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The Mafia and Cuba: 75 Years of History

Sugar Mill

Cuba has long endured foreign influences ranging from conquest and military interventions to investment and tourism. During the past centuries, Cuba’s prolific sugar fields brought huge sums of overseas investment, as Americans were Cuba’s main sugar trade clients based on our ravenous appetite for sugar in the daily diet. Sugar was freely bartered by the thousands of tons to U.S. customers in exchange for every U.S. product that ordinary Cubans might want or need, from toothbrushes and shoes to the essential staples of rice, beans, milk and meats.

Following Cuba’s Fidel Castro-led revolution in 1959, Russia primarily supported Cuba, utilizing the island’s strategic proximity for international diplomacy and an implied military threat during the Cold War. However, for one sensational decade prior, in the late-1940’s and 50’s, another menacing group found its profitable home on the island. Mobsters, primarily New York criminals, realized Havana was the ideal “fantasy” destination from which they could operate and realize huge untaxed returns unfettered by laws on the U.S. mainland.

Mafia influence in Cuba had been initially focused on smuggling drugs and alcohol into the United States. During Prohibition mobsters would “rum-run”, while cocaine and heroin addictions rose simultaneously. Mob bosses at first refrained from the illicit drug trade, but for some Dons, the lure of big-time profits was too great to resist. Illegal drugs entered Cuba from South America, Asia and North Africa, as Cuba was often the transshipment point before the final journey to American cities. Establishing in Cuba enabled the Mob to store drugs before the “coast cleared” for final transshipments to the U.S.

Cuban border and customs officers were easy to bribe. Cuban President Fulgencio Batista, a “U.S. puppet President”, became well-acquainted with big-time mobsters from the U.S., offering support for Mob operations in the form of country-wide police protection in exchange for a healthy cut of profits. Following his self-imposed exile from Cuba during the 1940’s, the notorious New York gangster Charles “Lucky” Luciano returned to Cuba when Batista resumed power at the end of that decade, to be joined by mobster financier Meyer Lansky. Luciano and Lansky would soon gain control of Cuba’s gambling industry and build its casinos, setting the stage for the island’s gambling boom of the 1950’s.

Following his own flight from the FBI, who were on the trail of illegal gambling operations in Las Vegas, Luciano organized the notorious “Havana Conference” comprised of major Mob bosses in Cuba. The Conference brought together heads from Cosa Nostra’s (the Mob’s) “Five (ruling) Families” for discussions on ways to carve up Cuba’s heroin trade, casino control and illicit drug industries. Mobsters’ “cover” for trips to the island was singer Frank Sinatra, Cuba’s immensely popular “crooner in residence”.

Starting with Batista’s resurgence to lead Cuba through a seizure of power with American support in 1952, rebels began taking foot led by the soon-to-become Revolutionary hero Fidel Castro. Castro’s return following an exile in Mexico in the mid-1950’s, overall public outrage at Batista’s excesses culminated in 1959 with Castro’s ability to overthrow the government and establish the nation as a fledgling Communist country. Batista had fled the country with his life, taking hundreds of millions with him. As the new Castro regime took hold, capitalists were given chase, imprisoned or worse, casinos were looted and mobsters fled back to the U.S. “mother ship”. Lansky, once the mega-millionaire gambling kingpin of Cuba, lost nearly all his wealth and reportedly died relatively destitute.

In the end, Mafia hotels and casinos were seized and nationalized by the new government, as were American-owned and/or controlled businesses, warehouses and commercial interests on the island. Gambling was outlawed and Cuba would enter a prolonged period of economic malaise, destitute without American business but proud of what it had achieved to benefit the great majority of its citizens.

Hotel Nacional

While mobsters were forced to flee Cuba leaving their enterprises behind, the beautiful hotels they built still stand today, operating in varying states of repair. For visitors to the island, taking a look at these relics of Cuba’s dangerous but vibrant Mafia past is a lesson in how unbridled lawlessness plus eager local partners-in-crime destroyed the lives and hopes of ordinary people.

The resilient Cuban people today, however, have increasing hopes for a return to some degree of prosperity since Raul Castro, in 2008, began offering licenses to thousands of private businesses. Generations under socialist/communist rule compelled Cubans to share what little they had with each other. Entrepreneurship and a rising Cuban middle class of tourism-related Cuban business people (“cuentapropistas” – entrepreneurs) through tourism, bring new hope and opportunities to their families.

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