Leopold and Loeb: The not-so-perfect crime

The following post contains descriptions of violent crime against a child and adult themes. Discretion is advised.

On Wednesday, May 21, 1924, in the wealthy South Chicago neighborhood of Kenwood, 14-year-old Bobby Franks disappeared while walking home from school. That evening, his worried parents, Jacob and Flora Franks, got a call from a man who identified himself as George Johnson, telling them that their son had been kidnapped and that they would receive demands for his safe return the following day. 

In the next day’s mail, there was indeed a typed letter with instructions. The kidnappers were demanding 10,000 dollars – a little over 160,000 in 2022 money. The letter warned that any deviation from the instructions or involvement of authorities would result in Bobby’s death. The letter was signed “George Johnson.” That afternoon, Jacob Franks received another call from George Johnson, notifying him that a taxi was on its way to his house and that he was to go to the Vander Bogart & Ross Drugstore on 63rd Street for further instructions. Jacob, in his distress, forgot the address of the store and could not go.

But that turned out to make no difference; Bobby Franks’ body was found that day at a nature preserve at Wolf Lake, about 40 miles southeast of Chicago, right by the Indiana state line, having been hit on the head several times with a blunt object. The body was nude and had been half-stuffed into a culvert. Acid had been poured over his face in an unsuccessful attempt to obliterate his features and prevent him from being identified. Near the boy’s remains was found a sock, which belonged to Bobby–and a pair of tortoise shell glasses that did not. 

Bobby Franks

Immediately authorities began looking for people who were known to go to Wolf Lake, especially people who wore glasses. One person who came to their attention was Nathan Leopold Jr, a 19-year-old graduate student at the University of Chicago. Leopold came from a wealthy and well-respected German-Jewish family, and was a prodigy: he had been skipped several grades in school and, while most other 18-year-olds are just starting university, he had graduated after only three years. At the time Leopold spoke at least 15 languages, and he was also an avid and nationally recognized ornithologist (someone who studies birds). He was a regular at Wolf Lake. Police did not consider him a suspect, but someone who might be able to help by providing information about other people who were familiar with the preserve. He said that he no longer wore glasses, and that the last time he had been to Wolf Lake was May 17th, the Saturday before Bobby’s disappearance and murder. 

The authorities focused on the small, round glasses now in their possession. There was nothing unusual about the frames – spectacles like these were sold all over Chicago every day. And the prescription was for very mild astigmatism, also not uncommon. But what WAS uncommon were the hinges on the glasses. They were newly patented and, when police asked occulists around the Chicago area to check their sales records, they found that only three people had purchased glasses with these particular hinges. The first person was in Europe, and the second person had her glasses on when she answered the door to police. The third pair had been sold to Nathan Leopold Jr. 

Leopold was brought in for questioning again, this time by State’s Attorney Robert Crowe and his assistants. And this time he was being looked at as a suspect. Nathan accepted that the glasses must be his after all, and that he must have lost them the last time he was at Wolf Lake the previous Saturday (May 17th). The thing was, it had rained at Wolf Lake the following day, and yet the glasses were dry and clean, which they would not have been if they had been there when it had rained… meaning he had been there more recently than he was claiming.

When Nathan was asked what he had done Wednesday afternoon and evening, he claimed that he and his friend Richard Loeb had gone birdwatching, had dinner, and that night picked up a couple of girls and drank with them. The authorities immediately went to bring in 18-year-old Richard Loeb, son of Sears Roebuck vice president Albert Loeb and Nathan Leopold’s best friend. Dick Loeb, being questioned separately, contradicted his friend’s story, claiming that he went home after dinner and didn’t remember what he did the rest of the evening. Eventually, however, he too corroborated the story about drinking with the girls. The more the assistant state’s attorneys questioned the boys, the more convinced they became that the pair were lying and were involved in the murder of Bobby Franks. But they did not have enough to charge them. They could not hold the sons of wealthy and connected families much longer without more evidence and would have to let them go.

But then the police received a visit from Sven Engund, the Leopold family’s chauffeur. Englund claimed that the boys could not have been involved in the crime, since Nathan didn’t even have his car — Englund had been working on Nathan’s red Willys-Knight all afternoon and early evening to fix squeaky brakes.

Instead of clearing the boys, the well-meaning chauffeur had unwittingly destroyed their alibi. Dick Loeb cracked when confronted with the giant hole in their story, and confessed that he and Nathan had lured Bobby Franks into a rented Willys-Knight and that he died after being bludgeoned with a chisel (they had also stuffed a gag into his mouth, which suffocated him). Dick claimed that Nathan was the actual murderer while Dick was the driver. Nathan Leopold only confessed after the authorities proved to him that Loeb had squealed, but he vehemently denied that he had wielded the weapon and claimed that he was driving while Dick had bludgeoned Bobby in the backseat of the rented Willys-Knight. We technically don’t know to this day which one actually killed the boy, but evidence and most experts agree that Nathan was driving and that Dick was the actual murderer. Dick was known to be a pathological liar, and Nathan appeared to have no criminal tendencies on his own part; he was only involved to please Dick and to prove some intellectual superiority experiment.

Now began one of the most high-profile murder cases of the early 20th century. Famed attorney Clarence Darrow was taken on to defend Dick and Nathan, and along with Walter and Benjamin Bacharach. The boys had already confessed, so they weren’t walking away free men. The defense team’s job was therefore merely to keep them from the hangman’s noose. They did this by doing something that had never really been done before: bringing up their psychological problems without claiming insanity, which they knew would never fly. The boys pled guilty to avoid a jury, essentially turning what would have been a trial into a hearing. the boys’ fates would lie in the judge’s hands alone. Darrow knew that a jury would most likely recommend death, and it would also give the prosecution the opportunity to seek the death penalty for the kidnapping, since kidnapping in and of itself was a capital crime.

During the hearing, which commenced in June of 1924, the almost unbelievable backstory behind the horrible crime gradually emerged: Nathan and Dick were not just friends, but lovers. They had met in their first year at the University of Chicago at the ages of 15 and 14 respectively, and quickly became close. Dick was classically handsome and charming, but had sociopathic tendencies; he fantasized about being a great criminal. Nathan was small, a little awkward-looking, and far more introverted. He was also homosexual, and hopelessly in love with Dick. They had an arrangement, informal at first, that Nathan would serve as Dick’s accomplice in his petty crimes and in return Dick would give Nathan sexual favors.

Nathan Leopold (left) and Richard Lob (right) in court

In November of 1923, they decided to up the ante and commit a crime that would make headlines. Nathan was obsessed by Friedrich Nietzsche’s idea of “the superman”, men who were above the morals and rules of the masses. The boys set out to prove that they were “supermen” who could commit the perfect crime and get away with it. They decided on kidnapping a local wealthy kid, killing him to eliminate the risk of him going to the police, and getting ransom from the parents. In May of 1924, the plan was set in motion. They some boys in mind, but hadn’t decided on any in particular; it was simply Bobby Franks’s misfortune to be spotted by the pair while walking home alone from school that afternoon and that he accepted their offer of a ride home; Dick was actually his second cousin as well as a neighbor, so Bobby wasn’t wary. They had rented a car to commit their nefarious deed, using a fake identity they had established by opening a bank account and renting a hotel room in that name.

Top: the Underwood Standard Portable 3-bank typewriter that was used by Nathan Leopold to type the ransom note. He and Loeb had twisted off some of the keys before throwing it into a lagoon in Jackson Park a few nights after the murder. The lagoon was dragged, and the typewriter was recovered. Bottom: I found and bought the same exact model typewriter on Ebay for $100. and it it sits in my bookcase.

On September 10, 1924, after an impassioned speech given by their lawyer Clarence Darrow, Nathan Leopold Jr. and Richard Loeb were sentenced by Judge John Caverly to life in prison for the murder plus 99 years for the kidnapping at Joliet Penitentiary, with a strong admonition that they should never be considered for parole. He stated that the only reason he had not sentenced them to death was because they were not of age (21), but he had given them the next harshest sentence he could.

Over the next six years, Dick and Nathan were kept apart as much as possible. When a new and far nicer prison was built a year after their sentence began in 1925, which became known at Stateville, Nathan was sent there. He campaigned to get the warden to allow Dick transfer to Stateville as well, and in 1931 that happened. The two celled in the same block, though they were not cellmates, and eventually began a prison correspondence school together for the inmates. Dick was the director, teaching English and history, while Nathan taught math and foreign languages. 1931 to early 1935 were probably the happiest years Nathan spent while incarcerated. Their fathers had both died within five years of them going to prison, Dick’s only one month after and Nathan’s in 1929.

But on the morning of January 28, 1936, after chatting and grading papers together over breakfast, Dick Loeb was attacked in the shower with a razor by another inmate, James Day. He was brought to surgery but died on the operating table three hours later. Nathan was by his side, having rushed to the operating room at the news of what had happened. Nathan was absolutely devastated, and actually spent the next six months being treated for depression and residing in the “bug ward” (early 20th century prison term for the psych ward). He refused to testify against James Day, fearing retaliation. He also he reasoned, in his words, that doing so would not have brought Dick back. Nathan eventually returned to teaching, taking over as the director of the prison school and dedicating it to his late best friend; he never completely recovered from his loss. He eventually got bored with teaching and became an x-ray technician and even headed up an anti-malaria research project during the Second World War (the parasitic infection was killing more soldiers in the Pacific than the enemy Japanese soldiers were). He even had himself deliberately infected to test the effectiveness of the medication they were developing.

Nathan thought this research might offer him a chance at parole after all, but his first request in 1953 was denied. A few years later, in 1957, he wrote a prison memoir called Life + 99 Years, in which he discusses his experiences since his sentence began–he avoids mentioning the murder much, or his life before September of 1924–and in which he expresses remorse for his crime. His second request in 1958 was granted, and he immediately moved to Puerto Rico; he knew that he would never be left alone if he remained in the United States. He got a Master’s Degree in social work in 1961 and got married the same year (yes, to a woman). He and his wife Trudi spend the next ten years together taking in dogs, traveling, once Nathan’s parole ended, and doing many charitable works. Nathan seemed determined to try to be remembered for the good things he did rather than for the 1924 murder in which he took part. He died of a heart attack on August 29, 1971.

The Leopold and Loeb case was one of the most fascinating I’ve come across, inspiring many books and movies that are based upon it (my own book is a novelization about the case written from the perspective of Nathan Leopold). The murder was the least interesting aspect about the case, in my opinion, although certainly the most tragic — Bobby Franks should never be forgotten. But the circumstances that led up to the senseless crime and its aftermath are as strange today as they were 98 years ago.

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