In September 1960, Momo Salvatore Giancana, a successor of Al Capone's in the Chicago Outfit, and Miami Syndicate leader Santo Trafficante, who were both on the FBI's Ten Most Wanted list at that time, were indirectly contacted by the CIA about the possibility of Fidel Castro assassination.
As part of the arrangement, the Chicago Outfit's enforcer, Anthony Spilotro (under the name of Tony Stuart) was granted a gift shop concession in the hotel.
Horan, however, initially attempted to avoid being put under the influence of Capone and his Chicago Outfit.
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Under Horan's presidency, the union's ties to the Chicago Outfit deepened.
Some people claim that gangsters referred to as the Chicago Outfit associated with Al Capone would take the train from Chicago and stay at the hotel.
Pia Rizza is the daughter of Vincent Rizza, who worked for the The Chicago Outfit, then subsequently testified against them and entered the Federal Witness Protection Program.
Dovi had good connections with the Chicago Outfit and the five families of New York, and expanded operations to Atlantic City, South Philadelphia and parts of South Jersey.
The hotel became known for a murder in 1983, when Teamsters lawyer and alleged Chicago Outfit mobster Allen Dorfman was shot in its parking lot.
Rudolph C. "Rudy" Fratto (born December 12, 1943) has been identified by federal authorities and several Chicago newspapers as a high-ranking member of the Chicago Outfit crime organization.
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He joined Sangerman's Bombers, a group of bomb terrorists which had emerged from the remnants of the James Sweeney gang, and did work for Al Capone's Chicago Outfit.
While on the stand, Calabrese stated that his association with the Chicago Outfit dated to May 1970, and that he began cooperating with the government in January 2002, after federal investigators confronted him with a bloody glove containing his DNA that he had inadvertently dropped at the scene of the Fecarotta slaying.
After two uncredited cameo appearances in The Age of Innocence and Where Evil Lies, his friend Martin Scorsese cast him in the 1995 crime drama Casino as Chicago Outfit boss Remo Gaggi, the film's de facto antagonist and inspired by the real-life Joseph Aiuppa.
An almost exclusive supplier of the Chicago Outfit (although often selling to rival gangs such as the North Side Mob), he was one of the first to supply "Tommy" submachine guns and other specialized weaponry connected to countless gangland slayings during the bootleg wars of the 1920s, including the murder of Brooklyn mobster Frankie Yale in 1928, the St. Valentine's Day Massacre in 1929 and the 1930 gangland murder of Chicago journalist Jake Lingle.
Law enforcement authorities suspected thugs under the control of Bugs Moran, head of the Chicago Mafia.
Alderman Fred Roti and Democratic Committeeman John D'Arco, Sr., both of whom also had close ties to the Chicago Outfit, took their direct orders from Marcy.