On December 31, 1958, Fulgencio Batista left Havana for the last time, reportedly with hundreds of millions of dollars on the nation’s cash in his pockets.
On January 9, 1959, the man who would replace him as long-time (and unelected) leader of Cuba, Fidel Castro, rolled into the capital and a new era began.
This 1963 photo of Castro shows him as a man of action, fighting out in the countryside.
Cuba’s big neighbour - Florida is less than 100 miles away - had a lot of opinions about what Castro should do next.
So apparently did the Mafia bosses who owned the casinos that made Havana an off-shore gambling paradise for American tourists.
What neither of them wanted was what happened:
Castro expropriated the casinos and started emptying Mafia bank accounts in his country.
Although he didn’t openly declare himself a communist or socialist straight away, he was soon nationalising sugar, fruit and oil businesses with US cash behind them.
Even then, perhaps the US and Cuba might have been able to find an amicable way forward.
But then things went seriously wrong.
Castro started to do deals with the Soviet Union.
At the height of the Cold War.
A Cuban flag owned by Castro. At first it seemed possible to US observers that Castro was a Cuban nationalist, but he soon aligned his country with the Soviet Union.
The US was secretly funding opposition. Castro’s government was becoming less tolerant of dissent.
Finally, in March 1960, as Wikipedia puts it: “President Eisenhower authorized the CIA to overthrow Castro's government. He provided them with a budget of $13 million and permitted them to ally with the Mafia, who were aggrieved that Castro's government closed down their brothel and casino businesses in Cuba.”
And so starts a decades long campaign to kill Fidel Castro.
Who tried to kill Castro?
There are several parties to these plots.
They are:
The United States Government.
In 1976, the United States President Gerald Ford issued an executive order that was an admission. From that point on, Executive Order 11905 said: “No employee of the United States Government shall engage in, or conspire to engage in, political assassination.”
US President Gerald Ford made a promise and also a confession.
This was vague enough that it had to be sharpened up by President Carter a few years later, removing the “political” qualification.
The Ford order was produced in response to the work of the Church Committee, whose examination of what the CIA had been up to included finding eight assassination plots against Fidel Castro.
To say the US tried to overthrow the Cuban government and kill its president (whatever you think of their legitimacy) is no conspiracy theory, it’s well-documented fact.
Anti-Castro Cubans
The US has a lot of money.
So, as a man with a hammer sees every problem as a nail to be hammered in, a state with basically limitless finances throws them around to solve its problems.
A lot of US money was spent on what are usually referred to as “Cuban exiles”, but should also include anti-Castro Cubans inside the country.
Watergate burglar Virgilio Gonzalez was not the only anti-Castro Cuban exile in the crew.
That isn’t to say that there was no genuine resistance to Castro and his government. There was.
Some of it was independent and some was financed and helped by the US government, most famously in the case of the Bay of Pigs invasion.
The Mafia
Also working alongside the CIA were, well, the world’s most famous crime syndicate.
John Roselli, Sam Giancana and Santo Trafficante have all been named in official US government documents as coconspirators in Castro assassination plots.
Santo Trafficante in Havana before the Revolution.
Roselli (nicknamed “Handsome Johnny”) was a mobster in the Chicago branch of the Mafia known as the Outfit, that was run by Sam Giancana. Santo Trafficante ran the Tampa, Florida gang and much of the Mafia’s Cuban holdings.
Beyond approaches made to these men there isn’t much of an official record.
But there’s plenty of talk.
What did they do?
Historians should beware of men bearing colourful anecdotes and in search of book contracts.
So, perhaps some of the more out there stories around attempts to kill Castro have been given extra spice in the tellling.
The Church Committee investigations found shooting plots.
Sam Giancana wanted to poison Fidel.
Bombs in cigars?
Fidel's cigar box was signed, which meant no-one else should touch it because he feared a bomb or poison in his beloved Cuban cigars.
That’s the most popular story, and we know Castro took it seriously enough to have special personal arrangements to smoke safely.
Cuban officials have subsequently claimed to have been aware of 638 separate plots to assassinate Castro.
Undoubtedly some - like a 2000 attempt to blow him up in Panama - were genuine and posed a real threat.
It became something of a brand for Castro, who reportedly said: "If surviving assassination attempts were an Olympic event, I would win the gold medal."
He died aged 90 in 2016. Of natural causes. In his sleep.
Cuba and America
The echoes of the Cuban Revolution sound loudly through modern American history.
There’s a compelling narrative linking the revolution through the Bay of Pigs to the Kennedys, then to their assassinations, and finally to the Watergate scandal, when Cuban exiles were among the men arrested for attempting to bug the Democratic Party on behalf of President Nixon.
A popular retelling of the Kennedy Assassination has it as a revenge job by the CIA, the Mafia and Cuban exiles for John F Kennedy’s failure to fully back the Bay of Pigs operation.
Was John Kennedy killed because of his Cuba policy?
Cuba is still a big issue in Florida (where most Cuban exiles settled) and it plays a role in every presidential election.
Collecting Castro and 60s politics
Cuba is relatively closed to the world.
Certainly Americans will have trouble buying there.
So, if you want to collect Castro you’ll likely find a somewhat constrained supply.
Though we were lucky enough to source a major collection relating to him.
American politicians mentioned here: Kennedy, Nixon, are all highly collectible, and fine subjects for your collecting focus.
Documents, signatures, campaign material, media... they are all available.
The Mafia? Well, that’s a different story perhaps. It would certainly be very easy and rewarding to start a collection on the organisation in popular culture.
Collecting political memorabilia today
When does politics become history?
Our mailbag suggests people still care very deeply about the events covered here.
