When Bobby Franks was 14 years old, he delivered an impassioned indictment of capital punishment during a school debate competition, arguing that “only God is permitted to take human life.” Asked whether this stance contradicted the principle of “an eye for an eye,” he replied, “Punishment should be reformative, never vindictive.”

Franks’ rhetoric impressed the contest’s judges, who declared his team the winner. Just two weeks later, the debate champion would be dead, the victim of a murder that captivated the nation and raised lasting questions about the very issue that Franks had just debated.

On the afternoon of May 21, 1924, Franks came across 18-year-old Richard Loeb, an acquaintance he sometimes played tennis with, while walking home from school in Chicago. Loeb offered Franks a ride in his car, but the boy declined, as he was just a few blocks from his destination. “Come on,” Loeb reportedly said. “I want to talk to you about the tennis racket you had yesterday. I want to get one for my brother.” Franks relented.

The next morning, a Polish immigrant found Franks’ nude body stuffed into a drainage culvert about ten miles away. Far from a whodunit, Loeb and 19-year-old Nathan Leopold confessed to the murder ten days later, after they became leading suspects. In police interviews, both men admitted the crime was committed merely for the thrill of it all.

A newspaper article about Franks' murder by Leopold and Loeb
A newspaper article about Franks' murder by Leopold and Loeb The New York World

Newspapers at the time offered a range of alternative theories for the grisly murder, from the young men’s privileged upbringing to their atheist beliefs to their college curriculums. As Erik Rebain, author of Arrested Adolescence: The Secret Life of Nathan Leopold and the creator of a website dedicated to the case, says, the public started seeking answers to recurring questions: “Why did this happen? How could these people have turned into this? … Anything you wanted to blame [the murder] on, you could blame it on.”

Thanks in large part to nonstop media coverage, the relatively straightforward hearing (Leopold and Loeb pled guilty, so they didn’t face a trial by jury) became a mirror for the anxieties of the 1920s, allowing observers to attribute the crime to whatever they perceived as society’s ills. This fascination endures a century later.

“The reason that this case continues to grab people when there have been so many other sensational murders is that the motive just has never been comprehensible to anybody else,” says Nina Barrett, author of The Leopold and Loeb Files: An Intimate Look at One of America’s Most Infamous Crimes. “Nobody has ever understood why two well-educated, privileged boys with a great future ahead of them … would think the most fun thing they could do on a spring afternoon would be to murder a kid from the neighborhood.”

Plotting the imperfect crime

Born into wealthy Jewish families in Chicago in 1904 and 1905, respectively, Leopold and Loeb were afforded every opportunity throughout their youth. Both were precocious students, with Leopold demonstrating a penchant for languages and ornithology, and Loeb preferring literature and history. Though the two grew up in the same neighborhood (as did their victim, Franks), they only became friends in spring 1920. The following February, the pair’s friendship turned sexual, “and they also started committing crimes together,” says Rebain. “You see this escalation in their relationship,” from petty theft to arson to perhaps even assault.

Loeb was the “gregarious and sociable” foil to Leopold’s “misanthropic and aloof” personality, writes historian Simon Baatz in For the Thrill of It: Leopold, Loeb and the Murder That Shocked Jazz Age Chicago. Though scholars generally agree that Loeb was the instigator of these crimes, some place more of the blame on Leopold’s shoulders. Loeb “seems to have had a big fantasy world in which he was rebelling against his parents,” says Barrett. “Instead of becoming the perfect, well-dressed, rich attorney they wanted him to be … he was becoming the opposite of that: the secret bandit, killer, lawbreaker.”

Loeb and Leopold
Loeb (left) was the “gregarious and sociable” foil to Leopold’s (right) “misanthropic and aloof” personality, writes historian Simon Baatz in For the Thrill of It: Leopold, Loeb and the Murder That Shocked Jazz Age Chicago. Bundesarchiv, Bild 102-00652, via Wikimedia Commons under CC BY-SA 3.0

Leopold was more interested in lawbreaking as an intellectual exercise demonstrating his superiority. He was also eager to maintain his romantic relationship with Loeb, sometimes promising to act as an accomplice in exchange for sex.

In November 1923, the pair robbed Loeb’s former fraternity house at the University of Michigan. Leopold wanted to rob a second house, too, but Loeb was reluctant. Neither heist was particularly successful, and the friends fought bitterly on their drive back to Chicago. Ultimately, they agreed to carry out a kidnapping, ransom and murder scheme that would prove their genius and cement their bond at a pivotal moment in their relationship. Leopold was set to depart for Europe soon, and Loeb was eager to stall their separation.

The duo concocted a plan involving false identities with elaborate backstories and decoy bank accounts, a wad of cash thrown out the window of a moving train, and a killing method that would leave both equally culpable for taking a life. (They later abandoned the idea of strangling the victim with a rope, each pulling on one end until he was dead, but that didn’t stop Alfred Hitchcock from immortalizing the murder weapon in Rope, his 1948 thriller inspired by the case.)

Though the pair initially considered killing a former friend of Loeb’s, they decided to instead target a young boy, as he would presumably be easier to overpower and more likely to be unsupervised than a girl of the same age. The victim had to be wealthy enough to ensure his family could pay the ransom, and he had to live nearby so the killers could observe the mayhem their actions had provoked without attracting suspicion.

Rope (1948) Official Trailer #1 - Alfred Hitchcock Movie

The murder of Bobby Franks

Beyond this criteria, Leopold and Loeb left their choice of victim “completely up to chance,” says Rebain. Though they’d written up a list of potential targets and almost selected a different boy, they ended up taking “the most likely looking subject that came our way,” as Leopold later told authorities. Though it took some convincing by Loeb for Franks to join them in the rented automobile, he did so, then greeted Leopold, whom he’d never met before.

The killers’ accounts of what happened next are generally in agreement, aside from one main point of contention: Both Leopold and Loeb named the other as the one who dealt Franks the fatal blow, hitting him over the head with a taped chisel multiple times before stuffing a rag down his throat. (The general consensus now is that Loeb committed the murder while Leopold drove the car.)

After Franks was dead, the pair drove some distance away, stripped the corpse of its clothing (but didn’t abuse it in any other way) and waited until night fell, passing time by stopping for sandwiches and root beer. Under cover of darkness, they doused Franks’ body in hydrochloric acid to mask his identity, then hid the boy in a culvert near the Indiana border, in an area where Leopold sometimes went birding. On their way home, they mailed a typewritten ransom note demanding $10,000 in cash and called the Franks, telling their victim’s mother that her son “has been kidnapped [but] is safe.”

The carefully constructed scheme quickly fell apart from there.

Bobby Franks' father, Joseph (right), and older brother, Jack (left)
Bobby Franks' father, Joseph (right), and older brother, Jack (left) Bundesarchiv, Bild 102-00651A, via Wikimedia Commons under CC BY-SA 3.0
Bobby Franks
Bobby Franks Public domain via Wikimedia Commons

The ransom letter, which arrived the following morning, advised the Franks family to “remain at home” after 1 p.m. and ensure “the telephone is not in use,” as the killers would provide further instructions via phone. But by the time Leopold and Loeb enacted the next step of their plan, the body had already been found. The hydrochloric acid had done little to disfigure the corpse. Newspapers covered the discovery of an unknown boy’s remains, announcing his identification as Franks—the son of a “retired millionaire manufacturer”—that same day.

The men had hoped Franks’ body would never be found, or at least not until decomposition had set in. The remains’ rapid recovery prevented the pair from collecting the ransom.

Over the following week, local and national papers alike speculated on the killer’s motive (the Chicago Tribune theorized that a sexual predator had “sought to cloak his act and the boy’s presumed accidental death by the demands for money,” while the Boston Globe posited that Franks had died while fighting off his kidnappers) and character (only a “scholarly person, a master of English,” could have written a ransom letter with such “faultless” grammar, according to the Tribune).

Another flaw in the plan came about when, in the killers’ haste to hide the body in the culvert, Leopold’s horn-rimmed glasses fell out of his pocket. This unassuming accessory proved to be the key to the investigation. It had a unique hinge that was only available through a single Chicago supplier. That company, in turn, had sold just three pairs of glasses featuring the patented technology. One belonged to a woman, while another was sold to a lawyer who was traveling in Europe at the time of the murder. The third belonged to Leopold, who readily supplied an alibi: He’d spent the day of the murder with his friend Loeb, driving around town before picking up a pair of young women.

Though Loeb presented a slightly different version of events, he soon changed his story to match up with Leopold’s, convincing the authorities—however briefly—of the pair’s innocence. But as investigators kept digging, they uncovered two damning pieces of evidence: Leopold’s maid had recently seen a typewriter like the one used to write the ransom note, though it had since disappeared from the family home. And Leopold and Loeb couldn’t have spent the day driving around in Leopold’s car, as his chauffeur was making repairs to it at the time. Confronted with these inconsistencies, Loeb confessed to the killing early on the morning of May 31. Leopold made a similar statement shortly after.

Mugshots of Leopold (top) and Loeb (bottom)
Mugshots of Leopold (top) and Loeb (bottom) Bundesarchiv, Bild 102-12794, via Wikimedia Commons under CC BY-SA 3.0
Leopold in jail
Leopold in jail in Cook County Bundesarchiv, Bild 102-10970, via Wikimedia Commons under CC BY-SA 3.0

The duo believed themselves to be “supermen” whose superior intellect placed them above the law. The murder, then, was a test of sorts, offering Leopold and Loeb a chance to prove their mettle by committing the perfect crime. But the plan’s spectacular failure only underscored their naïveté and immaturity.

“They planned some things so thoroughly, like making these false identifications and registering in different hotels and banks and all this background stuff that didn’t end up mattering at all,” says Rebain. “What got them were these little things that they just didn’t think about enough.”

The “trial of the century” that wasn’t a trial at all

Prosecutor Robert Crowe was determined to hang Leopold and Loeb. The public was similarly eager to punish these rich upstarts, who expressed little remorse for their actions. “We were experimenting” to commit the perfect crime, Leopold told reporters. “The killing was accidental and incidental. But it is as easy to justify such a death as it is to justify an entomologist impaling a beetle on a pin.”

As Crowe prepared to mount a case against the killers, their families sought out the best attorney money could buy: Clarence Darrow, who’d made a name for himself as a labor lawyer and would soon achieve great fame through his defense both of Leopold and Loeb and of John Scopes, the teacher at the center of the 1925 Scopes “monkey trial.” According to a biography of Darrow, a group led by Loeb’s uncle knocked on the Chicago-based attorney’s door in the early morning hours of June 2 and begged him to “save our two boys. … Get them a life sentence instead of a death sentence.” Darrow, a staunch critic of the death penalty, agreed to take the case.

Clarence Darrow, defense attorney for Leopold and Loeb
Clarence Darrow, defense attorney for Leopold and Loeb Public domain via Wikimedia Commons
A newspaper article about the key figures in the Franks case
A newspaper article about the key figures in the Franks case The San Francisco Examiner via Newspapers.com

Leopold and Loeb underwent extensive physical and psychiatric evaluation while awaiting trial—a fact that led many observers, including the prosecution team, to believe that Darrow would argue they were not guilty by reason of insanity. Instead, the attorney changed the pair’s plea to guilty.

Darrow’s shift in strategy reflected his belief that Judge John Caverly, who had a reputation as one of the court’s more liberal justices, would find it much harder to order the executions of two teenagers than a jury of angry Chicagoans would. By pleading guilty, Leopold and Loeb would not be judged by a dozen of their peers, but by one judge in a sentencing hearing. “I know perfectly well that where responsibility is divided by 12, it is easy to say, ‘Away with him,’” the attorney said in court. “But, your honor, if these boys hang, you must do it. There can be no division of responsibility.”

In making his decision, Darrow urged Caverly to consider three mitigating factors: the pair’s youth, their guilty plea and their mental state. Leopold and Loeb may not have been insane, the defense argued, but they were certainly mentally ill, plagued by “emotional immaturity, obsessions with crime and Nietzschean philosophy, alcohol abuse, glandular abnormalities, and sexual longings and insecurities,” writes Douglas O. Linder, a historian at the University of Missouri-Kansas City, on his Famous Trials website.

Psychiatrists detailed the killers’ childhood trauma, much of it inflicted by their strict upbringing. Loeb’s governess pushed the young boy to excel academically and discouraged him from socializing with other children, while Leopold’s “seduced him when he was still a child,” writes Baatz. “The damage inflicted on each boy at an early age had resulted in compensatory fantasies that led directly to the murder.”

The president of the American Psychiatric Association, William Alanson White, testified that Leopold and Loeb “complemented each other,” arguing that neither would never have committed the crime on his own. But the experts called to the stand by the prosecution offered a different perspective. Based on physical examinations of Leopold and Loeb, one neurologist said he had found no evidence of “any defect, any disorder, any lack of development or any disease.” The fact that two sets of psychiatrists came to entirely different conclusions led some observers to discount all of the expert testimony: Few realized that “each side spoke for a different branch of psychiatry”—the prosecution for neurology and the defense for psychoanalysis—“and was, therefore, separately justified in reaching its verdict,” writes Baatz.

Crowe and Darrow, the lead attorneys on either side of the case, also presented wildly varied portraits of the killers. The prosecutor referred to Leopold and Loeb as “cowardly perverts,” “snakes,” “spoiled smart alecks” and “mad dogs,” calling particular attention to the sexual nature of their relationship. “Leopold was willing to go along with Loeb because he could use his body for vile and unnatural practices,” Crowe argued. As remorseless killers who had taken a life in cold blood, the two deserved the death penalty, in his view.

Leopold and Loeb (second row) in court
Leopold and Loeb (second row) in court New York Daily News via Getty Images

Darrow, on the other hand, suggested that “these two very privileged sons of very wealthy families were actually victims,” said author John Farrell in a 2018 documentary about the case. “They were in this very sheltered life with cold families, and … they should be pitied rather than hated.”

The defense attorney traced the murder to the killers’ childhoods, arguing that their past experiences had determined the decisions they made as teenagers. “Somewhere in the infinite processes that go to the making up of the boy or the man, something slipped,” Darrow said. As a result, Leopold and Loeb could not be held fully responsible for their actions. Inflicting the death penalty on them would achieve nothing beyond satisfying the public’s bloodlust.

On August 23, approximately a month after the sentencing hearing began, Darrow delivered a closing argument that demonstrated both “his eloquence [and] his wit,” according to Barrett. Often appealing directly to the judge, Darrow used Leopold and Loeb’s case as a jumping-off point for a broader criticism of the death penalty. “We can learn, by reason and judgment and understanding and faith, that all life is worth saving, and that mercy is the highest attribute of man,” he said in the final minutes of his summation.

Crowe, in his closing arguments a few days later, countered by claiming that Caverly would put his “official seal of approval upon [Darrow’s] doctrines of anarchy” if he declined to sentence Leopold and Loeb to death.

A newspaper's illustrations of the Franks case
A newspaper's illustrations of the Franks case Muncie Evening Press via Newspapers.com

Caverly took nearly two weeks to reach a decision. When the court reconvened on September 10, the judge praised the lawyers’ “careful analysis” of Leopold and Loeb’s mental state and life histories as a “valuable contribution to criminology.” Still, despite the voluminous testimony provided by experts on both sides, Caverly’s decision ultimately came down to one chief consideration: the defendants’ youth. Instead of sending the pair to the gallows, he sentenced them to life imprisonment for murder and an additional 99 years each for kidnapping. Though Leopold and Loeb might welcome their reprieve from hanging, the judge pointed out that “the prolonged suffering of years of confinement may well be the severest form of retribution and expiation.”

Life plus 99 years

The public had breathlessly followed the story from the time of Franks’ kidnapping to the killers’ sentencing. Newspapers covered every development in the case, portraying Leopold and Loeb as “gentleman gangsters” at a time when Chicago was notorious for its mob activity, says Barrett. Everyone had an opinion on the pair’s motive: Editorials argued that if Leopold and Loeb had performed “physical labor as children, they wouldn’t have done this,” Rebain says. Other observers believed they’d been “overeducated” and shouldn’t have studied philosophy. Even the Ku Klux Klan weighed in, citing the friends’ German Jewish heritage as a reason for their depravity. In response to such criticism, Jewish rabbis pointed out that Leopold and Loeb were self-proclaimed atheists divorced from Jewish values.

On one front, however, the public was largely united: Leopold and Loeb should pay for their crimes with their lives, and the fact that they’d only received a prison sentence was a direct reflection of their money and privilege. People believed that “a poor defendant who couldn’t afford Darrow and all these psychiatrists … would just be hanged,” Rebain says. “They wouldn’t have any chance.” Others feared that crime would increase “because people think they can get away with anything.”

Loeb (left) stares at Leopold (right)
Historians generally agree that Loeb murdered Franks while Leopold drove the rental car. Hulton Archive / Getty Images

As for the three families at the heart of the case, none was particularly pleased with its outcome. Grateful as they were that Leopold and Loeb would not be hanged, the killers’ loved ones had to contend with the fact that these young men who had once shown such promise would now spend the rest of their lives in prison. The Franks, for their part, were ready to be out of the spotlight and able to grieve in peace.

“I always have seen [the case] as this sort of Shakespearean drama about these three families, [who] were all immigrants to America and had pursued the American dream,” says Barrett. The murder “basically ruined those families for generations,” she adds. It’s “a really tragic morality tale” about the limits of wealth and influence.

After the sentencing hearing wrapped up, Leopold and Loeb were imprisoned in Illinois’ state prison in Joliet. Leopold was transferred to the Stateville Penitentiary the following year, while Loeb remained at Joliet until 1930, when he reunited with his friend at Stateville. Initially, “they were in a lot of danger,” says Rebain. “Because they were 19, they were very young to be going to an adult prison. And because of the nature of their crime and the rumors about their sexuality … they were very much targets for assault.”

Both eventually adjusted to life in prison, particularly under the less restrictive conditions at Stateville, where they were “as close as it is possible for two men to be,” Leopold recalled in his autobiography. They collaborated to open a correspondence high school at the prison and often played handball and bridge together. Then, on January 28, 1936, another inmate by the name of James Day attacked Loeb in the prison shower, slashing him more than 50 times with a razor. “I think I’m going to make it,” Loeb reportedly told his doctors; Leopold, who’d rushed to his friend’s side after learning of the attack, offered to donate blood to Loeb but was turned down. Loeb died soon after at 30 years old.

Leopold (right) and Loeb (left) in Cook County jail in 1924
Leopold (right) and Loeb (left) in Cook County jail in 1924 Bettmann via Getty Images

Though Day claimed he’d acted in self-defense, fending off a sexual proposition by a razor-wielding Loeb, this explanation didn’t hold up to scrutiny, as Day suffered no injuries during the encounter and was the one who’d brought the weapon to the shower in the first place. A jury later acquitted Day of Loeb’s murder—a verdict that Rebain says was influenced by homophobia and lingering resentment of the victim’s earlier crime.

The murder sent Leopold, who declared Loeb both “my best pal” and “the greatest enemy I have ever had, for my friendship with him had cost me my life,” into a deep depression. It was only during World War II, when he volunteered for malaria studies conducted at the prison, that he found a renewed purpose. This verve for life happened to coincide with Leopold’s first opportunity to apply for parole, which was denied in 1953 amid intense public backlash but granted in 1958.

Leopold was released from prison on March 13, 1958, at age 53, after serving 33 years of his sentence. Eager to avoid the spotlight, he moved to Puerto Rico, where he’d received an offer of employment as a laboratory technician. While living abroad, Leopold earned a master’s degree in social work; married a former secretary; conducted medical research; and revisited his interest in ornithology, even publishing a book on the region’s birds. He died of a heart attack on August 29, 1971, at age 66.

A 1958 magazine cover featuring Leopold
A 1958 magazine cover featuring Leopold Public domain via Wikimedia Commons

Rebain decided to write his 2023 biography of Leopold after realizing that most accounts of the killer’s life dedicate just a few sentences to his experiences after parole. Diving into the archives, he found sources that contradicted the popular perception of Leopold as “the lesser of two evils, just a shy kid who had a crush on the wrong guy.”

In truth, says Rebain, Leopold’s correspondence paints him as a social, assertive figure who was “absolutely not letting anyone tell him what to do.” He bragged about violating parole restrictions against alcohol use, among other individual freedoms, and, in a letter to one of the attorneys who’d helped secure his release, claimed that he’d “visited most of the better whorehouses, cheap bars and gambling casinos in Greater San Juan.”

Casual observers often cited Leopold’s case as an example of the power of rehabilitation. After his death, Puerto Rican Governor Luis A. Ferré even declared that “the story of Nathan Leopold is one that must confirm the faith and intrinsic goodness of the human being.” But Rebain’s research suggests the killer wasn’t as reformed as many thought.

The Shocking Criminal Case of Leopold and Loeb (Full Documentary)

In the decades since the “trial of the century,” Leopold and Loeb’s story has inspired countless novels, movies, plays, documentaries and other adaptations. Reflecting on the case’s enduring appeal, Barrett points out that in 1924, the public was hungry for a kind of “tawdry sensationalism. Even though there were murders galore in Chicago … there wasn’t a murder among the rich people who should know better.” Today, says Rebain, the story contains “so many elements for people to latch onto, so even if you’re not interested in one aspect, you’re going to be interested in another,” whether it’s class, sexuality, religion or psychology.

Often forgotten in discussions of Leopold and Loeb is their victim, Franks. “He was a really smart kid,” Barrett says, and he showed “as much promise” as his precocious killers did. The author cites an anecdote shared by Franks’ father, who told reporters that his wife kept a copy of Franks’ winning argument against the death penalty in a box. Sometimes, she’d take the paper out and remind herself that her son wouldn’t have wanted his killers to hang for his death. “That was a source of comfort to her,” Barrett says. “The layers of tragedy in that, the amount of empathy in that one comment, is missing from anything Leopold and Loeb ever said, [and] it just kind of sums up why this is as big a tragedy as it is.”

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