The Chicago Outfit is that city’s branch of the American Mafia. Its modern organization dates to the beer
wars of Prohibition and its most notorious leader, Al Capone. It has a seat, along with the Five Families of New York City, on the Commission that governs the Italian mob in America.
The Outfit’s roots reach back to the early 1900s and an influx of Italian immigrants to Chicago. Street gangs, some of them Italian in background, controlled various criminal activities in the city.
At the same time, extortionists practiced the “Black Hand” scheme imported from Italy. This involved threatening residents with violence unless money was paid. Extortion letters were stamped with a hand in ink, hence the name. Many Black Hands worked independently, but some joined forces, forming organized criminal syndicates.
But the Chicago Outfit truly came into its own in the 1920s. Giacomo “Big Jim” Colosimo, who ran hundreds of brothels, had solidified power over large portions of the underworld during the Black Hand era. He welcomed his nephew, Giovanni “Papa Johnny” Torrio, to the scene, and in 1919 Torrio introduced a new face: Alphonse “Scarface” Capone.
Prohibition took effect in 1919, but Chicago, like other cities, simply sent its liquor underground. Torrio urged his boss to go into the booze business, but Colosimo refused. To remove this impediment, Torrio had Colosimo killed. What followed were the “beer wars,” the most violent episode of organized crime in American history.
Before Prohibition, the Outfit had focused on gambling and prostitution. Now that bootlegging had joined the repertoire, frequent bouts of murder followed. Torrio’s gang controlled the South Side and the Loop but soon began to expand into the Gold Coast, where Dean O’Banion and the Irish-American North Side Gang ruled.
For a while the two sides managed a truce, but it didn’t last long. O’Banion scammed Torrio out of half a million dollars, and Torrio retaliated. On November 10, 1924, O’Banion was murdered in his flower shop. His death resulted in all-out urban warfare.
Tommy-gunfire raged back and forth. The North Siders tried to kill Torrio but failed. The experience jarred him, and he retired. He handed the reins of the Outfit to Capone, whose fortunes soared.
Then, in 1929, after five years of gunfire between the North and South sides, Capone made a move intended to cripple his enemies. It had the opposite effect. On February 14, he sent a group of men to a garage on North
Clark Street, where they unloaded their guns into seven members of the North Side Gang. The “St. Valentine’s Day Massacre” drew so much negative publicity the city was forced to crack down on organized crime.
The federal government joined the effort, prosecuting Capone for tax evasion. He went to prison, and his criminal enterprise suffered without him, but it didn’t die. In fact, it soon bounced back and began to spread its wings.
After Capone left in 1932, control of the Outfit passed to Frank “The Enforcer” Nitti, a former bodyguard who had risen to become a leader of the organization’s bootlegging operations. But the real decisions were made by his underboss, Paul “The Waiter” Ricca.
When Prohibition ended in 1933, the Outfit was forced to focus on other criminal enterprises, such as prostitution, labor racketeering and especially gambling. Under Nitti and Ricca, it also began to expand. The organization set up shop in Wisconsin, Missouri, Los Angeles and Las Vegas, where it eventually took over control of legal casinos from the Five Families.
These expansion tactics led to a major scandal and a raft of indictments in 1943, when the FBI caught Chicago gangsters shaking down the movie industry in Hollywood. Nitti was set to take the blame, but he had served time before, was severely claustrophobic, and decided he couldn’t handle prison again. Instead he shot himself in the head while wandering a Chicago rail yard.
Ricca formally became boss and appointed Tony “Joe Batters” Accardo his lieutenant. Together they ran the Outfit for the next 30 years, though their titles and roles changed. After Ricca’s death in 1972, Accardo led the Outfit for another 20 years. Accardo is considered one of the smartest bosses of the American Mafia: Over a criminal career that spanned 70 years, he spent only one night behind bars.
The Outfit grew to encompass most mob operations in the Western United States during the Ricca-Accardo years. It reached its peak during the 1960s, when Accardo’s flashy front man, Sam “Momo” Giancana, attempted to orchestrate the assassination of Fidel Castro for the CIA and briefly had an affair with a woman who was also sleeping with President John F. Kennedy. Giancana was kicked out of the Outfit in 1966 and murdered in 1975.
His job as titular head of the Outfit was filled by Joey “Doves” Aiuppa, who held that position until his conviction in 1986 for skimming profits from Las Vegas casinos. Though he spent 11 years in prison, he had his revenge: He allegedly ordered one of the most famous hits in Mafia history, the murders of Michael and Tony “The Ant” Spilotro, who were beaten, strangled and buried in an Indiana cornfield in retaliation for the mismanagement of the casinos. These killings, and the Las Vegas history that led to them, were depicted in the movie Casino.
After Aiuppa went to prison, control of the Outfit was handed to several other mobsters, while James “Little Jimmy” Marcello acted as front man. In the years to follow, the organization began to lose much of its power in Chicago and the Western United States. Las Vegas went legitimate, labor unions began to purge themselves of gangsters, and federal trials sent large numbers of Mafiosi to prison for long terms.
The Outfit was dealt perhaps its most crushing blow in 2007. The FBI managed to flip several high-ranking members in an operation dubbed ” Family Secrets,” one of the most successful federal investigations of organized crime. The resulting trial ended with the conviction of five men on charges of conspiracy and racketeering for crimes that included several murders. Another six pleaded guilty, two died before trial and a ninth was too ill to face prosecution. Marcello was convicted in part for the murder of the Spilotro brothers. The Outfit has dwindled in recent years, but it isn’t dead. As the Family Secrets investigation demonstrated, racketeering is still at the heart of its operations. It doesn’t have the reach it once did, but it remains a major part of the world of crime in Chicago.