Like almost everything else in Havana, the old Tropicana hotel and casino seems frozen in time. When I visited Cuba two years ago, the hotel was undergoing renovations, but its façade and interior lobby had not changed much since mobsters such as Meyer Lansky, Lucky Luciano, Frank Costello, Sam Giancana, and Santo Trafficante Jr. hung out in its nightclub. They mixed there with celebrities including Marlon Brando, Marilyn Monroe, Frank Sinatra, Rita Hayworth, Humphrey Bogart, Ingrid Bergman, and Errol Flynn. Even John F. Kennedy, then a senator from Massachusetts, made frequent appearances. The cars parked in its lot were some of the latest models for 1958, shortly before Fidel Castro seized the country. The Hotel Nacional is busier with tourists drinking Cristal beers or sipping mojitos in its garden, served by state-employed waiters who could never afford the cocktails they make.
Talking to retired Cuban officials is like talking to Iranian diplomats, former ministers, and office heads. Many pay lip service to the revolution, but their eyes betray the emptiness of their platitudes. They know they represent a desiccated corpse and no longer believe the principles for which they once stood.
While Cuba’s president is 65-year-old Miguel Díaz-Canel, Cuba’s first leader born after the 1959 revolution, Cuban officials acknowledge that a troika of old guard leaders, including 94-year-old Raúl Castro, run the country behind the scenes. Should President Donald Trump seek to replicate a Venezuela-style operation, the chief difference would be that the Cuban people would gladly push their dictators out, though U.S. forces might need to roll them away on wheelchairs rather than simply frog-marching them onto helicopters.
Trump has been flippant about what comes next in Venezuela. He suggested the United States would run the place, but there is no indication he is serious. Indeed, Trump appears fine with hard-line socialist and Maduro acolyte Delcy Rodriguez taking over.
The U.S. cannot afford to be so lackadaisical should Cuba’s government fall. Many Cubans also seek to preserve their culture and heritage. Indeed, Cuba feels far different from other Caribbean countries, and Cubans fear that American and European developers will destroy that which makes Cuba special. In the 1950s, Cuba had become a hub for organized crime. When the communist regime ends, there will be a scramble for Cuba’s future. It could be a goldmine for a new generation of criminals and hustlers. As a real estate developer, Trump salivates at erecting new hotels and resorts on prime beachfront, but even anti-regime Cubans fear foreign interests taking over the island.
A hands-off approach to governance could be worse. Cuba has suffered a tremendous brain drain over the past two years, with more than 10% of the country, disproportionately elite white Cubans, fleeing, mostly to the United States. While communist Cuba long denied racism, Afro-Cubans remained second-class citizens. Many Cubans fear a power vacuum could lead to gang violence and a scramble for territory among competing factions. Here, Haiti’s experience is germane: The 30-year Duvalier dictatorship brought security to the island through repression, but, when Jean-Claude “Baby Doc” Duvalier fled among growing pressure, Haiti spiraled into chaos.
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If Trump ousts the communist regime, Cubans will celebrate both at home and in exile. But the decisions Trump makes now about post-regime change governance will determine whether post-communist Cuba becomes a new Puerto Rico or a second Haiti.
A dismissive, hands-off approach by Trump in Cuba may substitute one fading threat for an entirely different one that could undermine regional security for decades to come.
Michael Rubin is a contributor to the Washington Examiner’s Beltway Confidential blog. He is the director of analysis at the Middle East Forum and a senior fellow at the American Enterprise Institute.