Santo Trafficante Jr
Tampa mob boss - Castro closed his casinoes

Carlos screwed up. We shouldn’t have killed John, We should have killed Bobby.
Santo Trafficante Jr assumed control of the Trafficante Crime Family in 1954 on the death of his father, Santo Trafficante Sr. He operated primarily in the Tampa Florida area and in the nation of Cuba maintaining gambling, prostitution and a variety of other illegal operations.
His reach did not lead to control over Florida's east coast underworld activities but he was closely aligned with Sam Giancana and Carlos Marcello. He also had connections with Meyer Lansky and Bugsy Siegel.
In Cuba Trafficante openly operated is own hotel/casino and apparently had an interest in several others owned, in part, by Lansky.
He was caught up in the Appalachian meeting in 1957 where mob bosses from around the country. This dust up caused the Cuban police to look into his operations even though, prior to this he appeared to have a working relationship with the Batista regime.
In January of 1959, Fidel Castro assumed control of the island nation as Batista believed his survival outlook would improve if he left the country – with millions of dollars. Trafficante tried to negotiate with the new leader, but ultimately he failed and eventually found himself in Cuban prison. He was released they next year thanks to the efforts of his attorney, Frank Ragano. This resulted in his expulsion from the country as an “undesirable alien”.
When CIA agent, Robert Maheu talked to Johnny Roselli about taking out Castro, since they had more confidence in the gangsters ability to do the job than their own men. Roselli introduced Maheu to two men who could help. They were known as Sam Gold and Joe... and they actually were Sam Giancana and Santo Trafficante who was more than willing to help in their efforts to assassinate Fidel Castro.
Trafficante was with Marcello when their mutual attorney, Frank Ragano delivered a message from Jimmy Hoffa that Kennedy needed to be killed. They said nothing but the message was delivered legally because attorney-client privilege.
In a September 1963 conversation with Cuban exile and FBI informant, Jose Aleman, Trafficante was told it looked like Kennedy would be re-elected. His reply was, "No, Jose, he is going to be hit."
During the House Select Committee on Assassinations, Trafficante said he had nothing to do with Oswald and that what he meant was that Kennedy would be hit politically. His reasoning was that the conversation was in Spanish and there were not words to express the difference.
A few days before his death, Trafficante told Ragano that they really meant that Robert Kennedy should be killed. However Marcello's thinking was that you cut off the head of the snake rather than the tail.
The Silent Don: The Criminal Underworld of Santo Trafficante Jr.
by Scott M. Deitch
The Silent Don exposes the life and ruthless times of one of America's most powerful and feared mob bosses. With a criminal empire that stretched from the Gulf Coast throughout the Caribbean, Trafficante was linked to drug trafficking, plots to kill Fidel Castro, and the assassination of JFK. Scott M. Deitche scoured court records, law-enforcement reports, newspaper accounts, and conducted dozens of interviews to find the compelling story of this enigmatic Mafioso don.