Just how much the Outfit dominated every facet of society at the height of its ubiquity can be difficult to fully grasp. On one end of the spectrum was a quotidian but gobsmacking genre of naked corruption: a retired Chicago police detective relayed to me a story of mobsters walking straight into a precinct with an envelope of cash and exchanging it for reams of criminal records and murder files related to Outfit members, a practice so common that it made countless unresolved killings by the mob nearly impossible to investigate. On the other end was a brand of clandestine kingmaking out of a Dick Tracy strip. Take the illegal wiretaps orchestrated by J. Edgar Hoover that picked up a discussion between Giancana and his associates. A former Chicago FBI agent named William F. Roemer Jr. wrote in his 1989 tell-all Man Against the Mob that Giancana planned to help win the election for then-candidate John F. Kennedy in exchange for “[backing] off from the FBI investigation of Giancana.”
Exactly how the Outfit generated its social, political, and economic power is rarely discussed. The obvious answer is money, of course, but plenty of syndicates have generated illicit profit without achieving total primacy. In fact, the Outfit was almost accidentally Marxist insofar as it understood the innate push and pull between the owners of the means of production and those who toil in service of it. In its initial rise during the Great Depression, it was believed that Outfit-organized labor czar, Murray “the Camel” Humphreys, purportedly oversaw more than sixty-one unions. Such tactics would be extended to far-off lands like Hollywood, where control of the stagehand union enabled bosses in Chicago to extort the captains of show business, an industry that they did not prohibit from producing sensational gangster movies. It was through their hijacking of labor power, not in some smoke-filled room of wise guys, that the fulcrum of their power rested. After all, it was the very same Murray, per Seymour Hersh’s book The Dark Side of Camelot, who coordinated with the Teamsters to get the vote out for Kennedy in the 1960 presidential election. It was a technique familiar to those at the Kennedy compound in Hyannis Port; both Robert and Jack had overseen a 1957 United States Senate Select Committee to investigate mob influence in labor unions. The Kennedys’ patriarch had clearly taken notes.