When the Mob Ruled Havana – Cigar Aficionado

In February of 1947, Frank Sinatra arrived in Havana, Cuba, holding a suitcase filled with $2 million in cash. He was flanked by two mobsters from Chicago, the Fischetti brothers, Rocco and Charlie.

The brothers were cousins of Al Capone, with long-standing reputations in the businesses of illegal gambling and killing. As bodyguards they were second to none—tough, loyal and connected at the highest levels of the Mob, which, at the time, was more robust and powerful than it had been since the glory days of Prohibition.

Sinatra knew all this. As a fellow traveler of the Mob since his childhood in Hoboken, where the bent-nose “cafones” and aspiring wiseguys were a vibrant part of the local landscape, the singer had an affection for Mafiosi that bordered on idolatry. They took care of him, and he took care of them. This was why, arriving in Havana with a heavy, undeclared fortune in his possession, Sinatra was not overly concerned.

The Hotel Nacional staff had been alerted, though names were not mentioned. The hotel was one of the city’s most prestigious addresses, where celebrities were commonplace. But no one was supposed to know that Sinatra would be staying there (he checked in under a false name), nor did they know the real name of the man to whom Sinatra was delivering his cash-laden suitcase: Charles “Lucky” Luciano.

Sinatra and Luciano went way back. The bond between the legendary organized crime figure and the singer was based partly on their ancestry from the same small town in Sicily. Furthermore, the story goes, Luciano had helped Sinatra out by settling some old debts and, more importantly, helping him out of an onerous contract with a famous bandleader. Frank was forever after indebted to the Honored Society.

Weeks before Sinatra’s arrival, a who’s who of the American Mob had gathered in Havana for a major conference, presided over by Luciano and his closest gangster associate, Meyer Lansky. Sinatra’s cash delivery to Luciano constituted operational expenses for the Mob. Some of it would grease the wheels of corruption in the Cuban government; some of it would cover Luciano’s living expenses in Havana; and some of it would cover lavish meals for the mobsters as well as choice rooms at the Hotel Nacional, a Moorish/Sevillian/Art Deco palace perched on a bluff overlooking the aquamarine Gulf of Mexico.

The international star was but a bit player in this saga, the dimensions of which he likely knew little. The cash he had delivered was seed money for one of the most grandiose ventures the American Mob would ever undertake: to establish a base of operations in Cuba that would make it possible for organized crime to function as an international conglomerate. Fulfilling this plan would put the Mob beyond the reach of U.S. law enforcement.

For many years, the story of the Mob in Havana would be relegated to folklore and fictionalization. The most popular version was The Godfather Part II. The Francis Ford Coppola film, which won the 1975 Academy Awards for best picture, best director and a host of other categories, devotes about 25 minutes of its three-hour-and-twenty-minute running time to Cuba. But those scenes are indelible for anyone who has seen the movie. Though fictionalized, the movie accurately captures the mood of Havana during the time of the Revolution, and even contains a scene that is based on the Mob conference of 1946. In the movie, a handful of mobsters gather on a sunny hotel rooftop to celebrate the birthday of an aging Hyman Roth, a Jewish mobster from New York who is in the midst of forging a partnership with a corrupt Cuban president. A birthday cake frosted with an image of the island of Cuba is sliced up, and the pieces are distributed among the assembled mobsters.

It was understood even at the time of the film’s release that Hyman Roth was based on Lansky. A boyhood friend of Luciano and other seminal early 20th-century Mob bosses, Lansky was a Russian Jew with a good head for numbers. The portrayal of Meyer as the key architect in organized crime’s attempted takeover of Cuba was correct, but, in truth, Lansky in Havana was not an old man in ill health. He was in his mid-40s, the prime of life for a Mob boss. His efforts were focused and vigorous, as he sought to realize a dream that began in the days of Prohibition.

The conference lasted for days, and some 23 high-ranking mobsters from around the U.S. took part. Supposedly, the decision to kill, or whack, Benjamin “Bugsy” Siegel, a lifelong friend of both Luciano and Lansky, was made then, based on the belief that Siegel had been skimming money from the construction budget of the Flamingo Hotel in Las Vegas. Among other things, the conference reestablished Luciano—who had spent more than a decade in prison before being freed, then deported to Italy—as the de facto CEO of the Mob. His reemergence wouldn’t last long. Within days of the conference, the U.S. government learned that Luciano was in Havana. The Justice Department pressured the Cuban government to send him back to Sicily, which it did in March 1947.

On the surface, the deportation of Luciano seemed like a blow for the Mob and its plans of a criminal base of operations in Cuba, but the opposite was true. The real brains behind the plan was Lansky. At the Mob conference, Luciano had given Lansky’s plan his full approval and made sure each of the gangster bosses signed on. But Lansky knew that Luciano was headstrong. Since the 1920s, Lucky had made much of his fortune from the smuggling of heroin, and Lansky did not want the Mob to have anything to do with narcotics in Cuba. He saw it as a threat to his view of an empire built almost entirely on casino gambling.

With Luciano out of the way, Lansky could begin to formulate the kind of operation he had in mind for Cuba, one that was based on casino gambling, which was his forte. Even so, it would take another five years for all of the pieces to fall into place. The man who made it possible—Lansky’s partner in the plundering of Cuba—was none other than the president himself, Fulgencio Batista.

Since the landing of Christopher Columbus in 1492, Cuba has been at the crossroads of many events of international consequence. This history is best personified in the city of Havana, which, to this day, is populated with more spectacular buildings and architectural flourishes than most any city in the Americas. Though much of it has fallen into disrepair, the ancient ruins of Havana still cast a spell, giving the city an air of great import.

In the mid-20th century, few men understood the inner workings of Havana better than Batista. He had been born and raised on the opposite side of the island, in the cane-cutting municipality of Banes, in the province of Holguin. His beginnings were humble. At a time when black people and those of mixed race had little access to social advancement he was mestizo, the latter. But Batista had many traits that made him stand out: he was a hard worker in the cane fields; he also worked on the railroads and as a tailor, mechanic, charcoal vendor and fruit peddler. In 1923, when he joined the Cuban Army, he quickly distinguished himself through his personal discipline, his dedication and his leadership abilities. By 1933, through a rebellion within the ranks of the military known as the Sergeant’s Revolt, Batista—just 32 years old—emerged as the de facto head of the Cuban military.

Throughout Cuba’s history, political turmoil was the norm. Presidents came and went at a stupefying rate. One president lasted five days in office. Others were toppled through military coups and violent uprisings. The military, not elected officials, emerged as the true power in Cuba. Which is why Lansky, as far back as 1933, set his sights on Batista.

According to Joseph “Doc” Stacher, a friend and associate of Lansky’s since their childhood together on Manhattan’s Lower East Side, he was present on a day in 1933 when Lansky presented Batista with multiple suitcases filled with cash. In later meetings, Batista was given a guarantee of $3 million to $5 million a year, in exchange for a monopoly on casino gambling. Batista was also promised a cut of the profits.

Lansky and Batista shook hands on this deal, but it would be close to two decades before the arrangement could be consummated.

In 1940, Batista was elected president of Cuba. During his term, he played a pivotal role in instituting the country’s first constitution. This was a great point of pride for all Cubans. For Batista, though he was still relatively young, it was the crowning achievement of his career. So filled with a sense of accomplishment was Batista that he didn’t run for a second term as president. Instead, he retired to Daytona Beach, Florida, where he divorced his first wife and married his longtime mistress.

Within months of the 1946 Mob conference in Havana, Lansky visited Batista in Daytona Beach and once again made a pitch: We need you back in Cuba. Everything is in place for us to achieve what we talked about many years ago.

Batista’s return to Cuban politics was not pretty. Initially, he was elected senator in absentia from Las Villas province. In 1951, he ran for president, but just weeks before the election, a poll in the weekly magazine Bohemia showed him running a distant third in the race. Batista had clearly lost popularity with the national electorate, but he still held sway over the true ruling authority on the island: the military.

On March 10, 1952, the military seized control of all radio stations and newspapers in Havana. Tanks and other combat vehicles drove through the city to the presidential palace, where then-President Carlos Prío Socarrás was given the option to vacate the office of the presidency. Facing insurmountable odds, Prío fled with little resistance. Batista took over.

One of Batista’s first directives as president was to appoint Lansky—one of America’s premier gangsters—as his adviser on gambling reform. It wasn’t as perverse as it sounds. The reputation of casino gambling in Cuba had hit the skids when Dana Smith, a financial advisor to Sen. Richard Nixon of California, claimed that he’d been scammed at the San Souci, one of Havana’s better-known nightclub-casinos. Nixon wrote a letter to the U.S. State Department asking them to look into Smith’s claims. The State Department contacted the U.S. embassy in Havana, which launched an investigation into claims that gambling in Cuba was rife with scams and illegalities.

Lansky was brought in to clean up the mess. He fired many of the dealers and brought in new ones from his “carpet joints” (illegal casinos) in South Florida, upstate New York and from his legal casinos in Las Vegas. He enforced rigid gaming regulations. Behind Lansky’s reforms was a simple premise: casinos needn’t rip people off to turn a huge profit. Especially in Havana, where there was no gaming commission, casino gambling was a license to print money. The Mob was the gaming commission.

The Mob’s reign in Havana was relatively brief, lasting from 1952 to 1959. It is now remembered as a storied era, with many legendary anecdotes and a colorful cast of characters, but at the time it was happening, very little of the goings on were reported in the U.S. press. Part of Cuba’s allure was that, even though it was just 90 miles off Florida, it was a foreign country outside the focus of American media. If there was a motto, it was: What happens in Havana, stays in Havana.

It had always been the Mob’s plan to use entertainment as a draw to bring potential customers to Cuba. But what took place, even the Mob couldn’t have predicted. Indigenous Cuban culture—a vibrant, colorful mix of Afro-Cuban music and secret religious societies such as Santería and Lucumí—became the inspiration for an entertainment scene that was, by most accounts, mind-blowing. Nightclubs became known for elaborate floor shows based on expressions of local culture. The showgirls were statuesque and exotic, and their costume changes tended to reveal voluptuous physiques and dreamy skin tones. The dancers—male and female—were magnificent. This style of entertainment would eventually become most commonly associated with Las Vegas, but it started in Havana.

The music was often torrid, aggressively rhythmic and symphonically sophisticated, though the Havana Post, the island’s only English-language newspaper, often described it as “hot voodoo music” with an emphasis on the primal. At the Tropicana, the house band was led by Bebo Valdes, one of the most renowned composers on the island. Afro-Cuban music and Latin jazz existed at every level of the nightclub scene, from the fancy nightclubs to cocktail lounges, hotel bars and, especially, the late-night clubs where the scene became physical and sweaty, where tourists from Duluth and Akron were known to lose themselves and throw caution to the wind.

Sex, of course, was a big part of the draw: commercial sex, love, lust, extramarital sex, gay sex—you name it. It’s hard to know how much of this was planned by the mobsters. Havana had always been a sexual crossroads in the Caribbean, since the time of pirates and smugglers. But in the 1950s, the sheer originality, sexiness and spontaneity of the scene elevated things to a level not experienced since the Belle Époque in Paris.

The best brothels in town were not owned or run by the Mob. A woman known as Doña Marina had a series of upscale bordellos, including Casa Marina, a three-story building in Habana Vieja (Old Havana). El Templo de Marina was located alongside the Prado, one of the city’s premier locales for strolling.

All of these establishments were a stone’s throw from the Sevilla Biltmore, a classy Spanish-style hotel and casino, built in 1908. It was owned by Amleto Battisti, an Uruguayan of Italian ancestry who was an important associate of Lansky’s and other reigning Mob bosses in Havana. Because he was not American, Battisti was immune to Lansky’s prohibition on dealing narcotics. If you wanted marijuana or cocaine in Havana, it was sold at Longchamps Restaurant inside the Hotel Sevilla Arcade.

Along with the gamblers and tourists came the celebrities. By the mid-1950s, rumors abounded around the globe that the city of Havana was the place to be. The Mob’s involvement in the casinos and nightlife was not exactly a secret. When television host Steve Allen broadcast “The Steve Allen Show” live from Havana, he opened by saying to his viewers, “Welcome to Havana, Cuba, home of the pineapple and Meyer Lansky.”

The presence of the Mob had become part of the attraction. You could maybe rub shoulders with a notorious crime figure at a casino or nightclub in Havana, and no cop or federal agent was ever going to question you about it. The discreetness of it all was appealing to celebrities, who usually came during the winter and made the place feel like the Monte Carlo of the Caribbean.

Given the larcenous nature of organized crime, detailed Mob-authorized ledger books are like the Dead Sea Scrolls, impossibly rare and difficult to interpret. It’s hard to know exactly how much was being generated in the way of profits. Some of the money was funneled back into local operations, such as Lansky’s dream project, the Riviera, built for $14 million in 1957 (the equivalent today of $125 million). The hotel was self-financed by the Mob, like the Capri, the Deauville and others.

The biggest benefactor of all may have been Batista. Every Monday at 12 noon, a bagman was allowed into the presidential palace through a side door. He carried with him a satchel filled with cash, part of a monthly payment of $1.28 million that was to be delivered to the president. It was all so glorious that it should have lasted forever. Why would anyone shut this down?

But far outside of Havana, things were not all well. Since Batista had taken over the country in a military coup, many had not accepted him as a legitimate leader. Rumblings of dissent led to revolutionary activities, most notably the 26th of July Movement, led by Fidel Castro. Starting in 1955, that movement had been winning hearts and minds and gaining victories against the Cuban Army, mostly in the eastern part of the island.

Havana was far removed from these activities, but still, indications were that the Revolution was no joke. The chief of SIM (Servicio de Inteligencia Militar), Batista’s notorious military intelligence police, known for torturing and killing political dissidents, was assassinated in the lobby of the popular Montmartre nightclub and casino (owned by Lansky). Two months later, a bomb was set off by a young female revolutionary at The Tropicana nightclub. Many were injured; the bomber herself lost an arm. The violence was instilling fear and terror.

It may have worried Lansky as well. In 1958, in a series of secret meetings, he traveled to the Dominican Republic to meet with Rafael Trujillo, a Caribbean dictator with an even tighter stranglehold on his country than Batista. Lansky was putting out feelers about the possibility of moving the entire Havana operation to the DR. But it was too late.

It all came crashing down on New Year’s Eve. Lansky was with his driver at a party at the Plaza Hotel when an underling approached and whispered in his ear. The words caused Lansky to flinch. Batista had fled the country in the dead of night. Castro’s revolutionary guard was advancing toward the city.

“Get the money,” Lansky ordered. He knew that if the revolutionaries were to flood into the city without resistance, the first thing they would do is go to the counting rooms of the casinos and seize the cash. The mobsters frantically rounded up millions of dollars and took it to a central location, hoping they could safeguard the money until they found a way to get it off the island. They were only partially successful. Their decades-long investment in Cuba as a gangster’s paradise was over. What they had created in Havana over the last six years had gone up in smoke. The mobsters scampered.

Batista is believed to have absconded with $300 million, much of it having been transferred to Swiss bank accounts in the week leading up to New Year’s Day. In a safe in his office was $3 million in cash, which the revolutionaries found and showed off at a press conference. Apparently, Batista didn’t need it. Perhaps he left it behind as a tip.

The casinos were shut down, and then, for a time, reopened. The mobsters negotiated with Castro, but when the new rulers made it clear there would be monitors in the counting rooms of the casinos, the jig was up. Rebels in the counting rooms? You can’t have rebels in the counting rooms. That’s where the money is stolen.

The Cuban casinos were permanently closed, all assets seized by the provisional Cuban government.

The American Mob took a huge hit—in prestige, pride and, most of all, financially. In Cuba, they made the ultimate gamble—and lost. As Lansky himself put it years later, trying to explain what happened: “I crapped out.”

T.J. English is the author of Havana Nocturne: How the Mob Owned Cuba And Then Lost it To the Revolution.