Chicago's Mob Bosses

Big Jim Colosimo: killed in his own cafe at 22nd and Wabash Avenue on May 11, 1920. Colosimo was then the top mob boss of Chicago. His death, believed ordered by underlings Al Capone and Johnny Torrio, made way fro Capone’s rise as Chicago’s number one mobster. The FBI believes Colosimo was set up for the murder by a friend and guard, Big Jim O’Leary. O’Leary is the son of the Mrs. O’Leary whose cow is believed to have knocked down a lantern that started the famous Chicago Fire many years before. Colosimo was waiting at his restaurant with O’Leary allegedly preparing for a business meeting. The unknown gunman stepped out of the cloakroom and gunned Colosimo down, sparing O’Leary.

Johnny Torrio (1920-25): Torrio helped kill his uncle, Jim Colosimo, placing him briefly in charge of Chicago’s growing rackets and underworld endeavors, while his compatriot in crime, Al Capone, steadily strengthened his own power base. Having helped set up his own uncle for assassination, Torrio got the message when he escaped death in a foiled assassination attempt on his own life in 1925. Torrio turned over the rackets to his partner, Al Capone.

Al Capone (1925-32): Although his tenure seems short, Capone has had a lasting impression on Chicago and on the image of the city’s organized crime element. Capone’s life is legendary, having turned quiet little Cicero into a mob haven and putting it on the road to a career in political corruption, and bloodying the streets of Downtown Chicago during the prohibition era in brazen gunbattles and mob hits.

Frank Nitti (1932-43): He ran Chicago longer than Capone, who put him in charge of Chicago when Capone was sentenced and jailed. In 1943, fearing the same fate as his boss, Nitti, facing a certain conviction after a federal indictment, takes his life in a suicide.

Paul “The Waiter” : Ricca

Tony “Joe Batters” Accardo (1943-55): the pair share control of the mob dividing Chicago in territories. 

Sam Giancana (1955-66): Giancana surfaces as the muscle and the day to day manager of the mob’s rackets, although Ricca and Accardo remain in the background. Giancana, who is linked to the JFK assassination, flees to Mexico in 1966 and returns to Chicago in 1975, only to be murdered in a mob-ordered hit at his own home. Suspects in the killing include Anthony “The Ant” Spilotro, among a handful of suspects.

Accardo(1966-86): Quiet and laid back, Accardo sharpens the Mob’s operations, trying to move them into “legitimate” business operations. (He dies in 1992 following a six year retirement.)

Joe Ferriola (1986-89): Expands mob operations into Cicero, resulting in the indictments of a dozen of his top lieutenants. Others, like Wayne Bock, flee to the safety of underlings like Johnny “Apes” Monteleone. Dies of natural causes. (See ties to Ed Vrdolyak.)

Sam Carlisi and John DiFronzo (1989-93): Sharing power again after Ferriola’s death, and trying to reorganize after several rounds of sweeping federal indictments and crackdowns that cripple the old organization. Both are jailed in 1993. (See Carlisi.)

Joseph Lombardo (1995-present): Upon his release from prison, Lombardo takes control of the mob but seeks to maintain a low-profile role, wearing “beachfront” and casual clothes to disguise his power, he shuffles around constantly denying his mob role. It is Lombardo who keeps the now divided Chicago Outfit factions in line, despite numerous indictments and convictions. Lombardo still controls Cicero, despite the jailing of several officials there.

John DiFronzo is named in 1997 as the new Chicago Outfit boss, although mob watchers and justice department officials contend that DiFronzo’s rise is only part of a scheme by Lombardo to take the heat off himself and maintain his low profile, but hands on management of the Chicago mob’s continuing operations.