Joey Aiuppa

December 1, 1907 — February 22, 1997 — Chicago, Illinois, United States

Joseph John Aiuppa, known on the streets as 'Joey Doves' and 'Joey O'Brien', was an American mobster who rose from a Prohibition-era enforcer to the top boss of the Chicago Outfit. He controlled organized crime in Chicago from 1971 until 1986, when a landmark federal skimming case brought his criminal reign to an end and sent him to prison for the rest of his life.

Early Life in Chicago

Joseph John Aiuppa was born in 1907 in Chicago, Illinois, the son of Sicilian immigrants. He grew up in the city's rough Near West Side neighborhood known as 'the Patch,' an area that produced many future members of the Chicago Outfit. As a young man, Aiuppa fell in with local street gangs during the Prohibition era, an environment that brought him into contact with Al Capone's organization. He built a reputation as a tough, reliable operator, qualities that made him valuable to the Outfit's leadership as the organization consolidated its grip on Chicago's rackets. His nickname 'Joey Doves' reportedly stemmed from a hunting arrest in which he was caught with an illegal haul of mourning doves, an incident that became part of his colorful underworld legend. By the time he reached adulthood, Aiuppa had firmly attached himself to the Outfit's inner circle, working his way up through gambling, vice, and enforcement operations that would define his decades-long criminal career.

Rise Through the Outfit

Aiuppa steadily climbed the ranks of the Chicago Outfit over the following decades, earning trust through his effectiveness in managing illegal gambling operations, particularly in the suburb of Cicero, Illinois, long a stronghold of organized crime activity. As leaders such as Al Capone, Tony Accardo, and Sam Giancana came and went through imprisonment, exile, or retirement, Aiuppa proved himself a capable and disciplined operator who avoided the flashy public profile that had brought down some of his predecessors. By 1971, with the Outfit's leadership in transition, Aiuppa emerged as the organization's boss, a position of significant power within America's national crime syndicate. Under his leadership, the Chicago Outfit extended its reach into lucrative Las Vegas casino operations, orchestrating a sophisticated skimming scheme that siphoned untaxed cash from casino counting rooms before it was ever reported as revenue. This scheme, which funneled millions of dollars back to Mafia families across the country, became one of the largest organized crime financial operations ever uncovered by federal investigators.

Conviction and Final Years

Aiuppa's downfall came through the FBI's sweeping investigation into the Las Vegas skimming operation, which implicated top figures from the Chicago Outfit and other Mafia families across the country. In 1986, following a lengthy federal trial, Aiuppa was convicted for his role in orchestrating the skimming scheme that had drained casino profits for years. He was sentenced to 28 years in federal prison, a punishment that effectively ended his criminal career and marked a major victory for federal prosecutors targeting organized crime's grip on legal gambling. The case was later dramatized in popular culture, most notably informing elements of Martin Scorsese's 1995 film 'Casino.' Aiuppa spent his remaining years incarcerated, his health declining as he aged behind bars. He died on February 22, 1997, at the age of 89, while still serving his sentence. His conviction is remembered as a pivotal moment in the decline of the Chicago Outfit's national influence, symbolizing the success of coordinated federal efforts to dismantle organized crime's hold on the American gambling industry.