Review: The Leopold and Loeb Files: An Intimate Look at One of America’s Most Infamous Crimes

Chicago has had its share of dynamic duos: Adler and Sullivan, Jordan and Pippen, Bozo and Cooky, Moo and Oink… Less dynamic and more demonic were Chicago killers Nathan Leopold and Richard Loeb, whose 1924 murder of Loeb’s second cousin, 14-year-old Bobby Franks, was dubbed the Crime of the Century. A term coined by 1900s journalists and attached to the highest of high-profile murders—think the Lindbergh baby kidnapping, Manson Family slayings, and O.J. Simpson—somehow Leopold and Loeb retain the title. With time’s passage their story has acquired an intangible, mythic quality. John Wayne Gacy is a fairy-tale ogre, Al Capone an outlaw legend, and Leopold and Loeb persist as urban folklore. Be careful when you walk home from school, kiddies. Else a pair of University of Chicago students may kidnap and murder you. Or something like that.

At one time I was a ravenous consumer of true crime literature, publishing a zine on the subject in the 1990s. My skin was thickly callused and I found L&L’s story tame beside more gruesome crimes. Yet they popped up in every murder anthology I came across, such is their hold on the public imagination. In the media and their own minds they were high-toned haut monde predators. Insidious criminal geniuses swooping down like peregrines in search of child victims, leaving not a trace of blood. Untraceable. Untouchable.

But they weren’t. Nope. Not at all.

Nathan Leopold

Considering the density of Nina Barrett’s The Leopold and Loeb Files, you’d think it was the definitive work on the case296 pages packed with information, presented in an eye-punishingly small font. But it’s not. Its more of an addendum of primary sources including court transcripts, confessions, psych reports, and interviews, that stresses facts over sensationalism. The book provides a more thorough and precise chapter in a well-worn tale, but it’s not a tale well told.

Well-off Kenwood teens Nathan Leopold and Richard Loeb were good friends, with impressive bona fides. Both U of C students, Richard graduated from the University of Michigan at age 18, while Nathan claimed to know 15 languages—though evidence suggests Loeb wasn’t that great a student and Leopold, while sharp, was a pedant and fabulist. Nonetheless, they had bright futures ahead of them.

But the ambiguously gay duo read one too many detective magazines and, like many a college student and/or Nazi, misinterpreted Nietzsche’s idea of the Übermensch. Deciding they were supermen themselves, they resolved to commit the perfect crime by murdering a child, demanding a ransom, and getting away scot-free. Well-read, the two young scholars forgot what happened to fellow, albeit fictional, murderer Raskolnikov of Crime and Punishment. He likewise thought himself exceptional and capable of evading prosecution for a double murder. Spoiler: there’s a reason why the book isn’t titled Crime and.

The murder itself was brutal. They lured Bobby to their rental car on the Gatsbyesque pretense of discussing a spiffing tennis racket Loeb owned. Leopold or Loeb (for a long time neither said who) dispatched Bobby with several chisel blows to the head, then they stuffed him into a culvert near Wolf Lake after dousing his face and body with acid to prevent identification. They needn’t have bothered. Franks has been historically obliterated since; just a footnote to L & L’s story. Rich kid on rich kid murder sold papers, of course, and the kidnaping, murder, and trial were an immediate sensation. Today poor Bobby would have had to be female and blonde to get as much coverage.

Richard Loeb

As it turned out, their perfect crime…was not. It took the cops a week to nab them, owing to Leopold dropping his easily traced spectacles near the body, an act more Clark Kentish than Supermanly. As mentioned, Leopold and Loeb’s families were loaded, and able to retain famed lawyer Clarence Darrow, who took the case out of his abiding interest in abolishing the death penalty. Pleading guilty and with Darrow backing them up, the two avoided being hung by the neck until they were dead, receiving instead 99 years plus life at Joliet Prison before moving to Stateville Penitentiary. They went the good behavior route, and started up a school for other inmates. Life happens, 10 years passed, and Loeb was attacked and carved up in the showers by a former cellmate. Leopold fared better, doing his time before receiving parole in 1958. Afterward, he moved to Puerto Rico, worked in a hospital as a medical technician, taught at the university, and published a bird-watching guide and his autobiography, Life Plus 99 Years, before dying in 1971. Bobby Franks, by all reports, remains dead in the Franks family crypt in Rosehill Cemetery.

As household names, Leopold and Loeb’s (always mentioned side by side) notoriety has faded outside of Chicago, though their crime inspired, directly or otherwise, a number of fictional psychopaths. Alfred Hitchcock’s Rope—known for its illusion of being filmed in real time with one tracking shot—starred Farley Granger and John Dall unconvincingly strangling someone their own size. With a rope. Much later, Richard Fleischer presented Compulsion, with the similarly alliteratively named murderers Steiner and Strauss, which more closely adhered to the circumstances of the crime. Much later, director Tom Kalin portrayed the boy-killers—undisguised this time—in 1990’s more gay-focused Swoon. Leopold and Loeb might have swooned to see themselves played by the sleek, sadistic, gleaming-in-tennis-whites family-killers of both versions of director Michael Haneke’s Funny Games, who (spoiler alert) blaze a trail of blood without dropping so much as a contact lens. Arguably, all killer couple films draw inspiration from one of two real-life homicidal duos depending on the relationship dynamic. If it’s a man and woman (Kalifornia, Natural Born Killers, Badlands), it’s Charles Starkweather and Caril Ann Fugate. But for a murderous male folie à deux? Leopold and Loeb remain murder’s cool/cruel uncles.

After all the books, plays, and films, how does the real story in The Leopold and Loeb Files stack up for drama? Bluntly, read from cover to cover, the book is a slog. As I said, it’s a reference work, not a thriller. True true crime doesn’t follow a plot. As compiler Nina Barrett has said elsewhere, it’s more of a “whydunit” than a whodunit. But the “why” of their crime isn’t a satisfying one, and it’s buried beneath a pile of text.

Not to say the book doesn’t have its rewards. There are photos to please the olde Chicago vintage fetishists out there, and Barrett offers many interesting side-notes and summaries about the case and the titular files. Her introduction provides the story of the files’ provenance, starting with their rediscovery in June 1988 by a university assistant archivist in the depths of the Northwestern University Law School basement vault. Based on that, I would have liked to have seen more of Ms. Barrett’s words and less straight transcription.

The book beautifully shows how little justice in America has changed. The two were non-minors, but were constantly referred to as “boys” by the defense, likely to portray them as a pair of callow knuckleheads who let things get out of hand. Sounds familiar.

Keep track of your glasses

Civil liberties hero Darrow does not come off well, though his eloquence during his closing statements remains impressive, if a bit puffy. Darrow invoked affluenza long before it had a name, claiming pampering and accelerated education left the pair with no moral center. “It is just as often a great misfortune to be the child of the rich as it is to be the child of the poor,” he said, in all seriousness. Odd that money simultaneously ruined Leopold and Loeb and saved them from the noose. The defense also suggested both had their psyches twisted by former governesses, citing mental and sexual abuse. But as Bennett suggests, these accounts—which included painfully personal assessments of the governesses’ every alleged flaw—smack of misogyny and xenophobia. The effort placed in protecting upperclass white male twits endures. These days Leopold and Loeb might have done far less time before having the record of their single youthful homicidal indiscretion purged. Who knows? Perhaps Harvard Law School-bound Nathan might have had a Supreme Court judgeship in his future.

The Leopold and Loeb Files is not a bad book, but it is not an easy book to read. I don’t mean that in the sense of grisliness, though some may be upset by the details of the crime. No, it’s not easy to read because it is a reference work, consisting of facts and testimony, not storytelling. I made myself finish it, but I can’t say I’m the richer for it. As a historical document, it’s important, and if there are Leopold and Loeb completists out there, they will feast well. The casual reader, however, may wish to simply skim their Wikipedia entry and leave it at that. I fancy there’s a long-term essay in the finding, researching, and preparing of the original documents as suggested by the book’s introduction. I would have liked to have heard more of that and less of the lawyers’ sniping, the professional witnesses’ willingness to fudge and adjust their observations, and Leopold and Loeb’s endless self-deception and prevaricating.

In sum, The Leopold and Loeb Files is an impressive record of a criminal clusterfuck, Leopold and Loeb coming off less like Lex Luthor and Professor Moriarty and more like a pair of sociopathic Bertie Woosters. But we didn’t need a thick compilation of lightly edited transcripts to tell us that. However, it does pose an eternal question: why are the self-professed Übermenschen of the world too damn stupid to realize they’re morons?

The Leopold and Loeb Files, published by Agate Publishing of Evanston, is available for $35 online or from local booksellers.

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Dan Kelly

Dan Kelly has been a writer and editor for 30 years, contributing work to the Chicago Reader, Chicago Journal, The Baffler, Harvard Magazine, The University of Chicago Magazine, and others.