The Florida Godfather Who Tried To Kill Castro

They called him the "Silent Don" because he lived an unassuming lifestyle, but Florida Godfather Santo Trafficante Jr. was as ruthless as they come.

Santo Trafficante Jr. was a reserved, modest man married to the same woman for 49 years. But he was also the most powerful crime boss in pre-Castro Cuba, with influence that extended into Florida and the rest of the United States.

Trafficante was jailed and deported when Fidel Castro rose to power, leading him to spend a good portion of his adult life hatching a plan of revenge. According to some, he was even involved in the infamous assassination of President John F. Kennedy.

So, who was this so-called “Silent Don” who wielded enough power to allegedly kill the President?

The Rise Of Mafia Don Santo Trafficante

Getty ImagesSanto Trafficante was wanted in 48 states by the time he was 43.

Born in Tampa, Florida in 1914, Trafficante hailed from a family already deeply involved in organized crime.

Like many of the most prominent mobsters of the 20th century, his father, Santo Trafficante Sr., grew up in Sicily, Italy but became a major player in the criminal world after migrating to America. As such, Trafficante Sr. controlled gambling rackets for bolita, a lottery game popular in Florida and Cuba, until 1940 when the murder of Tampa boss Ignacio Antinori pushed the Trafficantes to assume ultimate power in the Florida underworld.

Zeng8r/Wikimedia CommonA set of bolita balls.

By this point, Trafficante Jr. had fully taken over the oversight of drugs shipped between Florida, Cuba, and the rest of the United States. His positioning in Florida was prime for drug shipping as the product often passed through these ports en route to elsewhere in America.

Trafficante proceeded to open casinos in Cuba at his father’s behest and facilitated heroin smuggling by working together with famous mobsters Charles “Lucky” Luciano and Meyer Lansky.

From A Prince To A Kingpin

In 1950, the aging Trafficante Sr. began to slow down. He sought treatment for stomach cancer and was ready to hand power over to a trusted lieutenant. Who better than his son, Trafficante Jr., to inherit his throne?

Trafficante Sr. passed away four years later, leaving Jr. his Tampa and Cuba-based criminal empire. While the senior Trafficante had been a major mobster in his own right, nobody could have expected the heights that were going to be reached by his son.

Santo Trafficante Jr. continued to develop his interests in Cuba serving as Luciano and Lansky’s local liaison. Meanwhile, he continued to make money from the drugs that came through Tampa.

Trafficante along with 56 other mobsters was arrested in New York while discussing what to do about the recent death of Gambino family head, Albert Anastasia. That arrest also led Cuban authorities to become wary of the mobster, especially as the political tides seemed to be turning there.

Despite his arrest, Trafficante managed to escape charges and continue to fly under the law’s radar. That was in part due to his lifestyle. Interestingly, Trafficante — who was worth about $25 billion at his height in the ’80s — lived a fairly reserved, modest lifestyle. He drove standard cars, lived in regular houses in quiet places, was married to the same woman, and generally described as a quiet man.

Harris & Ewing/Library of Commons/Wikimedia CommonsCuban leader Fulgencio Batista in Washington, D.C. in 1938.

Trafficante Jr. was nonetheless a ruthless and old-school mob boss. This was proven in 1953 when he eliminated the last contender to the Tampa mob throne: Joe Antinori, son of the late Ignacio.

With that act, Santo Trafficante now reigned supreme in Tampa. He moved to Cuba in 1955 where he met the country’s authoritarian ruler Fulgencio Batista. Batista let Trafficante and other mobsters build as many casinos and hotels as they wanted in exchange for a cash kickback.

Trafficante’s partnership with Batista was profitable for both parties and so the mobster’s fate became inextricably tied to that of Cuba’s political climate.

The Silent Don’s Cuban Connections

When Fidel Castro began his ascent to power in the 1950s, Santo Trafficante feared the radical Marxist revolutionary wouldn’t cooperate with him. He was right, and when Castro took power in 1959, Trafficante’s burgeoning gambling-and-drugs empire went under siege.

Trafficante tried to win Castro over to his side, but that didn’t work. Trafficante had now not only lost an ally but a significant portion of his income as his casinos were closed by the Marxist revolutionary.

In a 1978 legal testimony, Trafficante discussed how quickly Castro shut it all down, then reopened the casinos on his own terms. After that, he ordered casino owners to cough up employee back pay, then shut them down again.

Peter Moruzzi/Wikimedia CommonsThe glamorous casino in the Hotel Nacional De Cuba in Havana in 1958.

More importantly, Castro imprisoned Trafficante and then had him exiled from Cuba. The mobster would later testify:

“I got news that Cuban officials were looking for to put me in jail because one of the things was that I was a Batista collaborator. They raided my apartment, they were looking for money, they tore up all the furniture, they used to come and get me at nighttime, take me out in the woods, trying to tell where I had my money, this and that, until I finally went into hiding.”

Though his prison sentence wasn’t long and he returned to a strong position in Florida, Trafficante never forgave Castro. Upon his return to the United States, he became determined to bring down the man who ended his empire.

Santo Trafficante’s Plots To Kill Fidel Castro

Trafficante’s chance came in the 1960s when he became acquainted with mobster John “Handsome Johnny” Roselli. Claiming association with the CIA, Roselli knew of Trafficante’s vendetta and told his new pal that the U.S. government also wanted to take down Castro’s Communist regime.

Getting in bed with Trafficante and other leading members of America’s organized crime seems like a strange thing to do for the CIA. But considering the fiercely anti-Soviet atmosphere of the Cold War, it’s not that hard to believe.

For the U.S. government, it was a classic case of “the enemy of my enemy is my friend.”

Ed Giorandino/NY Daily News Archive via Getty ImagesSanto Trafficante arrives at Queens Supreme Court in Kew Gardens.

Alongside Chicago boss Sam Giancana, Roselli and Trafficante came up with some truly insane plots to kill Fidel Castro. Their plans ranged from simply shooting him to having him smoke poisoned cigars or drinking a tainted milkshake.

But those weren’t even their most ridiculous ideas. The mobsters also attempted to get Castro into a poisoned wetsuit and even offered to blow him up with an exploding seashell.

Finally, after the infamous failed Bay of Pigs Invasion, the CIA gave up on their attempts to kill the Cuban dictator and thus Trafficante’s attempts at revenge never materialized.

A Conspiracy To Assassinate John F. Kennedy?

The American government’s close ties to Santo Trafficante Jr. and the Mafia didn’t end with their attempts to kill Castro. In the 1960 presidential election, Kennedy family patriarch Joe Kennedy Sr. used his ties to organized crime to secure votes for his son, John F. Kennedy. According to the account of Judith Exner, however, one of JFK’s many mistresses, it was she who introduced Kennedy to Chicago boss Giancana.

However the meeting came to be, the mob nonetheless brought influential states like Illinois into the Kennedy fold in exchange for the White House going easy on organized crime.

Wikimedia CommonsPresident John F. Kennedy, FBI Director J. Edgar Hoover, and Attorney General Robert F. Kennedy

But once Kennedy actually entered the White House, he didn’t live up to his end of the bargain. His new attorney general — his beloved brother, Robert F. Kennedy — went after organized crime with a vengeance. He convicted infamous criminal labor union head, Jimmy Hoffa.

Robert F. Kennedy even taunted those mobsters he brought into court, telling Chicago mob boss Sam Giancana that “I thought only little girls giggled, Mr. Giancana.”

President John. F. Kennedy not only failed to deliver on his promise to the mob but also actually put the Mafia under increasing pressure. So, as the popular theory goes, the mob bosses that lent a helping hand in getting Kennedy into office wanted revenge.

In 1963, the Mob allegedly had enough of Kennedy. As Jimmy Hoffa’s former lawyer Frank Ragano would later recall, “Jimmy told me to tell [New Orleans boss Carlos] Marcello and Trafficante they had to kill the president. Hoffa said to me, ‘This has to be done.'”

Dennis Caruso/NY Daily News Archive via Getty ImagesFrank Ragano and Santo Trafficante Jr. (right).

The idea behind the assassination wasn’t just to punish JFK but also to get his brother off the Mob’s back.

To add further credence to this theory of JFK’s assassination, famed prosecutor Vincent Bugliosi (who also wrote the infamous true crime novel on the Manson Family, Helter Skelter), who penned Reclaiming History: The Assassination of President John F. Kennedy, quoted a witness who said that New Orleans boss Marcello had quipped:

“The dog [JFK] will keep biting you if you only cut off its tail [RFK].”

The assassination of JFK caught on film.

The final piece of evidence for the theory that Santo Trafficante was involved in JFK’s assassination was a witness who reported that the mobster had once said himself that JFK “not going to make it to the [1964] election. He was going to be hit.”

As we all know, he was right, and Kennedy was assassinated by a sniper in November 1963.

Whether or not a Mafia conspiracy was behind the assassination of President Kennedy is still up for debate. But according to declassified documents released in 1992, Santo Trafficante Jr. made a deathbed confession of his involvement in the President’s murder.

The Testimony Of Santo Trafficante

Fifteen years following the assassination, Trafficante testified in front of the United States House Select Committee on the murder of JFK in exchange for immunity. The chairman cited a confession from Roselli that Trafficante’s allies organized a sharpshooter, Lee Harvey Oswald, to take out the President.

But before Trafficante testified, someone conveniently killed Roselli.

In his previous statements, Roselli also tied Lee Harvey Oswald’s killer, Jack Ruby, to Santo Trafficante. Santo Trafficante then categorically denied every allegation about stating he wanted RFK or JFK dead — and got off scot-free.

Jack Ruby shoots Lee Harvey Oswald.

After the Kennedy hubbub, Trafficante kept a low profile — or, lower that is.

The authorities continued to charge him with participating in illegal activities, but the aging mob boss escaped conviction each time. Finally, in 1987, Trafficante died at the age of 72.

Today, Santo Trafficante’s criminal legacy lives on through his nephew and namesake, Santo Trafficante III, who was charged with organized fraud in 1992. Trafficante was one of the last surviving members of the original Luciano mob era upon his death, and the truth behind the JFK assassination may have perhaps died with him.

After this look at Santo Trafficante Jr., read the gruesome story of the murderous American dentist, Benjamin Salomon, of World War II. Then, check out these photos of the aftermath from some of the bloodiest mob hits.

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