Saturday, April 18, 2026

CUBA: MORE COMPLICATED THAN EVER

 

In January 2019, my spouse and I were privileged to join a Washington County Bar Association cultural exchange. It was a unique continuing legal education program that transported 24 local travelers to Havana, Cuba. Over five days we were treated to a full lineup of lectures on Cuban history, economics, and the socialist political system. We also enjoyed diverse eating experiences, museums, an art colony, and music/dance ensembles.

All of us came away with admiration for the Cuban people. They have been resilient through difficult economic times. Older Cubans were patriotic and grateful for the advances in education, universal healthcare, and social equality achieved under the regime’s vision of communism. On the other hand, younger Cubans complained about the hardships and restrictions. Many seemed eager to receive a Cuban education and then leave the island to live elsewhere.

Following this exhilarating trip, I wrote two commentaries about our excursion for the Observer-Reporter. The first, focused on the Cuban People and their adaptation to socialism following the 1959 revolution. The second, covered the political climate in the beginning of 2019 and the state of Cuban-American relations.

I concluded my commentaries with the thought that “Cuba remains a mystery wrapped in an enigma…and very complicated.” Since Donald Trump regained the presidency, the Cuban story has become even more complicated. This commentary will provide an update on Trump’s policy toward Cuba and what the future might hold.

In January, 2019 Trump was two years into his first term. The previous, Obama administration had taken major steps to reestablish diplomatic relations and to ease the six-decade old embargo against Cuba.

Trump reversed course and placed the relationship with Cuba back on a belligerent footing. Trump believed he needed the political support of exiled Cuban Americans and Florida’s Cuban-American Senator, Marco Rubio, to keep Florida “red” in the 2020 national election.  

As events unfolded in his first term, Trump turned his attention to other issues.  Little additional action was taken against Cuba. Moreover, the Obama initiatives to improve relations were supported by 77% of Cubans born in America.

It was encouraging that a month after our group left Cuba, voters overwhelmingly passed a referendum to reform the Cuban constitution. The referendum kept an authoritarian socialist system in place while adopting several economic, social, and legal reforms.

The lives of most Cubans did not significantly improve during the less hostile Biden administration. The island continued to experience gasoline and medicine shortages. Power outages were common, food costs increased, and the public health system was overwhelmed. However, things were about to get much worse.

Last year, when Trump was sworn in for his second term, the policy toward Cuba dramatically changed. First, the President reversed his campaign pledges of a foreign policy based on “no war, isolationism” to one of attacks on Iran in the Middle East and of gunboat diplomacy in the Western Hemisphere.

U.S. forces began conducting a campaign of airstrikes against suspected drug-trafficking vessels in the Caribbean Sea and Eastern Pacific Ocean. As of March 25, there have been 47 attacks killing at least 163 people.

In Venezuela (Cuba’s main trading partner and source of oil), there was a surprise U.S. military action to remove President Nicolás Maduro from power. The Trump administration now supports a friendlier authoritarian government and has gained control of the country's oil assets. It stopped Venezuelan oil exports to Cuba.

Second, Marco Rubio was appointed by Trump to serve as his Secretary of State. Rubio has long called for a regime change in Cuba. An important goal was to permit Cuban exiles to return to the island and to recover their nationalized assets. Trump began publicly boasting about “a friendly takeover of Cuba.” The President gave Rubio the lead over Cuban policy to implement his long-held goals.

Today, there is almost no electricity or gasoline. Schools suspended classes, and hospitals have canceled surgeries. The country was heading for a major humanitarian crisis until Trump permitted a single Russian oil tanker to dock in Cuba on the last day of March to provide temporary relief.

What happens next? An excellent analysis comes from two Latin American experts on Cuba, Rut Diamint and Laura Tedesco. Their essay, The Coming Showdown Over Cuba, appeared in the March issue of Foreign Affairs. The authors surmise that because the Cuban security forces are well trained and loyal, that an attack similar to Venezuela would be too costly and probably fail.

However, Diamint and Tedesco have concluded that the communist regime that has ruled Cuba since the 1950s is in serious trouble. They see a likely outcome where “Cuba’s leadership may soon be forced to accommodate Washington, bringing the revolutionary era of the last seven decades to a close.”  

There are news reports that Secretary of State Rubio has been in serious talks with Raul Castro’s grandson, Raul Guillermo Rodriquez Castro. He is a younger, more business minded member of the famous family.

What if Trump doesn’t really care about democracy? What if his aim is, like in Venezuela, to work with a Cuban government that will import American products and build Trump hotels? What if permitting the next generation of Castros to become oligarchs, under a business-friendly authoritarian government, achieves this goal?

With this endgame, the wealthy Cuban expats get their land back. However, the citizens of Cuba gain few freedoms. At least they could turn on the lights.

 

 

 

 

 

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