Joseph Aiuppa, known by aliases such as Joey O’Brien and Joey Doves, rose to become the boss of the Chicago Outfit in 1971 and held that position until his conviction for casino skimming in 1986. Born in Melrose Park, Illinois, Aiuppa was the eldest son of Sicilian immigrants from Lascari, Sicily. A former boxer, he began his criminal career as a driver for high-ranking Outfit members, including Tony Accardo, before moving up the ranks during the Prohibition era. By the early 1930s, Aiuppa was running gambling operations in Cicero, Illinois, including bookmaking rings and underground casinos hidden behind secret entrances.
He also managed Taylor and Company, a business that appeared to manufacture furniture but actually produced illegal slot machines. His influence extended into labor racketeering as a founding member of Local 450, a union for hotel and restaurant employees tied to the Capone mob. Law enforcement identified Aiuppa in 1935 as a skilled marksman and expert bank robber linked to notorious criminals such as John Dillinger and Claude Maddox. His reputation for ruthlessness helped cement his standing in Chicago’s underworld.
From the late 1940s through the 1960s, Aiuppa became the power behind the Cicero District, historically the Outfit’s economic stronghold since Al Capone’s reign. Under his control, Cicero remained the organization’s most profitable territory. He managed several establishments along the area known as “the Strip,” which was a precursor to the mob-run Las Vegas casino strip. Operations centered on Cermak Road in Cicero, with clubs such as the Frolics, the Town Hotel, and the 411 Club serving as hubs for gambling, prostitution, and slot machines.
Aiuppa also invested in real estate through Rosar Realty, a company named for his mother, Rose Marie. Properties were often registered under relatives such as brothers and nephews to obscure his true wealth. He later sold the Navajo Hills Golf Course in suburban Chicago, and he retained ownership of his residence in Oakbrook, Illinois. Aiuppa carried the nickname Joey O’Brien from his boxing days.
At the time, Irish boxers were favored and earned more money, so Aiuppa adopted the Irish-sounding alias to secure better fights. The name was later shortened in mob circles to O’Brien or Joey O. In a case reminiscent of Al Capone’s tax evasion conviction, Aiuppa was prosecuted in 1966 not for mob activity, but for the illegal possession and transportation of mourning doves across state lines, violating the Migratory Bird Treaty Act of 1918. The act prohibits possessing more than 24 doves per person outside hunting season.
The charge stemmed from a 1962 FBI search of Aiuppa’s car in Kansas, during which agents discovered 563 frozen doves. The investigation was part of Robert F. Kennedy’s broader crackdown on organized crime in Chicago. Aiuppa was sentenced in 1966 to three months in jail and fined $1,000.
The unusual nature of the conviction earned him nicknames including Joey Doves, Joey the Doves, Doves, and Morning Doves, a defining part of his legacy that blended his mob ties with a moment of ironic legal downfall. After Sam Giancana’s death, Aiuppa rose to prominence within the Chicago Outfit in 1971, following the imprisonment of Felix “Milwaukee Phil” Alderisio. Aiuppa officially took over as boss, a leadership era marked by strengthened connections to Las Vegas casino operations and expanded influence. His dominance faced a setback with his indictment and imprisonment in the mid-1980s, leading to a transitional period in which Joseph Ferriola assumed control from 1985 to 1988.
Samuel Carlisi, Aiuppa’s trusted chauffeur and protégé, later stepped into the leadership role. Following Giancana’s death, Aiuppa acquired a residence in Palm Springs, California, following a pattern among high-ranking mob figures who retreated to more discreet settings while continuing to exert influence. In 1986, Aiuppa was convicted of skimming millions in profits from Las Vegas casinos and sentenced to 28 years in prison. The conviction stemmed from testimony, including that of Joseph Agosto of the Kansas City crime family, who exposed a scheme siphoning $2 million from casino revenues.
Also implicated and imprisoned alongside Aiuppa were Carl DeLuna, Angelo J. LaPietra, and Jackie Cerone. LaPietra, known as “the Hook,” had long been a top enforcer for Aiuppa with deep roots in Cicero’s criminal operations. From prison, Aiuppa maneuvered to maintain the Outfit’s power, entrusting John “No Nose” DiFronzo to oversee operations in Chicago’s western suburbs, bypassing acting boss Joseph Ferriola.
In June 1986, tensions escalated with the brutal murders of Anthony “Tony the Ant” Spilotro, a notorious enforcer, and his brother Michael. Their beaten bodies were discovered buried in a cornfield in Enos, Indiana, just five miles from Aiuppa’s property near Morocco, Indiana. Testimony from Nicholas Calabrese, the first made man to turn state’s witness against the Outfit, revealed that the brothers were killed in a home in Bensenville, Illinois, before their bodies were disposed of in Indiana. Nicholas’s nephew, Frank Calabrese Jr.
, also became an informant, aiding FBI investigations. Conflicting narratives linger. In a 2010 interview, Tony Spilotro’s son Vincent claimed his uncle Michael was the primary target, with Tony’s murder meant to preempt retaliation. Aiuppa served nearly 10 years of his sentence before being released on January 19, 1996, from the Federal Medical Center in Rochester, Minnesota.
On February 22, 1997, he died at Elmhurst Memorial Hospital in Elmhurst, Illinois. He was buried at Queen of Heaven Cemetery in Hillside, Illinois. Aiuppa’s legacy is tied to the mafia’s control of Las Vegas through skimming operations, which ensured a steady flow of untaxed money to the Outfit. His involvement was pivotal to the organization’s financial success but also drew significant law enforcement attention.
Many believe Aiuppa ordered the 1986 murders of the Spilotro brothers, who were Outfit members that had fallen out of favor, further cementing his reputation as a ruthless enforcer of mafia discipline. Aiuppa helped modernize the Chicago Outfit, making it a significant player in national and international organized crime. However, his tenure also marked the beginning of the Outfit’s decline, as increased law enforcement scrutiny and internal betrayals weakened its grip.
He is remembered as a quintessential mafia boss—calculating, ruthless, and business-savvy—whose leadership style left a lasting imprint on organized crime in America.