Notorious Criminals & Outlaws Codexery

John Roselli

Mobster who aided CIA in Castro assassination plots.

John Roselli, born Filippo Sacco in Italy in 1905, immigrated to Boston as a child and later changed his name after fleeing a narcotics arrest in Massachusetts. He became a key figure for the Chicago Outfit, first working for bootleggers in Los Angeles, where he bribed local officials and ran vice rackets including prostitution and gambling. After meeting Al Capone in 1927, Roselli was brought into the Chicago organization to oversee Capone’s investments and coordinate with the Los Angeles crime family. He also worked on offshore gambling ships and, through friendships with film producers, entered the movie business, receiving producer credits on early gangster films. During the corrupt administration of Los Angeles Mayor Frank L. Shaw in the 1930s, Roselli acted as a liaison between city hall and underworld figures, securing bribes that helped solidify the local Mafia’s power. In the 1940s, he was convicted of labor racketeering for extorting Hollywood figures and served prison time. By the 1950s, Roselli had shifted his focus to Las Vegas, becoming the chief representative for the Chicago and Los Angeles mobs, ensuring casino revenues were skimmed for the bosses. After the Cuban Revolution, Fidel Castro closed mob-run casinos, and Roselli, along with other mobsters, became willing to assassinate Castro. In 1960, the CIA recruited an ex-FBI agent to approach Roselli, who then participated in the agency’s assassination plots. Roselli later testified before the Church Committee about these attempts.

born
July 4, 1905, in Esperia, Lazio, Italy
nationality
Italian-American

Lore & Background

Roselli was born Filippo Sacco on July 4, 1905, in Esperia, Lazio, Italy. He immigrated to Boston at age six with his mother, after his father had moved to the United States first. In 1922, he was arrested on narcotics charges in Massachusetts, fled to New York, then Chicago, where he changed his name to John Roselli. He worked for bootlegger Tony Cornero, bribing Orange County officials, and later went independent, becoming involved in prostitution and gambling. Roselli also became a film producer at Eagle Lion Studios and was friends with Columbia Pictures co-founder Harry Cohn. In the 1930s, Roselli became the liaison between Los Angeles Mayor Frank L. Shaw's corrupt administration and the city's underworld, helping Jack Dragna's organization become preeminent. By the mid-1950s, Roselli became the Chicago and Los Angeles mob's chief representative in Las Vegas, overseeing casino revenue skimming. The plots involved poison pills but failed.

Reader's Guide

John Roselli's significance lies in his dual role as a high-ranking mobster and a CIA asset in Cold War covert operations. His involvement in the CIA's assassination plots against Fidel Castro illustrates the intersection of organized crime and U.S. intelligence during the early 1960s, a period marked by the failed Bay of Pigs invasion and ongoing tensions with Cuba. His career also reflects the mob's expansion into Hollywood and Las Vegas, where he facilitated skimming operations and maintained corrupt ties with local government. Roselli's mysterious death, likely a mob hit, underscores the violent consequences of his underworld and intelligence entanglements. His legacy remains a cautionary example of the blurred lines between national security and criminal enterprise.

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Frequently Asked Questions

Who is John Roselli?

John Roselli, born Filippo Sacco on July 4, 1905, in Esperia, Lazio, Italy, was an Italian-American gangster who rose through the Chicago Outfit and later became an unwitting operative for the CIA. He is best remembered for his involvement in a covert plot to kill Cuban dictator Fidel Castro.

What was Roselli's role in the Chicago Outfit?

As a senior figure in the Chicago-based organized crime syndicate, Roselli helped extend the Outfit's financial and political reach into the entertainment industry in Hollywood and the casino operations along the Las Vegas Strip. His connections gave the mob a foothold in two of America's most visible commercial sectors.

How did Roselli get involved with the CIA and the Castro assassination plot?

The CIA recruited Roselli, leveraging his mob contacts and access to resources, to help orchestrate an attempt on Fidel Castro's life during the early 1960s. Roselli was not fully briefed on the scope of the operation and later expressed shock at having been used as a front for a government assassination scheme.

How did John Roselli's life end?

Roselli vanished on July 28, 1976, and his decomposed body was discovered on August 7 of that year. The circumstances surrounding his disappearance and death were never fully resolved, and his death is widely attributed to retaliation within the criminal underworld.

Why is John Roselli historically significant?

Roselli's testimony before the Church Committee in the mid-1970s exposed the disturbing overlap between U.S. intelligence operations and organized crime, bringing national attention to how the CIA had exploited mob figures for covert actions. His case remains a key example of the murky intersection between government power and the criminal underworld in the Cold War era.

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