The Unlikely Alliance: Crime and Country
Few relationships in American history are as bizarre and troubling as the covert partnership between the Central Intelligence Agency and organized crime figures. During the Cold War, national security concerns led federal intelligence officials to make a Faustian bargain with some of the nation’s most dangerous criminals. What emerged was a shadowy collaboration that would remain largely hidden from the American public for decades.
Operation Mongoose and the Cuban Connection
The most documented intersection of mob and CIA activity centered on Cuba and Fidel Castro. After the failed Bay of Pigs invasion in 1961, the CIA launched Operation Mongoose—an aggressive covert campaign to assassinate Castro and destabilize his regime. Desperate for operatives with connections in Cuba and the Caribbean, CIA officials turned to an unexpected source: the American mafia.
The agency’s logic was ruthlessly pragmatic. Organized crime syndicates controlled extensive networks in Havana, Miami, and throughout the Caribbean. Before Castro’s revolution, crime bosses like Meyer Lansky had operated lucrative gambling and smuggling operations throughout Cuba. These criminals possessed the infrastructure, contacts, and willingness to conduct illegal operations that the CIA theoretically could not undertake directly.
Sam Giancana and the Castro Assassination Plots
The CIA’s primary mob contact was Sam Giancana, the ruthless boss of the Chicago Outfit. Beginning in 1960, CIA operatives met repeatedly with Giancana and his associates to coordinate assassination attempts against Castro. The plots ranged from poisoned cigars to exploding seashells—schemes that read like dark comedy but represented deadly serious intent.
Giancana was willing because Castro’s revolution had cost the mob millions in lost gambling revenue. Here was an opportunity to reclaim those losses while simultaneously serving American Cold War interests. Between 1960 and 1965, the CIA and mob conducted multiple murder plots against the Cuban leader. None succeeded, but the partnership revealed just how far government officials would go in the name of national security.
Lansky, the CIA, and International Operations
Meyer Lansky, the Jewish mob genius who had built a criminal empire spanning from Al Capone’s era through the post-war period, also maintained connections to American intelligence. Evidence suggests Lansky’s international smuggling and money laundering networks were occasionally leveraged for intelligence purposes. His operations in Miami, the Caribbean, and Latin America provided valuable information gathering opportunities during the Cold War.
Lansky’s financial sophistication and global reach made him uniquely valuable to intelligence agencies seeking covert financial operations. While the full extent of their collaboration remains classified, documents and testimony indicate that Lansky’s operations occasionally intersected with CIA activities, particularly regarding Latin American affairs.
The Broader Mob-Government Nexus
The mob-CIA connection wasn’t limited to Cuba. The relationship reflected a broader pattern of cooperation between organized crime and government agencies dating back to World War II. During that conflict, the Office of Naval Intelligence made deals with Lucky Luciano and other mob bosses to secure the New York waterfront against Nazi sabotage. Frank Costello and other Gambino family members provided intelligence and security services.
These wartime alliances normalized the idea that law enforcement could make deals with criminals when “national interests” were at stake. The CIA inherited this mentality, expanding it throughout the Cold War.
The Kefauver Hearing Revelations
Ironically, while the CIA was making deals with mobsters, Senator Estes Kefauver was conducting his famous investigations into organized crime. The Kefauver Hearings exposed the scale of mob influence in American life, yet federal authorities possessed evidence of their own agencies’ complicity that remained hidden from the public.
The Price of Convenient Corruption
The mob-CIA relationship had profound consequences. By outsourcing dangerous operations to criminals, the government gained plausible deniability while simultaneously legitimizing and enriching organized crime figures. The mob extracted favors, protection, and legitimacy in exchange for their cooperation.
More troublingly, this partnership corrupted law enforcement itself. FBI agents, local police, and prosecutors found their investigations stymied when they threatened to expose mob activities that CIA officials considered operationally useful. The code of omerta—organized crime’s code of silence—now had an unlikely ally in the federal government.
The Long Shadow
The full extent of mob-CIA cooperation remains unknown. Declassified documents have revealed only portions of the relationship, and many records remain classified. What we do know suggests that Cold War imperatives led intelligence officials to subordinate traditional law enforcement concerns to geopolitical strategy.
The partnership between organized crime and the CIA stands as a stark reminder that government institutions, when driven by fear and pursuing power, can become corrupted by the very criminals they ostensibly exist to combat. In choosing to work with the mob, American intelligence agencies didn’t defeat organized crime—they strengthened it.