You’ve probably seen the movies. In the 1987 film The Untouchables, Frank Nitti is a white-suited, sociopathic hitman who gets tossed off a roof by Eliot Ness. It’s a great scene. Cinematic, satisfying, and completely fake.
The real Frank Nitti, the man they called "The Enforcer," was arguably more interesting than the Hollywood version, though far less of a street brawler. He wasn't a muscle-bound thug. He was a 5-foot-6-inch barber-turned-accountant who preferred expensive silk ties to tommy guns.
Honestly, the nickname itself was kind of a joke.
In the inner circles of the Chicago Outfit, Nitti was known for being a meticulous stickler for the rules. He made sure the booze shipments arrived on time and the books balanced. He "enforced" the organization's schedule and logistics. But when the media got wind of the name, they painted him as a bloodthirsty executioner. Nitti, being a savvy businessman, didn't exactly go out of his way to correct them. Fear is good for business, after all.
From Barbering to the Big Time
Born Francesco Raffaele Nitto in 1886—or maybe 1881, depending on which record you trust—he grew up in the same Brooklyn neighborhood as Al Capone. They weren't cousins, despite what old-timey journalists loved to claim. But they were close. While Capone was out making a name for himself with his fists, Nitti was cutting hair and learning how to fence stolen jewelry.
He moved to Chicago around 1913. He wasn't some high-ranking mafioso yet. He was just a guy with a barber chair and a talent for networking. He met guys like Dean O'Banion and Alex Louis Greenberg, eventually getting into the lucrative world of liquor smuggling.
When Prohibition hit, the world changed.
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Nitti’s value wasn't in how well he could shoot; it was in how well he could organize. Al Capone realized this early on. While Capone was the face of the Outfit—the loud, charismatic, violent "Big Fellow"—Nitti was the engine room. He managed the day-to-day distribution of Canadian whiskey through a massive network of speakeasies.
If Capone was the CEO, Nitti was the COO. He was the one who kept the trucks moving and the cops paid.
The Shooting at LaSalle Street
Most people think the law eventually "got" Nitti, but they nearly killed him first. In December 1932, a team of Chicago police officers raided Nitti’s office. It wasn't a standard arrest. Detective Sergeant Harry Lang shot Nitti three times at point-blank range—in the back and neck.
Then, Lang shot himself in the arm.
He wanted to make it look like a shootout. Why? Because the newly elected Mayor, Anton Cermak, reportedly wanted the Outfit dismantled and replaced with gangsters he could control. Lang had allegedly been paid $15,000 to execute Nitti on the spot.
Nitti survived.
He didn't just survive; he beat the rap. During the trial, another officer testified that Nitti was unarmed when he was shot. Nitti was acquitted of attempted murder, and the crooked cops were the ones who ended up in trouble. This incident cemented Nitti’s reputation as a man who could "beat the heat," but it also left him with a lifelong physical and mental frailty.
Taking the Reins (Sorta)
When Capone went to prison for tax evasion in 1931, someone had to step up. Nitti is often listed as the "Boss" who succeeded him, but the reality is more nuanced.
The Chicago Outfit was moving toward a board-of-directors style of leadership. Nitti was the front boss—the guy the public and the FBI looked at. But behind the scenes, men like Paul "The Waiter" Ricca and Tony Accardo were starting to hold the real power.
Under Nitti’s watch, the Outfit moved away from the "messy" violence of the Prohibition era and toward more sophisticated labor racketeering. Their biggest target? Hollywood.
The Great Hollywood Shakedown
This was Nitti's masterpiece and his undoing. Working with union thugs like Willie Bioff and George Browne, the Outfit took control of the stagehands' union (IATSE).
They didn't just ask for a cut of the profits. They threatened to shut down every movie theater in America.
Studio moguls at Paramount, MGM, and 20th Century Fox were terrified. They paid millions in "protection money" just to keep the film reels spinning. Nitti famously said, "The goose is in the oven just waiting to be cooked." For a while, the money was better than it had ever been during the bootlegging days.
The End of the Enforcer
The Hollywood scheme eventually collapsed when Willie Bioff turned informant. In March 1943, a federal grand jury indicted the top tier of the Chicago Outfit.
The "board of directors" met at Nitti’s home. It was a tense, ugly meeting. Paul Ricca didn't mince words: since the Hollywood plan was Nitti’s baby, Nitti should be the one to go to prison and take the fall for everyone.
This was a death sentence for Frank.
Nitti suffered from severe claustrophobia. His previous 18-month stint in prison had nearly broken him. The thought of spending 10 or 20 years in a cramped cell was more than he could handle. There were also rumors that he was dealing with terminal cancer, though that’s never been fully proven.
On March 19, 1943, after his wife left for church, Nitti started drinking. Heavily.
He walked down to the Illinois Central railroad tracks in North Riverside. A freight train crew saw him staggering along the tracks. They thought he was a drunk. They shouted at him to get out of the way.
Nitti stepped off the tracks, leaned against a fence, and pulled out a .32 caliber revolver.
It took three shots. The first two went through his hat. The third was final.
Why Nitti Still Matters
The death of Frank Nitti marked the end of the Capone era. He was the bridge between the wild, street-warfare days of the 20s and the corporate, "quiet" Mafia of the mid-20th century. He proved that you didn't need to be the strongest guy in the room to run the city; you just needed to be the one who understood the ledger.
What we can learn from Nitti's story:
- The Power of Branding: His "Enforcer" nickname shows how a public image can be totally disconnected from reality.
- The Risk of the "Front": Being the face of an organization means you’re the first one the law—and your "partners"—will sacrifice.
- Adaptation: Nitti’s move from bootlegging to labor unions is a textbook case in how criminal (and legitimate) enterprises must pivot to survive changing laws.
If you’re researching the history of the Chicago Outfit, don't stop at Capone. Nitti was the one who actually made the machine work. Dig into the trial transcripts of the 1943 Hollywood Extortion case to see just how deep his influence reached into the entertainment world we know today.
Next Steps:
Research the 1943 Hollywood Extortion Trial to see how the Outfit’s influence shaped the modern film industry's labor unions. You can also look into the life of Paul Ricca, the man who truly took over after Nitti and changed the Mafia into a global shadow corporation.