Vintage Chicago Tribune: Leopold and Loeb

To the public, Robert “Bobby” Franks’ death 100 years ago appeared to have been orchestrated for money and for thrill.

But the two brilliant masterminds behind the crime simply referred to it as a “perfect murder” — for which they believed they could outsmart the authorities and would never stand trial.

Friends Nathan “Babe” Leopold Jr., 19, and Richard “Dickie” Loeb, 18, were the pampered sons of prominent Kenwood families.

The wealth in Leopold’s family stemmed from both his parents. His father, Nathan F. Leopold Sr., was a paper box manufacturer. His mother Florence, heir to a banking fortune, died several years earlier. A law student at the University of Chicago, Leopold claimed to be familiar with 15 languages, an atheist and a student of ornithology.

The ‘Crime of the Century,’ 100 years later

Eighteen-year-old Loeb made headlines in 1923 after becoming the youngest student to graduate from the University of Michigan in Ann Arbor. His father Albert, who had been an attorney and vice president of Sears, Roebuck and Co., rewarded his son’s collegiate success by constructing a miniature nine-hole golf course in the family’s backyard at 5017 Ellis Ave.

Both had access to the best education and material things money could buy in the 1920s — impeccable clothing, flashy automobiles and even fine wines and spirits during Prohibition. Yet their affluence would also lead to their downfalls.

Their crime inspired not only copycats but also dramatic adaptations including the 1929 play “Rope,” the 1948 Hitchcock film of the same name, Chicago-born author and reporter Meyer Levin’s 1956 novel “Compulsion” and its 1959 film version starring Orson Welles, Dean Stockwell and Bradford Dillman, and John Logan’s 1988 play “Never the Sinner.”

Other “crimes of the century” have come and gone, but Leopold and Loeb’s case continues to fascinate and infuriate generations of Chicagoans.

May 21-22, 1924: Relative becomes victim in ‘perfect murder’

Robert “Bobby” Franks, a student at the Harvard School for Boys at 4731 S. Ellis Ave., hesitated when a gray Winton car pulled alongside him and he was offered a ride home from school. The 14-year-old, however, had reason to believe it was OK to accept the offer — he was related to one of the car’s occupants. Franks was Loeb’s second cousin who lived just across the street. They often played tennis on the Loeb estate’s court.

“He said, no, he would just as soon walk, so I told him I would like to talk to him about a tennis racket, so he got in the car,” Loeb later said.

When Franks got into the car, Loeb subsequently recalled: “Leopold reached his arm around young Franks, grabbed his mouth and hit him with a chisel. He began to bleed and wasn’t entirely unconscious. He was moaning.”

In the hours that followed, Franks’ father got a $10,000 demand in a typewritten ransom letter and his mother answered a mysterious phone call from a man who identified himself as “Mr. Johnson.” The family had the funds — Jacob Franks had earned his fortune through businesses including a pawn shop, watch companies and in real estate. The newspapers quickly ballyhooed the boy’s death as “The Crime of the Century.”

“The English in the threatening letter was so good that it must have been written by a man of more than ordinary education,” the Tribune reported. Police began to suspect maybe an instructor at Franks’ school was responsible for his death. The letter also echoed themes that appeared in a story called “The Kidnaping Syndicate” in a recent edition of Detective Story Magazine.

Was Franks the intended target?

Armand Deutsch, a Chicago-born film producer, believed he was the intended target in the 1924 case. He claimed the men “cruised around the Harvard School looking for me or another acceptable candidate.”

“It was no mystery why Richard Loeb and Nathan Leopold had singled me out as a prime prospect for their heinous crime,” Deutsch wrote in 1996 for the Chicago Tribune Magazine. “My grandfather, Julius Rosenwald, was the chairman of the board of Sears, Roebuck and Co. His prominence made me an ideal choice.”

Armand Deutsch

“In addition,” he wrote, “Loeb’s father was a Sears vice president. Our families were friends. … So I knew and trusted both older boys, a great plus as they formulated their plans for what would become the first ‘crime of the century.’”

Instead of himself, Deutsch wrote, they “found my 14-year-old schoolmate Robert Franks. Like me, Bobby knew and trusted both of them.”

“How had I avoided certain death?” Deutsch wrote in the Tribune. “My daily routine was to walk home from school. Had I followed it on May 21, I surely would have accepted (the) invitation for a ride. Instead, I was picked up by the family chauffeur for a dental appointment.”

May 21-22, 1924: Body disposed of then discovered — with an interesting clue

Leopold and Loeb drove Franks’ body to the Edgar Woods Forest Preserve near 118th Street and adjacent to Wolf Lake. En route they stopped at a restaurant and bought a pair of hot dogs and root beers.

After dark, they pulled off the road near the Pennsylvania Railroad’s tracks and a culvert.

“We dragged the body out of the car, put the body in the road and carried it over to the culvert,” Loeb later recalled. “Leopold carried the feet, I carried the head. We deposited the body near the culvert, and undressed the body completely.”


The morning after Franks’ murder, Tony Minke, a pump operator at the nearby American Maize Co., discovered a body at about the same time Franks’ father received the ransom letter. No connection was made between the disappearance of Franks and the body, however, until that evening. Despite the blows to his head, doctors believed Franks died from suffocation — but not without a struggle.

One clue was found at the scene — a pair of horn-rimmed eyeglasses. Though the spectacles were the right size for Franks, his father said the child never wore glasses.

May 30-31, 1924: With alibi shaken, Leopold and Loeb confess

A week after Franks’ murder, investigators were still trying to piece together who might be responsible for the crime. Tribune reporter Maurine Watkins, who would later write the play that became the Broadway hit “Chicago,” followed the Franks family as they said goodbye to their son in Rosehill Cemetery.

Then, a slip of the tongue pointed all eyes on Leopold. He admitted to owning a similar pair of the rare, expensive glasses as those discovered near Franks’ body — and losing them at the same spot while birdwatching a few days earlier. Further questioning connected him as owner of the typewriter on which the ransom letter was typed. When Leopold could not produce either item, he became a suspect. His friend Loeb was also questioned by police.

Both men claimed they took a Leopold family car for a joyride that night, but their alibi fell apart when the family’s chauffeur said the vehicle was in the garage the day of Franks’ murder.

The “perfect murder” Leopold and Loeb thought they had constructed actually left investigators with no other suspects but them. With the retrieval of Leopold’s typewriter from a harbor in Jackson Park, the chain of evidence that connected the two young men to the crime was complete. Both confessed to killing Franks.

July 21, 1924: Darrow’s defense — ‘I am pleading for the future’

Some figured Leopold and Loeb’s trial would hinge on an insanity defense. In Illinois, the legal definition of insanity was a defendant’s inability to understand the charges he faces. Acting or talking crazy didn’t count, and Cook County State’s Attorney Robert E. Crowe said his psychiatrists would testify that Leopold and Loeb were in full possession of their mental faculties.

Clarence Darrow was hired by the confessed killers’ families for their defense. He made a surprise tactical move as the trial began.

“We withdraw our plea of not guilty and enter a plea of guilty,” Darrow told Judge John Caverly.

By entering guilty pleas, Darrow didn’t have to persuade 12 jurors to spare his clients the hangman’s noose. In a trial’s sentencing phase, the judge has the ultimate say.

Clarence Darrow’s words, if not his ghost, still linger in Jackson Park

After the evidence had been presented, Darrow addressed the judge, speaking for 12 hours over two days.

“Your honor stands between the past and the future. You may hang these boys; you may hang them by the neck till they are dead. But in doing it you will turn your face toward the past,” Darrow said. “I am pleading for the future.”

Darrow’s eloquent plea had the desired effect. Leopold and Loeb were sentenced to life in prison.

Sept. 11, 1924: Off to prison

A caravan of vehicles transported Leopold and Loeb to Joliet where they would become convicts No. 9305 and No. 9306 in Illinois’ penal system.

The pair were greeted by a mob of reporters, photographers, guards armed with rifles and spectators just outside the penitentiary’s gates.

Would you buy Leopold and Loeb’s fingerprints? A famous murder weapon? Chicago museums sometimes face similar questions.

“The great lock in the center door clanked as the key was turned,” the Tribune reported. “The iron barricade separating the 1,500 convicts from the great outside swung slowly on its hinges.”

Reporters hoping for a last word before the men entered the prison got this statement from Leopold:

“It’s 1924 now; it will probably be 1957 when we get out, and I’ll have a beard so long,” he said.

Jan. 28, 1936: Loeb slain in Stateville

James Day, a Chicagoan who was serving a prison term of up to 10 years for grand larceny, confessed to slashing Loeb 56 times with a razor in a shower room at the prison in Joliet. Day, who claimed the act was in self-defense after Loeb had tormented him for months, was acquitted by a jury for Loeb’s death on June 4, 1936.

Loeb’s death sparked a statewide investigation of conditions in Illinois prisons, which lampooned every facet of the penal and parole system and preferential treatment for inmates — like Loeb — with unlimited funds. Leopold and three other Stateville prisoners were questioned as part of the inquiry, but didn’t provide details about what led to Loeb’s death.

Feb. 20, 1958: Leopold granted parole

In his parole appeal, Leopold said he was “an intelligent savage” at the time of Franks’ murder, which he claimed Loeb had led him into. Leopold said his lack of moral sense was due to his accelerated intellectual development — at the sacrifice of a normal teenage experience. When asked by the parole board why he joined in the murder, Leopold said that Loeb was his best friend — but also his worst enemy — though he immediately noted that he was equally guilty for the crime.

“I literally lived and died in his approval and disapproval,” he said. “I would have done anything he asked. He wanted very badly to do this terrible thing. He had spent years reading detective stories. I had no desire to do it. On the contrary, the idea was repugnant to me. Loeb made sure we would actually do it. I couldn’t back out of the plan without being a quitter — forfeit Loeb’s friendship.”

Despite Pulitzer Prize-winning Abraham Lincoln biographer Carl Sandburg’s speaking on behalf of his release, Leopold vowed to avoid all publicity and reject radio and television offers if granted freedom (though Doubleday did release his autobiography, “Life plus 99 Years,” which Sandburg endorsed as a Christmas gift suggestion).

“All I want is to get out of the spotlight,” he said. “Gentlemen, you see before you today not the conceited smart-alecky kid of 34 years ago. I’m an old man, a broken old man who humbly pleads for your forgiveness.”

Leopold was released from Stateville on March 13, 1958 — the 20th anniversary of Darrow’s death — and driven back to Chicago. But it wasn’t an easy commute. Leopold, who had suffered from car sickness since he was a child, had to pause several times during the road trip because he was “violently ill,” the Tribune reported.

The next day he departed for Puerto Rico, where he would earn $10 per month working as a laboratory and X-ray technician at a mission hospital. He married Trudi Garcia de Quevedo, a flower shop owner, on Feb. 7, 1961, and earned a master’s degree in social work a few months later. He was discharged from parole on March 13, 1963, and spent part of that summer visiting Israel, Greece and Europe with his wife before returning to Chicago to attend a conference on tropical medicine. He also visited his collection of birds, bugs and fish at a museum in Elgin. In the only interview given during his stay, Leopold told reporters he was against capital punishment, favored penal reform and considered himself a pacifist.

Leopold died in Puerto Rico on Aug. 29, 1971, at the age of 66.

October 1985: ‘We thought the file had been stolen’

The long lost file of the Leopold and Loeb case was unearthed in a box in a dusty corner of the records center kept by Cook County Circuit Court Clerk Morgan M. Finley.


Finley discovered the box while reorganizing the office’s 25 million files, which occupied 41 miles of shelves in a building at 23d Street and Rockwell Avenue, and placed it next to the Haymarket Square riot documents and the Black Sox case in his office.

“We thought the file had been stolen by souvenir hunters when they were filming the movie ‘Compulsion,’ ” a source told the Tribune.

July 17, 2018: ‘One of America’s Most Infamous Crimes’ captured in book

Archivist Kevin Leonard also discovered a trove of Leopold and Loeb case files — including the ransom note written by the pair, their confessions and court transcripts — in the basement of Northwestern University’s Law School in 1988. The collection was catalogued then exhibited in 2009, to an enthusiastic crowd of local history buffs and true crime aficionados.

Vaulted reputations

The exhibition’s success prompted its curator and author Nina Barrett to compile photos and ephemera into a bound edition — “The Leopold and Loeb Files: An Intimate Look at One of America’s Most Infamous Crimes.”

There was a bit of legal wrangling involved in getting the book to press, however, Tribune columnist Rick Kogan wrote in 2018: “That began in 2014 when NU initiated the federal suit against Barrett, who had been employed by the university, claiming she took an unfinished manuscript and related files after she quit her job and had refused to respond to its demands to return those files. After more than a year, Northwestern and Barrett agreed to share ownership of the copyright.”

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