THE BOSSES

1915–1920
JIM COLOSIMO
Old-time pimp and barkeep

1920
Prohibition sparks a Mob bootlegging bonanza

1920–1925
JOHNNY TORRIO
New-world Mafioso who brings NYC-style ruthlessness and organization to Chicago

1925–1932
AL CAPONE
Defeats rival gangs, but brought down by the IRS and syphilis

1929
St. Valentine’s Day Massacre solidifies Outfit dominance

1932–1939
FRANK NITTI
Known for union extortion; commits suicide in 1943

1939-1944
PAUL RICCA
Pushes Nitti aside; goes to prison for extortion

1943
Several bosses indicted for Hollywood union extortion

1944–1957
TONY ACCARDO
Brings the Outfit to its greatest power, imposing a street tax and building Las Vegas

1951–1957
Senate probes force the FBI to investigate the Outfit

1957–1965
SAM GIANCANA
Flashy “CEO” chosen by Accardo, who remains “chairman”

1960
The Outfit takes control of Las Vegas’s biggest casino group

1975
Giancana hit after he is called to testify before the Senate

1965–1992
TONY ACCARDO
After booting Giancana, Accardo stays in charge as the Mob begins to decline

1982
A Teamsters pension exec, convicted for Mob links, is killed

1986
Operation Strawman targets the Outfit’s casino-skimming operation

1989
Operation Gambat which exposes Mob ties to courts and politicians

1992–1997
SAM CARLISI
Weak leader during a time when other bosses are sick or in prison

2007
Family Secrets trial convicts five Outfit members for 18 murders

1997–present
JOHN DiFRONZO
Slick and cautious; focused on gambling

SOURCE: THE CHICAGO CRIME COMMISSION
 

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Photography: (Colosimo, Torrio, Nitti, Giancana) Bettmann/Corbis/AP; (Capone, Accardo) AP; (Carlisi) Courtesy of the U.S. Attorney’s Office; (DiFronzo) Carl Wagner/Chicago Tribune