WTTW Explores the "Crime of the Century" in a New Documentary on Leopold and Loeb, a Century Later

Chicago Stories: Deadly Alliance – Leopold and Loeb premieres Friday, September 20 at 8:00 pm on WTTW and at wttw.com/chicagostories or the PBS app. Explore the companion website now. 

On Friday, September 20 at 8:00 pm, an all-new season of WTTW’s Chicago Stories kicks off with a look back at one of the most sinister true crime stories of the 20th century, which took place in Chicago 100 years ago. We asked the film’s producer and writer Tania Lindsay to share what it was like to tell the story of Leopold and Loeb and why this “Crime of the Century” is still so compelling.

This interview has been condensed and edited for clarity.

What makes this story so intriguing?

The story of Nathan Leopold and Richard Loeb captivated the nation – and the world – with the shocking depravity of its wealthy, good-looking, and intelligent perpetrators. Leopold and Loeb were two young Chicagoans who, in May 1924, embarked on a plan to commit the perfect crime and prove their intellectual superiority by plotting the abduction and murder of a 14-year-old boy named Bobby Franks. Their motive was a disturbing desire for thrills and the misguided belief that they could get away with it.

What was it about the murder that immediately captivated the public?

The sheer audacity and coldblooded ruthlessness of the murder have kept this story a subject of intrigue and fascination for 100 years. The same elements were there from the start – an innocent young boy walking home from school was snatched away from his loving, wealthy family and murdered for no apparent reason. From the first clues – a pair of eyeglasses dropped at the scene and a typewritten ransom note – to the psychological profiles of the killers, every minute detail of the case was laid bare for public consumption.

Why were people so surprised to discover that Leopold and Loeb had committed this crime?

They were teenagers, just 18 and 19 years old; University of Chicago students who were often called “geniuses” and excelled at their wholesome hobbies – birding and tennis. They were supposed to be among the next generation of thought and business leaders in Chicago. Instead, they threw it all away for the thrill of taking a boy’s life. I think most people have a hard time understanding how two such accomplished people could make that choice.

Leopold and Loeb instantly became infamous after they confessed. What was the media frenzy like before and during their sentencing hearing?

From the moment Bobby Franks’ body was found, six Chicago daily newspapers seized upon the shocking nature of the crime, publishing sensational headlines and articles. The press was embedded in every aspect of the case, and the competition for stories was so fierce that reporters would do anything and everything to get a scoop, including paying police for tips and access. Every detail they could find was printed, including many that were factually incorrect or overblown. Some of that misinformation still exists in the popular understanding of this story.

The legendary attorney Clarence Darrow got involved in this case. What was his impact on the outcome?

Leopold and Loeb were surely headed for the hangman’s noose, and most of the country would have considered that fair justice. Clarence Darrow’s masterful two-day oral argument at the sentencing hearing, which challenged the concept of capital punishment, reportedly brought many in the courtroom to tears. Darrow said, “I am pleading that we overcome cruelty with kindness and hatred with love.” In the end, Darrow persuaded the judge to show mercy, and Leopold and Loeb were sentenced to life plus 99 years. So he singlehandedly saved their lives.

Did you film in any of the actual locations where the events took place?

Yes, there are a number of relevant Chicago-area locations that still exist today, including the University of Chicago campus, much of which would have looked very similar to Leopold and Loeb. We were able to rent a vintage Willys-Knight automobile similar to the one used by Leopold and Loeb to pick up Bobby Franks near his private school, the Harvard School for Boys, now an apartment building. We filmed near there, and also near the Franks’ stately Kenwood mansion, which has been beautifully restored and now contains luxury condos.

What does this documentary reveal about Leopold and Loeb that might be new to viewers?

After decades of interest in this story, it was hard to imagine uncovering anything new. But in 2022, Richard Loeb’s nephew revealed a trove of new archival materials that were found among his mother’s possessions after her death. We were able to use never-before-seen photos, letters, and other documents related to Richard Loeb that had been donated to Northwestern University’s archives.

Why does a 100-year-old murder still resonate today?        

This story has an intoxicating mix of youth, wealth, mystery, and courtroom drama. On top of that, underlying themes of homosexuality, elitism, and the psychology of criminality provide endless areas to explore for deeper meaning.

What do you hope viewers will take away from this documentary?

I hope viewers will be excited to explore the mystery, intrigue, and psychological drama of this 1924 true crime story. At the same time, Bobby Franks, the 14-year-old victim, has been lost to history while Leopold and Loeb remain well known. I hope viewers will feel sympathy for the Franks family and understand that, as thrilling as true crime stories can be, there is always a human cost.