Category: Organized Crime

• The Mafia Contract

  A theory that organized-crime bosses ordered the assassination of President Kennedy because Attorney General Robert F. Kennedy aggressively pursued them after the 1960 election, despite claims that mob figures had helped secure political support for JFK. In many versions, the contract theory overlaps with anti-Castro operations and covert contacts already shared by the Mafia and U.S. intelligence.

• The Prohibition Bootlegger Pensions

  A theory that after the repeal of Prohibition in 1933, federal or local authorities secretly paid retired bootleggers, fixers, and Mafia-connected operators to keep quiet about corruption, bribery networks, and political protection that had flourished during the dry years. In rumor form, these payments were described as “pensions,” hush money, or quiet retainers meant to prevent public exposure of officials who had profited from the illegal liquor economy.

• Chicago Mayor Assassination (Anton Cermak)

  The Chicago Mayor Assassination theory held that Anton Cermak was not merely the accidental victim of Giuseppe Zangara’s failed attempt on Franklin D. Roosevelt, but the real target of a contract killing tied to organized crime. In the strongest form, Zangara was either a hired shooter or a useful screen for a more directed hit arranged by interests threatened by Cermak’s anti-racketeering posture and political consolidation in Chicago. The historical basis was real enough to sustain the suspicion: Cermak was wounded during the Roosevelt attempt in Miami on February 15, 1933, later died, and rumors linking the attack to Capone-era underworld politics circulated quickly. The conspiracy version made Miami not the scene of a missed presidential killing, but of a successful gang assassination.

• The Chicago Underground War

  The Chicago Underground War was the theory that Chicago’s hidden freight-tunnel railway, including the small underground electric trains that later folklore sometimes called “Bunnies,” formed a covert logistics network for gangland operations during Prohibition. In the specific St. Valentine’s Day Massacre version, the theory claimed that bodies, weapons, or participants were moved through these tunnels to conceal routes of travel or dispose of evidence after the killings. The historical tunnel system was real: a freight and utility tunnel network built under downtown Chicago, with an early but short-lived mail contract and long-running freight service. The conspiracy version arose by combining that genuine underground infrastructure with the city’s gang mythology and then stretching the tunnel system beyond what is clearly documented in the massacre itself.

• The Beating of the Drys

  The Beating of the Drys was a rumor complex from the late Prohibition era claiming that prominent dry politicians and Anti-Saloon League leaders were not true abstainers at all, but secret drinkers whose private habits were known to organized crime. According to the theory, the mob preserved incriminating evidence, supplied discreet liquor, and used that knowledge to blackmail supposedly upright reform leaders into silence, selective enforcement, or behind-the-scenes compromise. The theory grew in an atmosphere where “drink wet and vote dry” had become a widely recognized accusation, and where scandal, hypocrisy, and corruption were increasingly associated with Prohibition politics. In its strongest form, the story recast the dry movement not as morally rigid but as privately compromised and therefore governable by the criminal underworld.