Frank Nitti: The Enforcer Who Took Over The Chicago Outfit

04 May, 2025

Was Frank Nitti, the man who took the reins of the Chicago Outfit after Al Capone, a ruthless killer or a shrewd strategist? The truth, as with many figures of the Prohibition era, is far more complex, painting a portrait of a man who balanced violence with an almost paradoxical aversion to getting his hands dirty, ultimately shaping the landscape of organized crime in America.

Frank Nitti, born Francesco Raffaele Nitto in Sicily in the 1880s, arrived in America with the promise of a new life. Little did the young immigrant know he would become a key player in one of the most notorious criminal organizations in American history. Beginning his career in the underworld as a barber and fence for stolen goods, Nitti swiftly climbed the ranks of the Chicago Outfit, eventually becoming Al Capone's right-hand man, a role that earned him the chilling moniker, "The Enforcer."

Nitti's rise within the Outfit was marked by a calculated ruthlessness. He orchestrated numerous violent acts for Capone, yet possessed a remarkable ability to stay out of direct involvement, keeping his fingerprints off the weapons and maintaining a distance that would prove crucial later on. This ability, combined with his sharp financial acumen, made him a valuable asset to the gang.

Attribute	Details
Full Name	Francesco Raffaele Nitto (also known as Frank Ralph Nitto)
Born	Sicily, Italy, sometime in the 1880s (Sources vary, with some citing 1883 or 1886)
Died	March 19, 1943, Chicago, Illinois (Suicide)
Known For	Chief enforcer of Al Capone and later, the boss of the Chicago Outfit.
Nickname	"The Enforcer"
Criminal Activities	Bootlegging, extortion, racketeering, murder.
Marriage	Annette Caravetta (married May 14, 1942)
Career Path	Barber, fence for stolen goods, member of the Chicago Outfit, eventually becoming boss.
Imprisonment	Served 18 months for tax evasion (1931)
Notable Relationships	Al Capone, Edward J. O'Hare (Secretary to a race track operator), Annette Caravetta (wife).
Controversies	Death by suicide to avoid extortion trial, suspected involvement in the murder of Edward J. O'Hare.
Associated Locations	Chicago, Illinois (primarily), New York (early residence).
Reference Website	Britannica - Frank Nitti

In 1931, the law finally caught up with Capone and Nitti, with both being convicted of tax evasion. While Capone received a lengthy prison sentence of eleven years, Nitti's sentence was considerably lighter, only eighteen months. Even this brief incarceration proved challenging for the man often described as claustrophobic.

Upon his release from prison in 1932, Nitti was immediately hailed by the press as the new boss of the Outfit. The transition, however, was not seamless. The existing power structure had to be maintained. Nitti, despite his relatively short time behind bars, had already cemented his position as the one in charge.

Nitti's leadership style was characterized as quiet and calculated. He preferred to work behind the scenes, using his influence to control the monetary matters of the Outfit. This approach allowed him to avoid the spotlight and continue to operate, navigating the treacherous waters of the criminal underworld with a keen understanding of power dynamics and the importance of strategic alliances. He was a master of the long game, always planning for the future of the organization.

The details of Nitti's personal life are shrouded in the same mystery and intrigue as his professional one. He lived with his wife, Annette, in an apartment in Chicago. His marriage to Annette Caravetta on May 14, 1942, just a year before his death, added another layer to the complexities of his life.

The year 1943 marked a turning point. On December 19, 1932, Nitti was seriously wounded. This incident didn't stop him from running the Outfit but put him on the map for rival gangs. The world then observed Nitti's career coming to an end.

The pressure mounted in the face of a looming trial on extortion charges. Rather than face the legal consequences, Nitti chose to take his own life on March 19, 1943, ending his reign as the boss of the Chicago Outfit. His death, shrouded in mystery, left a void in the organization.

Even in death, the legacy of Frank Nitti continues to fascinate. The question of whether he was a respected leader or a ruthless killer still lingers. His story is a reminder of the brutal realities of organized crime and the complex characters who shaped its history. The very walls of 33 West Kinzie, the former home of Harry Carays Italian Steakhouse, have been said to be haunted by the ghost of the enforcer, an eternal reminder of the man who rose from the streets of Chicago to lead one of its most notorious gangs.

The location of the Harry Caray's Italian Steakhouse at 33 W Kinzie, became synonymous with Nitti, with many people and staff members claiming to see his ghost there. This location added another layer to the allure of Nitti and his continued influence over the city.

The legacy of Frank Nitti remains an enigma. Some admire him as a capable leader who skillfully managed the Outfit's affairs, while others view him as a remorseless killer. His story reflects the brutal reality of organized crime and the intricate characters who shaped its history. His death still remains controversial.

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Frank Nitti by HenriqueMart on DeviantArt

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