Few names in organized crime evoke as much intrigue as The Chicago Outfit. While the Mafia in New York has been immortalized in movies like The Godfather and Goodfellas, the Outfit has always carried a distinct identity — less glamorous, more brutal, and in many ways more pragmatic. Where New York’s families fought for slices of the city, the Outfit simply took Chicago whole. Its leaders understood power differently: politics, unions, gambling, and eventually casinos in Las Vegas.
From its roots in the vice districts of the early 20th century to the St. Valentine’s Day Massacre, from its hand in Hollywood extortion to the bloody days of Tony Spilotro in Vegas, the Outfit’s story is woven into the fabric of American history. This is not just a chronicle of gangsters, but of a city that was both their playground and their fortress.
What follows is an in-depth exploration of over a century of the Chicago Outfit — the men who built it, the crimes that defined it, the victims who fell under its shadow, and the legacy it still holds today.
Chapter 1: The Roots of Organized Crime in Chicago
At the dawn of the 20th century, Chicago was a city in flux. Immigrants poured in from Europe, bringing with them traditions, languages, and, in some cases, new ways of making money outside the law. The Irish dominated politics and law enforcement, while Italian and Jewish communities formed their own enclaves. Out of poverty and discrimination, gangs became both protection and opportunity.
One of the earliest underworld figures was Big Jim Colosimo, a flashy Italian immigrant who built a fortune on prostitution. His “house of ill fame” empire flourished in the city’s Levee District, where corrupt police officers looked the other way. Colosimo was flamboyant — diamonds, cars, fine clothes — but he was also short-sighted. When Prohibition loomed, he resisted moving into bootlegging, dismissing it as too risky.
Enter Johnny Torrio, Colosimo’s lieutenant and strategist. Torrio saw Prohibition as a gold mine. He was calculating and patient, preferring alliances and business acumen over random violence. But Colosimo refused to adapt. In May 1920, Colosimo was shot dead in his own café. Most historians believe Torrio arranged it, possibly with assistance from a young protégé he had brought from Brooklyn: Al Capone.
Chapter 2: Torrio and Capone – The Rise of Bootlegging
Torrio inherited Colosimo’s operations and began building what would become the Chicago Outfit. His vision was simple: consolidate criminal activity under one umbrella, enforce peace when possible, and eliminate rivals when necessary. Bootlegging became the lifeblood of the organization.
Capone, still in his twenties, was Torrio’s enforcer and organizer. He quickly gained a reputation for both charm and ruthlessness. Torrio expanded into gambling and brothels, but alcohol was the key. He built a network of breweries, transport systems, and speakeasies. Politicians and police were bribed to ensure business ran smoothly.
Conflict was inevitable. Irish gangs, especially the North Side Gang led by Dean O’Banion, resisted Outfit dominance. In 1924, O’Banion was gunned down in his flower shop by Torrio’s men. Retaliation came swiftly: Torrio was ambushed outside his home and nearly killed. Shaken, he decided to retire to Italy, leaving the empire in Capone’s hands.
Chapter 3: Al Capone’s Reign of Terror
With Torrio gone, Capone became the undisputed boss. By the mid-1920s, he controlled an empire that generated an estimated $100 million annually (over a billion in today’s dollars). His reach extended from breweries to politicians, from Chicago to Cicero, where he relocated after Chicago’s mayor cracked down on vice.
Capone cultivated a Robin Hood image, donating to charities and opening soup kitchens during the Depression. Yet behind the public façade was extraordinary violence.
The bloodiest episode came on February 14, 1929. Capone’s men, dressed as police officers, lined up seven members of Bugs Moran’s North Side gang against a wall and executed them with Tommy guns. Moran himself escaped, but the St. Valentine’s Day Massacre shocked the nation and cemented Capone’s reputation as a ruthless crime lord.
Despite the violence, law enforcement struggled to pin murders on him. The FBI finally found a weak spot: taxes. In 1931, Capone was convicted of tax evasion and sentenced to 11 years. His imprisonment marked the end of an era, but the Outfit was far from finished.
Chapter 4: The Nitti Regime and Hollywood Connections
With Capone in prison, Frank “The Enforcer” Nitti rose to prominence. Nitti lacked Capone’s charisma but was equally ambitious. He focused heavily on extortion and labor racketeering.
One of Nitti’s boldest moves was infiltrating Hollywood. The Outfit controlled projectionist unions, and through strikes and threats, it extorted millions from movie studios. Major names like MGM, Paramount, and Warner Brothers paid to keep their films running smoothly in theaters.
But in 1943, Nitti faced federal indictment. Terrified of prison due to previous health issues, he walked into a rail yard and shot himself in the head. His death paved the way for others, but it did not weaken the Outfit.
Chapter 5: The Quiet Power of Tony Accardo
After Nitti’s death, leadership passed to Tony “Joe Batters” Accardo, one of the most important figures in Outfit history. Accardo had earned his nickname after bludgeoning enemies with a baseball bat during Capone’s days. But unlike his predecessors, Accardo preferred a low profile.
Under his rule, the Outfit expanded quietly and methodically. Illegal gambling flourished in the suburbs. Accardo cultivated relationships with politicians and law enforcement, ensuring minimal interference. He also began looking west — to Las Vegas.
Accardo’s philosophy was longevity. He once famously said, “We never kill good guys, only bad guys.” Whether or not that was true, Accardo avoided the flamboyance that had doomed Capone and Giancana. He ruled into old age, dying peacefully in 1992 — a rare fate for a mob boss.
Chapter 6: The Glamour and Fall of Sam Giancana
By the 1950s, the Outfit entered a more glamorous era under Sam “Mooney” Giancana. Giancana was ambitious, flashy, and well-connected. He expanded gambling operations and strengthened the Outfit’s grip on Las Vegas.
Giancana was also linked to national politics. He allegedly worked with the CIA on plots to assassinate Fidel Castro, offering mob expertise in exchange for leniency. Rumors also connected him to the Kennedys — particularly through his relationship with singer Phyllis McGuire and alleged affairs between JFK and women in Giancana’s circle.
Giancana’s reign was turbulent. His high profile drew intense FBI attention, and by the 1960s, he was ousted. In 1975, after returning from exile, he was shot seven times in the head while cooking in his Oak Park home. The message was clear: the Outfit tolerated no liabilities.
Chapter 7: Las Vegas and the Skim
Perhaps the most infamous chapter of Outfit history unfolded in Las Vegas. Beginning in the 1940s, the Outfit used Teamsters Union funds, directed by Jimmy Hoffa, to finance casino construction.
Once the casinos — including the Stardust, Tropicana, and Hacienda — were running, Outfit operatives ensured profits were “skimmed” before being reported. Millions in untaxed cash flowed back to Chicago annually. Couriers carried the money in suitcases, often on commercial flights.
The man overseeing much of the Outfit’s Vegas interests was Anthony “Tony the Ant” Spilotro, an enforcer known for his brutality. Spilotro created the “Hole in the Wall Gang,” a burglary crew notorious for smashing through walls to rob jewelry stores and pawnshops. His violent reputation eventually made him a liability.
In 1986, Spilotro and his brother Michael disappeared. Their bodies were later found buried in an Indiana cornfield, beaten to death in one of the most infamous mob killings of the era — dramatized in Casino by Joe Pesci’s character Nicky Santoro.
Chapter 8: The Decline – Law Enforcement Strikes Back
By the late 20th century, law enforcement had more tools to dismantle organized crime. The RICO Act allowed prosecutors to target entire organizations rather than individuals. Wiretaps, undercover operations, and witness protection programs weakened the Outfit.
In 1978, FBI raids and testimony from insiders began unraveling the Las Vegas skim. The Nevada Gaming Commission cracked down, and corporations eventually replaced mobsters in running casinos.
In Chicago, the Outfit continued loan sharking, gambling, and labor racketeering, but its power waned. By the 1990s, the old dominance had crumbled, though remnants still operated quietly.
Chapter 9: Operation Family Secrets
The most devastating blow to the Outfit came in the 2000s with Operation Family Secrets. The case began when Frank Calabrese Jr., son of a feared Outfit hitman, secretly cooperated with the FBI. Wearing a wire, he recorded his father confessing to murders.
The investigation uncovered decades of crimes, including 18 murders committed between 1960 and 1986. The trial, held in 2007, featured chilling testimonies about mob hits, extortion, and corruption.
Top Outfit figures, including Joseph Lombardo, James Marcello, and Frank Calabrese Sr., were convicted. It was one of the most significant organized crime trials in U.S. history, finally pulling back the curtain on the Outfit’s darkest secrets.
Chapter 10: The Outfit Today
While the Outfit has been severely weakened, it has not disappeared. Modern reports suggest it still operates in Chicago and its suburbs, focusing on illegal sports betting, video poker, loan sharking, and union corruption.
Unlike the flashy bosses of old, today’s Outfit leaders stay in the shadows, avoiding the public eye and keeping operations quiet. They no longer dominate Chicago politics or the national stage, but their survival into the 21st century proves the adaptability of organized crime.
Conclusion
The Chicago Outfit’s story is one of power, violence, and resilience. From the Prohibition bootlegging wars to the glitter of Las Vegas, from Capone’s reign to the Family Secrets trial, it has left a mark on American culture unlike any other crime syndicate.
Its history reflects more than just crime — it reflects America’s contradictions: prosperity and corruption, opportunity and exploitation, freedom and lawlessness. The Outfit may no longer wield the iron grip it once had, but its legend remains, forever entwined with the city of Chicago.
