Corruption, Killings, and Courtrooms: A Chicago True Crime Reading List

My hometown, Chicago, is a city that rewards attention. I decided to become a criminal trial lawyer at the age of ten, when The Defenders, a television show about a father-son criminal defense team in New York was broadcast on CBS. Only I became a criminal prosecutor rather than a defense attorney. I spent years in Chicago’s criminal courts as an Assistant Cook County State’s Attorney, which I chronicle in my new book, Felony Review: Tales of True Crime and Corruption in Chicago.

One thing that never left me is how thoroughly crime and justice are braided into the city’s identity: organized crime and reform, political power and civic idealism, corruption and genuine courage. You can’t really read Chicago crime without reading Chicago itself.

Here is a list of true crime books that capture the city I recognize: its institutions, its appetites, its betrayals, and the strange moral clarity that sometimes appears in the middle of a messy case. In Chicago, the truth is stranger and more interesting than fiction.

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Erik Larson, The Devil in the White City

The 1893 World’s Fair was a monument to civic ambition—and, in the shadows, there was a serial killer named H. H. Holmes. Larson captures Gilded-Age Chicago as it modernized at high speed: dazzling architecture, big money, and the loose seams that can let skillful predators thrive undetected. Read it for the period as much as the crimes.

Adam Selzer, H. H. Holmes: The True History of the White City Devil

If Larson gives you the spell, Selzer gives you the file. He digs into what the record actually supports, separates documented fact from legend, and shows how Chicago turns stories into mythology. A bracing companion for readers who want the history as well as the atmosphere.

Kenneth Tucker, Eliot Ness and the Untouchables: The Historical Reality and the Film and Television Depictions (Second Edition)

Eliot Ness exists in two forms at once: the historical lawman and the cultural icon—burnished by the old TV series I watched as a kid and by the later film I did not enjoy nearly as much. As I write this, I am looking at an autographed picture of Robert Stack as Eliot Ness in his three-piece suit on the wall of my home office. Tucker takes both lawman and icon seriously, tracing the real Ness while also explaining how Chicago’s Prohibition-era story was retold, reshaped, and sometimes romanticized by Hollywood.

A family footnote: when my grandmother was a little girl, she once met Ness when he came into her father’s store to buy candy—a small moment, but one that always made him feel less like a legend and more like a real person who walked the streets of my town.

Terrence Hake (with Wayne Klatt), Operation Greylord: The True Story of an Untrained Undercover Agent and America’s Biggest Corruption Bust

Full disclosure: Terry Hake and I were sworn in as Cook County prosecutors on the same day, and he figures prominently in Felony Review. (I make a brief appearance in his book as well.) With a subtitle that aptly summarizes the story, Operation Greylord is essential reading because it shows how wholesale corruption actually worked in “Crook County.”

It’s also a rare inside look at how a major corruption investigation gets built from the ground up, and how it led a disillusioned young lawyer to put it all on the line.

Robert Cooley (with Hillel Levin), When Corruption Was King: How I Helped the Mob Rule Chicago, Then Brought the Outfit Down

Another disclosure: I knew Robert Cooley from my days in misdemeanor branch courts, when I was a prosecutor and he was a “fixer” defense lawyer, and his ASA brother Dennis was my supervisor in auto-theft court. Both brothers make an appearance in Felony Review. Robert Cooley’s story is classic Chicago: the world of “fixing,” the proximity of money and muscle, and the way a city can talk itself into tolerating the intolerable.

Jonathan Dixon, Gregg Owen, Convergence

I knew of Gregg Owen from my days as an ASA (not personally or closely), when our tenures overlapped. Before law school, he was the keyboard player for Chicago rock band, and he looked the part. What makes his book Convergence unusual—and worth a place on a Chicago list—is its angle: it focuses on a single serious case and tells the story from the prosecution side of the courtroom.

You will learn in detail how a case is built, preserved, and tried, especially when forces outside the courtroom try to keep it from ever reaching a jury. It’s a prosecutor-positive true crime book, which is rarer than it should be.

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