowed Nathan and Richard to shake Darrow’s hands before escorting them back to their cells. Two dozen reporters crowded around the defense table to hear Darrow’s response to the verdict, but he was careful not to sound too pleased. “Well, it’s just what we asked for, but it’s pretty tough. It’s more of a punishment than death would have been.” As far as Darrow was concerned, he had defeated capital punishment, which was almost more important to him than saving the lives of the two young killers.

Nathan Leopold, Sr. had already left the courtroom – too overcome to talk to reporters – but Jacob Loeb remained behind to say a few words. “We have been spared the death penalty,” he said, “but what have these families to look forward to? Here are two families whose names here stood for everything that was good and reputable in the community. Now what have they to look forward to. Their unfortunate boys, aged 19 years, must spend the rest of their lives in prison. What is there in the future but grief and sorrow, darkness and despair?”

Robert Crowe was furious at the judge’s decision, believing that no two defendants deserved the death penalty as much as these two criminals had. It was a bitterly disappointing verdict, and in his statement to the press, Crowe made sure that everyone knew who was to blame: “When the state’s attorney arrested the defendants, he solved what was then a mystery. And by the thoroughness of the preparation of the case, the state’s attorney forced the defendants to plead guilty, presented a mountain of evidence to the court and made his arguments. The state’s attorney’s duty was fully performed. He is in no measure responsible for the decision of the court. The responsibility of that decision rests with the judge alone.”

The defense had spoken, as had the families of the defendants. The state’s attorney had made his excuses for the outcome of the trial, but in all of this, everyone seemed to have forgotten the victim. Had the state found justice for Bobby Franks?

His father spoke to reporters later that day. He was pleased that it was over and happy that there would be no appeal of the verdict. Jacob told reporters, “There can be no hearing in regard to their sanity. There can be no appeal. There can be no more torture by seeing this thing spread over the front pages of the newspapers. It will be easier for Mrs. Franks and for me to be relieved of the terrible strain of all this publicity.”

But was it truly over? No — and not for many years to come.

Neither Richard nor Nathan had ever expressed any remorse for the murder and neither thought to use their final interview with reporters to apologize to Bobby’s family – or to anyone else. Nathan, in his cell at the county jail, was his usual arrogant self. He called to Sheriff Peter Hoffman with one final request.

“Go out,” he ordered him, “and get us a big meal. Get us two steaks” – he held out his thumb and forefinger — “that thick.”

“Yes, and be sure they are smothered in onions,” Richard added. “And bring every side dish you can find. This may be our last good meal.”

Nathan still had one more thing, “And bring chocolate eclairs for dessert.” By 8:00 pm, Nathan was fast asleep on his bunk. Richard sat reading on the edge of his bunk, smoking a cigarette, occasionally looking up at the guards patrolling the corridor. Detectives had been stationed in the main lobby of the jail while uniformed police, in addition to the jailers, kept watch on the hallways and corridors. The two convicted killers were set to make a dangerous journey to Joliet Penitentiary the next day.

Feelings about the verdict in their case ran deep in Chicago. People were enraged that two pampered rich boys had gotten away with murder. It seemed every Chicagoan had wanted to see Leopold and Loeb swinging at the end of a rope. It seemed a travesty that Bobby Franks was in his grave while his killers were very much alive, eating chocolate eclairs, and bantering with reporters. The police had been forced to step up security around the jail and to make elaborate preparations for their transportation to the penitentiary.

Fears of an attack proved to be unfounded, though. A three-car convoy – including a Packard limousine, in which Nathan and Richard traveled – made the journey to Joliet. As they approached the high stone walls, they saw a huge crowd outside of the gates. As the cars approached, a roar of recognition went up from the mob. There was no time to waste getting Richard and Nathan into the prison. The gates clanged shut behind them and the locks turned to shut out the rest of the world. The prison, first opened in 1858, was a forbidding place. Richard stumbled on a paving stone as he stepped out of the car, but quickly caught himself. We’ll never know what he was thinking when he looked over the massive walls, metal gates, looming towers, and the prison guards that stared silently down at then with rifles in their arms, but it must have been intimidating. The warden, John L. Whitman, received their confinement papers from the Cook County sheriff, who turned to leave for the ride back to Chicago. It was 8:30p.m. and there was no time that night for the customary procedures – photographs, medical history, paperwork – so it all had to wait until morning. Three guards escorted the prisoners across the jail yard and to the isolation block for new prisoners. They had 10 minutes for a shower in the bathhouse and then they received a new set of clothes. Richard discarded his golf sweater and gray flannel trousers and Nathan removed his suit jacket and trousers and they changed into the standard prison uniform of a denim jacket and pants.

They were taken to their cells – Nathan at the east end of the block and Richard, as far away from his as possible, at the other end of the corridor. They were soon fast asleep, and they spent their first night in Joliet peacefully.

It was the first night of many to come.

Time passed, and Nathan and Richard grew accustomed to the daily monotony of prison routine. The guards placed Nathan in a cell in the East Wing of Joliet prison, and mindful that the two murderers be kept as far apart as possible, sent Richard to the other side of the penitentiary. He was locked in a cell in the West Wing.

The prison, after nearly 70 years, was a crumbling wreck. An unhealthy, unpleasant stench permeated the cell blocks, and each individual cell – dank, dark, and claustrophobic – was the worst space that one could imagine. There were no flush toilets and, in the morning, before breakfast, each prisoner carried his waste in a bucket to a large trough in the prison yard. The cells had been designed with windows so narrow that there was little natural light. It was unbearably hot in the summer and freezing in the winter months.

Nathan remained at Joliet prison only until May 1925, when he obtained a transfer to the new prison, Stateville, three miles north of the town of Joliet. The Stateville prion, built in anticipation of the closure of Joliet prison, consisted of four roundhouse buildings, each with an open tower in the center of a large space that was surrounded by a circular arrangement of cells. The guards in the central tower always had a good view of the prisoners in their cells.

Stateville was one of the most modern penitentiaries in the country but there was little discipline within the prison. The Illinois state legislature had provided funds to build the prison but had not provided a decent wage for the guards. As a consequence, corruption was rampant. A convict with money could buy any privilege that he desired, and by the early 1930s, the prison administration was no longer in control of the place. The inmates, as the adage went, truly were running the asylum. A dozen rival gangs competed for control of the prison. Each gang had constructed a motley collection of tar-paper shacks in the prison yard as its headquarters. Within the shacks, the gangs operated whiskey stills, grew marijuana plants, and hired younger and more vulnerable prisoners out as prostitutes.

In March 1931, Richard was also transferred to Stateville. Neither joined one of the many gangs operating behind prison walls, but, thanks to their wealth, they soon gained influence over other prisoners and curried favor with prison officials. They each enjoyed a private cell, books, a desk, a filing cabinet, and even pet birds.

Nathan also managed to ingratiate himself with the prison staff by using his education to the benefit of the clerical office. There were only six people in administrative positions for a prison that held almost 4,000 inmates. Successive wardens recognized his clerical talents as a valuable resource that helped the prison function more efficiently.

Frank Whipp, warden at Stateville in the 1930s, emphasized reform and rehabilitation in the management of the prison. A major purpose of the penitentiary, Whipp believed, was an end to recidivism – meaning that once a prisoner left, he stayed out of prison by not committing more crimes. The sooner that a prisoner demonstrated eligibility for parole, the better. Nathan quickly won his way into Whipp’s favor. There was little possibility that Whipp would recommend Nathan’s parole, but Nathan adopted the warden’s reform ideology and made sure that Whipp knew it. Nathan assisted the prison sociologist in his attempts to determine the suitability of various categories for early release and even published an article – under a pseudonym – on the subject in the Journal of Criminal Law and Criminology. Nathan received an appropriate award for these endeavors and, by his own account, soon had the run of the prison.

Richard was less eager to work alongside the prison administration. However, he also won a position of privilege, mostly because of the money at his disposal. Richard kept a permanent deposit of $500 in the prison office. This money, provided by his brothers, was available for his personal use at any time. His parents, unaware that Richard had a private banking arrangement with the prison, sent him an additional $50 each month.

Richard used his money wisely, carefully bribing the prison guards to grant him privileges. He had keys to parts of the prison normally accessible to prisoners at only certain times of the day and on a restricted basis. Richard was one of a small number of prisoners – Nathan was another – allowed to buy whatever he wished from the commissary. He was also allowed to eat in his cell or dine with Nathan in the guard’s lounge. It was not even necessary for Richard to wear a prison uniform – he customarily wore a white shirt and flannel trousers.

Richard also used his influence with the guards to pursue sexual favors from other inmates. Convicts who were willing to have sex with Richard might be rewarded with cigarettes, alcohol, a larger cell, or an easier job within the prison. Inmates who fell out of favor with him might find themselves shoveling coal in the yard or laboriously weaving rattan chairs in the furniture shop.

James Day was a 21-year-old serving a one- to ten-year sentence in Stateville for armed robbery when he first met Richard in 1935. Day was a small man – just five feet, six inches and 135 pounds – and had lived an unsettled life. He had never known his father and his mother had died in 1921. He moved to Chicago to live with his aunt and uncle and was constantly in trouble for fighting, theft, and petty crime. He was first arrested as a juvenile in 1928 and sent to the St. Charles School for Boys. He served a second juvenile sentence in the Boy’s Reformatory in Pontiac. In 1935, Day graduated to a cell in Stateville.

Richard took an immediate interest in Day’s welfare, perhaps seeing someone that he could easily manipulate, as he had done with Nathan. He arranged for guards to move Day to a cell in C House, in the same gallery as his own, and began sending the young man presents of cigarettes and small amounts of money. He also got Day a job in the prison office building and even hinted that he might be able to arrange a parole hearing for him.

It was a calculated scheme on Richard’s part to put Day into a dependent position so that he’d agree to have sex with him. Day resisted but Richard was persistent. He reminded Day that he might lose all his privileges if he didn’t submit. Wouldn’t it be easier, he asked, if he just went along with what Richard wanted?

On the morning of January 28, 1936, George Bliss, a convict in C House, secretly passed a straight razor to James Day. Just after noon, a work detail began its march from the dining hall, the prisoners in a double file line under the supervision of one guard. Day was the last in line, and his column passed through the prison, he slipped away when the guard wasn’t looking. Earlier that day, Richard had mentioned that he would be taking a shower at noon, casually suggesting that Day might meet him in the shower room. Richard had a key and could lock the door from the inside, allowing them to meet in private.

Day was in an angry, violent mood. Richard had been harassing him for weeks, demanding sex, and threatening to withdraw his privileges. When he entered the shower room, Richard advanced toward him, probably thinking that his persistence had finally paid off. Instead, Day struck at him with the straight razor, cutting him on the neck and abdomen, inflicting 56 wounds before he ran out of the room, leaving Richard on the floor in a pool of blood.

Of course, again, there’s no way to know what ran through his mind – shock, bewilderment, and terror, most likely – but it probably was not all that different than what went through Bobby’s mind on that day in the car.

Richard died later that day. The prison doctors worked furiously to save him, but Richard had lost too much blood. Nathan rushed to the prison hospital and watched helplessly as his friend lay dying on the operating table. When it was over, after the surgeons, doctors, and prison guards left the room, Nathan remained behind to wash the body and mourn the loss of the man who was once his closest companion.

James Day went on trial for murder later that year. He claimed self-defense and no one, not even Nathan, contradicted his story. The jury found him not guilty of murder.

Richard’s death caused an uproar outside the prison walls. When Clarence Darrow was told of his death, he slowly shook his head. “He is better off dead,” the great attorney said, “For him, death is an easier sentence.”

But most people were outraged to learn that Richard had corrupted the guards to gain special privileges. The new warden, Joseph Ragen, was deeply embarrassed and, as a consequence, Nathan found himself under sever scrutiny in case he, too, should step out of line. All of Nathan’s privileges were revoked.

The years that followed Richard’s death were lonely, bitter ones for Nathan, and yet, he survived and even began to contemplate the possibility of parole. To dream that he might get out of prison had once seemed impossible, but he knew that memories would eventually dim and perhaps he could convince the parole board that he was sorry for the terrible crime that he committed. At the time of Richard’s death, Nathan had already served 12 years and he would be eligible for parole in 1957. The parole board would require him to proclaim his regret for killing Bobby, but that would not be difficult. He would also need to show that he had been rehabilitated and if released, would never commit another act like the one that sent him to prison in 1924.

It is truly possible that Nathan was indeed sorry for the things that he’d done. Even though it had been his talk of superior intellects that were above the law that had inspired Richard to begin planning a “perfect murder,” Nathan, as arrogant as he was, would have never gone through with it on his own. Perhaps neither of them would have. But if we recall the year that Nathan spent separate from Richard – attending the University of Chicago, while Richard was in Michigan – we get a glimpse of the man that Nathan could have been without the horrible co-dependent relationship that he had with Richard Loeb.

Of course, this didn’t change the fact that Nathan had committed a heinous murder or that he had a long way to go to redeem himself. Nathan now immersed himself in the management of the school for prisoners that had been set up at Stateville. The school was an ambitious undertaking, offering classes in English, algebra, geometry, bookkeeping, and history. Money for pencils, paper, and other supplies came from the prison’s Inmate Amusement Fund. Nathan soon had over 400 prisoners taking classes, but its rapid expansion soon proved to be its downfall. The warden, Joseph Ragen, taking note of the popularity of the classes among the inmates, directed that each student’s academic record be reported to the central administration. Ragen intended that each of the prisoner’s accomplishments be presented to the parole board as tangible evidence of rehabilitation. But he had not seen the predictable outcome – prisoners with no previous interest in study, and with no desire to learn, began enrolling with the intention of forcing the teacher, by threats, if necessary, to award high marks to present to the school board in order to win early release.

In 1941, Nathan was transferred to a position as an x-ray technician in the prison hospital. Later that year, he wheedled his way into a position as a nurse in the hospital’s psychiatric ward. He now had more responsibility – and less supervision – than ever before. The prison doctors relied on the nurses to look after the psychiatric patients, even allowing them to medicate the patients in their care.

In September 1944, scientists working for the federal government came to Stateville looking for volunteers to test a new antimalarial drug. In Europe, World War II was in its final stages, but troops fighting in the Pacific still faced a challenge from the Japanese – and from a wide range of diseases, like malaria. Scientists had already started testing the drugs on patients at the nearby Manteno State Hospital for the Insane but needed more volunteers for the tests to be reliable.

Almost 500 prisoners – including Nathan – volunteered. He was dosed with malaria and on July 2, began showing symptoms. His body shook uncontrollably, his head felt as though it would split, and his fever shot up to 104. The symptoms lasted for five days and would reoccur two weeks later. The doctors administered the new medicine and while it turned out to be effective in preventing the appearance of symptoms, it was too toxic as a cure for malaria. Nathan, who had previously been healthy, now had signs of kidney disease and diabetes.

The “malaria cure” did permanent damage to his body but it also managed to get him some consideration for the length of his sentence. Thanks to his participation, Governor Adlai Stevenson, reduced his kidnapping sentence from 99 to 85 years. The difference might have seemed trivial because either way, he would spend the rest of his days at Stateville. But in terms of early release, he had

been eligible for parole in 1957 and now that had been moved up to as early as January 1953.

When Nathan did finally appear before the parole board, there was an air of sadness about him. The cockiness that he had shown at his trial was gone, worn down by the long years of incarceration. In its place was an air of quiet resignation. He’d gained weight, his hair was receding, and there was a sorrowful look in his heavy-lidded eyes. He said all the right things – his life had changed completely, his outlook had changed, he’d never get in trouble again if he was released.

Why did he murder Bobby Franks? How did he explain the killing? “I couldn’t give a motive that makes sense to me,” he replied. “It was the act of a child – a simpleton kid. A very bizarre act. I don’t know why I did it. I’m a different man now. I was a smart aleck kid. I am not anymore. I can only tell you that what happened in 1924 can’t happen again.”

He repeated that it had been a foolish act by two foolish boys and he was unable to account for the murder. “It seems absurd to me today, as it must to you and all other people. I am in no better position to give you a motive than I was then.”

Nathan had tried to make a good impression, but to his listeners across the table, his answers seemed trite and too quick, too rehearsed. There was still something about his manner that betrayed the arrogance of youth. His remarks, it was later reported, seemed almost offhand.

Simply put, he didn’t seem sorry for what he had done. His parole was denied.

Five more years passed before the parole board again met to consider Nathan’s release. The intervening years had given him time to prepare and to learn from his earlier failure. He hired an attorney, Elmer Gertz, to present his case to the board and he had reached out beyond the prison walls to enlist the support of prominent supporters. Former classmates had secured job offers for Nathan. All agreed that he needed to avoid a return to Chicago and the glare of the city’s newspapers. He had job offers from Florida, California, and Hawaii. The Church of the Brethren, which was based in Elgin, Illinois, offered him work in a mission hospital in Puerto Rico. A representative from the church had met Nathan’s brother, Sam, several years earlier and now offered to sponsor Nathan’s employment as a medical technician at the hospital.

The parole board met in February 5, 1958. Elmer Gertz presented a case for Nathan, highlighting his job offers, his work in the prison hospital, his exemplary record, and the length of time that Nathan had already spent in prison. Gertz blamed the length of his sentence on the publicity that surrounding the case, pointing to other inmates who had done worse things and who had already been released. He also urged the board to look back at the original court documents and see that it was Richard Loeb who had planned the scheme, initiated the kidnapping, and committed the murder. Yes, Nathan had been an accomplice, but the real blame, Gertz insisted, fell on Loeb.

A succession of character witnesses followed: John Bartlow Martin, a writer for the Saturday Evening Post who had interviewed Nathan in prison; Martin Sukov, a prison psychiatrist; Eligious Weir, the prison chaplain; and famous poet Carl Sandburg, who even went as far as to offer Nathan a room in his own home. All of them testified that Nathan had earned parole through his outstanding rehabilitation.

Finally, it was Nathan’s turn to speak. He had learned his lesson the last time around. He told the board, “It is not easy to live with a murder on your conscience. The fact that you did not do the actual killing does not help. My punishment has not been light. I have spent over one-third of a century in prison. During that time, I have lost most of those who were dear to me. I never had an opportunity to say a prayer on their graves. I forfeited all home and family. I forfeited all the chances of an honorable career. But the worst punishment comes from inside of me. It is the torment of my own conscience. I can say that will be true for the rest of my days. All I want in this life is a chance to prove to you and the people of Illinois, what I know in my heart to be true, that I can and will become a decent, self- respecting, law-abiding citizen, to have a chance to find redemption for myself by service to others. It is for that chance I humbly beg.”

The board members listened politely as Nathan spoke. When he finished, board president John Bookwalter asked Nathan about his attorney’s assertion that Richard had conceived and planned Bobby’s murder. Was it, he questioned, also Nathan’s belief that Loeb had a stronger personality and that he was more or less a follower?

Nathan agreed that this was true. “Through your adoration for him?” Bookwalter pressed. “That is correct.” “As you sit here today, don’t you take an equal share of blame for this?” “Definitely.” “You’re not trying to place it on him?” “Believe me,” Nathan replied, “it is not easy to try and push blame on a man who is dead. I did not want to throw blame on another. It is not an attractive thing to do, but I must answer the question honestly.”

But Bookwalter was still not satisfied. Nathan seemed to want it both ways – he wanted to express remorse but still deny that he had a meaningful role in the murder. Bookwalter knew the case. He’d read all the transcripts. He pressed again, “You are taking an equal share of the responsibility?”

“Very definitely.” “I understand there were articles used in this crime purchased by you and stored in your house?”

“My share was equal,” Nathan replied cautiously, fearing that his parole was about to be denied yet again.

Bookwalter suddenly changed the subject. He asked Nathan if he knew that if the board granted him parole that this meant he had to avoid all television and radio appearance? Did he understand that he was not to give statements to the newspapers? Every media outlet in the country would want an interview with him.

Nathan hastily replied, “I don’t want any part of lecturing, television, or radio, or trading on notoriety. This is the last thing… All I want, if I am so lucky as to ever see freedom again, is to try to become a humble little person.”

On February 20, 1958, the board announced that they had agreed to parole Nathan Leopold. He was released three weeks later, on March 13. He walked out of Stateville to confront a mob of newspaper reporters, television crews, and photographers. He looked around nervously as they shouted questions at him. His voice quavered as he spoke into a microphone: “I appeal as solemnly as I know how to you and your editors, to agree that the only piece of news about me is that I have ceased to be news. I beg, I beseech you and your editors and publishers to grant me a gift almost as precious as freedom itself – a gift without which freedom ceases to have much value – the gift of privacy. Give me a chance – a fair chance – to start life anew.”

It was a meaningless appeal. The crowd pushed forward, shouting again. Elmer Gertz gently pushed Nathan away from the microphone and toward a waiting car. Its engine was running, and the driver was ready to make a quick exit. The reporters immediately reacted, rushing to their own cars so that they would not be left behind.

Nathan was taken towards Chicago, running with scores of other cars in pursuit. Ralph Newman, one of his closest friends, had offered his home in Oak Park, west of the city, as a temporary refuge. But, within minutes of his arrival, Nathan looked out a window to see dozens of reporters on the street. He was given a police escort into Chicago, where he planned to stay at an apartment on Lake Shore Drive with a college friend, Abel Brown.

But it became impossible for him to stay even a few days in the city. He had hoped to visit the graves of his parents, but journalists had discovered his hiding place and camped outside, waiting for him to leave the apartment. He had no choice but to leave immediately. He had accepted the job in Puerto Rico and knew that only after he had left the United States would he find peace.

The tranquility of the town of Castaner, on Puerto Rico, was a welcome change from Chicago. High in the mountains, it was an idyllic spot. Nathan spent his days peacefully, working as a medical assistant in the hospital, enrolling as a graduate student in social work at the University of Puerto Rico, and making new friends.

But the past refused to leave him alone. Meyer Levin, a contemporary of Nathan and Richard at the University of Chicago, had written a novel called Compulsion, based on the murder. The book was overwrought, exaggerated, outlandish, and the character based on Nathan was far from flattering. Now Nathan learned that Twentieth Century Fox was making a film of the novel, starring Orson Welles. Nathan decided that this was an invasion of his privacy and in October 1959, he instructed Elmer Gertz to file suit against Levin and the film production company, Darryl F. Zanuck Productions, for the “appropriation of the name, likeness, and personality of Leopold and conversion of same for their profit and gain.”

To most people, the lawsuit seemed insane. One of the most notorious murderers in American history was now complaining that a fictionalized account of the crime appropriating his name? Leopold had filed suit for $1.4 million in court. If he collected, would he not, in fact, profit from his crime? Meyer Levin, who had publicly supported Nathan’s parole, was indignant that his generosity was rewarded with such ingratitude.

The case wound its way endlessly through the courts, eventually reaching the Illinois Surpreme Court in 1970. There, it was finally dismissed. Meyer Levin spent tens of thousands of dollars in his defense. In the decade of legal wrangling over the case, no publisher would reissue Compulsion after its initial print run for fear of incurring damages if the courts decided in favor of Nathan.

While the lawsuit was taking place in Chicago, Nathan was still living peacefully in Puerto Rico. Not long after his arrival on the island he met Trudi Feldman, 53, a woman from Baltimore who was the widow of a physician. In October 1961, after obtaining permission from the parole board, the two were married in Castaner. They lived comfortably on Nathan’s sizable inheritance, which had accumulated interest while he was in prison, and Trudi opened a flower shop in San Juan.

In 1963, Nathan was released from his parole, allowing him to drink alcohol, drive a car, stay out at night, and travel outside of Puerto Rico. Neither Trudi nor Nathan had seen much of the world, so they traveled widely in the 1960s, visiting Europe, South America, Asia, and the Middle East. Nathan returned to Chicago often, to see old friends, visit his old neighborhood, and place flowers on the graves of his parents and two brothers.

The murder of Bobby Franks had passed into legend. It had become a sort of catchphrase – the “Leopold and Loeb case” – and it periodically popped up in books and in newspapers as time moved on.

Nathan wrote his own account of the story in a book called Life Plus 99 Years and continued to be hounded by the press for his role in the “perfect murder” that he had committed decades before. He stated that he would be “haunted” by what he had done for the rest of his life. He died of a heart attack on August 29, 1971, bringing his story to an end.

It also brought an end to another story that had been taking place since 1924 – a sadder and much more tragic one than the alleged rehabilitation of Nathan Leopold.

The conviction of Nathan Leopold and Richard Loeb did not, according to many people, bring an end to the terrible case of Bobby Franks. This belief has been supported by the accounts of a restless spirit that continued to walk for many years after the two killers were safely locked behind bars. That spirit, the accounts stated, was Bobby Franks, who took nearly 50 years to find peace.

During those decades, visitors to Rosehill Cemetery on the north side of Chicago often reported seeing the ghost of a young boy standing among the stones and mausoleums in the Jewish section of the graveyard. It is there where the Franks family mausoleum is located, although its location is not listed on any maps of the cemetery and employees are instructed not to point it out to curiosity-seekers. This is a tradition that dates back all the way to the 1920s, when the family so desperately wanted to avoid publicity from daily stories that appeared in every newspaper in the city.

Even so, people found the tomb within the confines of the beautiful burial ground, and starting in the late 1920s, maintenance workers and visitors alike encountered the ghostly boy. It was, they all believed, the spirit of Bobby Franks, unable to rest in the wake of his bloody and violent death – and perhaps restless because he did not feel that justice had been served in his case.

The boy continued to be seen wandering for years. He was always reported from a distance, though. Whenever he was approached, the apparition would vanish. These sightings continued for years, but eventually, they came to an end – in 1971.

Encounters with Bobby’s spirit ended at almost exactly the same time that Nathan Leopold died in Puerto Rico. Coincidence? I’d prefer to think that it’s not. I’d like to think that it means that poor Bobby Franks was finally able to find some peace on the other side.



Thanks for listening. If you like the show, please share it with someone you know who loves the paranormal or strange stories, true crime, monsters, or unsolved mysteries like you do! You can email me anytime with your questions or comments at darren@weirddarkness.com. WeirdDarkness.com is also where you can find all of my social media, listen to free audiobooks I’ve narrated, visit the store for Weird Darkness t-shirts, hoodies, mugs, phone cases, and more merchandise, sign up for monthly contests, find other podcasts that I host, and find the Hope in the Darkness page if you or someone you know is struggling with depression or dark thoughts. Also on the website, if you have a true paranormal or creepy tale to tell, you can click on TELL YOUR STORY. You can find all of that and more at WeirdDarkness.com.

All stories in Weird Darkness are purported to be true (unless stated otherwise) and you can find source links or links to the authors in the show notes.

”The Perfect Murder of Bobby Franks” by Troy Taylor – from the book “Suffer the Children: American Horrors, Homicides and Hauntings”. You can get the Kindle or paperback version now on Amazon, and the audiobook version is also available, narrated by Yours Truly. You can find a link to the book in the show notes.


WeirdDarkness® – is a production and trademark of Marlar House Productions.

Now that we’re coming out of the dark, I’ll leave you with a little light… “Let us not become weary in doing good, for at the proper time we will reap a harvest if we do not give up.” – Galatians 6:9.

And a final thought… “If we think we can overcome our fears, we will do so.” – Marcos Witt

I’m Darren Marlar. Thanks for joining me in the Weird Darkness.



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