The east coast of Florida was a loosely knit conglomerate of New York family interests with links to Meyer Lansky, Bugsy Siegel, Angelo Bruno, Carlos Marcello, and Frank Ragano.

Trafficante was arrested frequently throughout the 1950s on various charges of bribery and of running illegal bolita lotteries in Tampa's Ybor City district.

During the rule of Cuba's authoritarian dictator Fulgencio Batista, Trafficante openly operated the Sans Souci Cabaret and the Casino International gambling establishments in Havana.

[5][6] Cuba was one of the Apalachin topics of discussion, particularly the gambling and narcotics smuggling interests of La Cosa Nostra on the island.

In addition, "on January 23, 1958 the Cuban Department of Investigation, Havana, Cuba notified the Bureau of Narcotics that Santo Trafficante was registered in their Alien Office under No.

The "Family Jewels" confirmed that in September 1960, the CIA recruited ex-FBI agent Robert Maheu to approach the West Coast representative of the Chicago mob, Johnny Roselli.

[9] The CIA and the Mafia had a common enemy in Castro, a communist revolutionary who had shut down Cuba's lucrative casino businesses.

"[11] Aleman claimed to have reported Trafficante's comments to his FBI contacts, who "dismissed the Kennedy warnings as gangland braggadocio.

"[11] In 1978, both Trafficante and Aleman were called to testify before members of the United States House Select Committee on Assassinations investigating possible links between Kennedy assassin Lee Harvey Oswald and anti-Castro Cubans, including the theory that Castro had Kennedy killed in retaliation for the CIA's attempts on his own life.

[12] On September 27, 1978, Aleman reiterated to HSCA investigators that Trafficante had complained to him for hours in June or July 1963 about Kennedy's crackdown on organized crime at a meeting to discuss a business loan.

[13] The HSCA had previously quoted Aleman as stating that he thought Trafficante's use of the phrase "he is going to be hit" meant that the mob boss knew Kennedy was going to be killed.

[13] After a grant of immunity from prosecution, Trafficante testified before the HSCA the following day, September 28, and denied the allegation that he told Aleman that "Kennedy was going to be hit.

[14] Ragano also claimed that Trafficante, four days prior to his death, delivered a deathbed confession which suggested that Marcello was meant to assassinate Robert F. Kennedy instead of his brother, the President.

[19] In 2005, Lamar Waldron and Thom Hartmann's book Ultimate Sacrifice said that Trafficante was behind an aborted plot to kill Kennedy in Tampa on November 18, 1963.