The events of New Year's Eve 1958/59 in Havana are portrayed in the film Godfather II which is an interesting blend of fact and fiction with some characters more-or-less directly lifted from history, some semi-, some entirely fictional. In the film, Batista arrives at a New Year's party being attended by his henchmen and mafia partners and announces his resignation.
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Batista's regime did indeed fall on December 31st 1958/1st January 1959 in dramatic circumstances. Batista had underestimated the strength of the Castro rebels who had been holed up in the Sierra Maestra Mountains for almost two years but who were now marching triumphantly towards Havana and carrying the Cuban population with them. By 3rd January parts of the rebel army under Castro's generals Che Guevara and Camilo Cinefuegos had reached Havana; Castro and his troops, with a great sense of theatre and amid scenes of wild jubilation, arrived in Havana on 8th January.
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As the news spread round Havana, anarchy took hold - the people's seething resentment erupting onto the streets and into the casinos, several of which were ransacked with slot machines and gambling tables being dragged out onto the streets and set ablaze.
Most of the leading mobsters in Havana, including Meyer Lanksy (played as Hyman Roth in Godfather II by Lee Strasbourg) did not flee immediately but instead drove round the Havana Casinos colelcting as much of their money as they could, the night's takings that they were able to rescue amounting to several million dollars.
Meanwhile the angry revolutionary crowd continued to ransac the hotels and casinos, even letting a herd of pigs run amock in the most glamorous of the hotels, The Riviera, once the jewel in Meyer Lansky's Havana crown.
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By the end of 1958 he was a hated figure in Cuba - he still had the support of the elite around him including the army but, crucially, he finally lost the support of the US Government who, under Eisenhower, lost patience with his regime. The US felt it had little to fear from Fidel Castro asssuming that if he took power, Cuba would descend into anarchy as it had many times before and open the door for an American intervention or at least for an expanded US role in Cuba.
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Luciano had been deported from the US to Sicily after the war. In the US he had been in jail but had helped the US war effort working for Naval Intelligence and using his influence in the New York Docks and and in Italy to snuff out the traffic in information about ship movements. He snuck back to Havana from Sicily in 1946 and attempted to re-assert his position as 'Capo di tutti capi' working from Cuba. The US government had other ideas and forced the Cuban Government to deport him again in 1947. Luciano died in Naples in 1962.
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One other Havana-related, mob hit that achieved mythical status was that of Albert 'Mad Hatter' Anastasia - one of the more ruthless mob killers and enforcers of the post-war period and head of the band of mob killers known as 'Murder Inc'.
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Anastasia demanded that the arrangements be changed - he was threatening to upset the lucrative equilibrium that Lanksy had created in Havana and to try and muscle in on a bigger piece of the Havana action and his end too was inevitable- though somewhat more shocking given the fear that he created wherever he went.
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There were two other key mafia figures in Cuba in the fifties. Santos Trafficante was from Tampa Florida where is father had amassed a fortune mainly controlling the local street gambling obsession called 'bolita'. Trafficante probably had plans of his own to dominate the gambling scene in Cuba but always had to play second fiddle to Lansky who he deeply resented.
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Trafficante was the owner-operator of the Sans Souci nihgtclub in Havana and probably tolerated the 'upstart' Lansky's position (as he would see it) because it was good for business. He tried in 1957 to outflank Lanksy by doing a deal to invest in Cuba behind Lansky's back with Albert Anastasia which will have further encouraged Lanksy and the other key figure in the Havana Mob, Joe Stassi, to take Anastasia out of the equation which they did two months later.
Trafficante died in Houston, Texas where he had gone for heart surgery in 1987. He was almost certainly involved with the assassination of JFK which, according to his lawyer, he practically confessed to. JFK and his brother Bobby were waging a war on organised crime and JFK himself had also made enemies of many anti-Castro Cubans living in the US after the fiasco of the Bay of Pigs invasion.
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In reality Stassi was a trusted associate of Lansky's. It was to Stassi's house that Lanksy sent all the winnings that he could save as chaos overran Havana on the night of Dec31/Jan1 1959. It was Stassi who travelled to New York in 1957 to organise the assassination of Anastasia.
Lansky, Trafficante and Stassi all stayed on in Cuba after Castro's victory, hoping that once the dust had settled they would be able to re-open their hotels and casinos and that everything would return to normal. They were wrong. Castro shut down or nationalised all the hotels and casinos. Trafficante and Stassi were arrested numerous times throughout 1959 by Castro's rebels who were, by the summer, summarily prosecuting and executing known allies of the Batista regime.
By October 1959 all of them had fled Cuba, losing everything. 'I crapped out' said Lanksy of his Cuban adventure, probably not before amassing a vast fortune, which was never found after he died in 1983 in Florida at the age of 80. Stassi, flat broke after he fled Cuba resorted to drug trafficking and soon ended up in jail where he spent the remainder of his days living to the ripe old age of 95.
Articles
Guardian, 3 Jan 1959
Books
The Havana Mob: How the Mob Owned Cuba ... and Then Lost it to the Revolution - T.J. English
Cuba: A New History (Yale Nota Bene) - Richard Gott
Havana: The Revolutionary Moment - Burt Glinn