Why All the Fuss About Cuba?

The Focus on Cuba

Cuba has been a focus of the Trump administration since the capture of Nicolas Maduro, then President of Venezuela, on January 3, 2026. Venezuela had been a large support system for Cuba, and after Maduro’s capture, the U.S. was able to pull that Venezuelan support and apply new pressure to Cuba. Cuba is an island nation just 90 miles south-southeast of Florida. That location makes Cuba an important element in the United States’ strategic power and security.

Cuba had been a colony of Spain from 1492 until the Spanish-American War and Spain’s defeat in 1898. At that time, the U.S. became a protectorate of Cuba, which lasted until the Cuban revolution in 1959, at which time Fidel Castro took power and shifted Cuba into a communist state aligned with Russia. U.S. assets that had been in place in Cuba were stolen and nationalized by the Castro regime. The U.S. response was to sever diplomatic relations with Cuba and enact an economic embargo.

The Cuban Missile Crisis

The Castro regime maintained close ties with Russia that ultimately led to the showdown with the U.S. in 1962, in what we now call the Cuban Missile Crisis. The crisis was created when Russia and its leader, Nikita Khrushchev, began delivering short and medium-range missiles to Cuba for installation and potential use against the United States. Then President John F. Kennedy took the missile placements very seriously and threatened Russia with attacks if those missiles were ever made operational. Without going into too much detail, the crisis ended when the U.S. agreed not to invade Cuba and Russia removed the missiles. That firmly set the path of relations with the U.S. and Castro on a bad note.

That relationship stayed consistent right up until the fall of the Soviet Union in 1991. With that collapse, support for Cuba from the Soviet Union ended, and Cuba fell into a severe economic depression. It was after this that Cuba found new support from Venezuela. The leaders of the two countries became close and worked to support each other.

The Monroe Doctrine

In 1823, then President James Monroe issued what is known as the Monroe Doctrine, which spelled out the idea that the Western Hemisphere was overseen by the United States and that European powers should not interfere in any affairs in this territory.

President Donald Trump has been talking about shifting U.S. attention from the Eastern Hemisphere and back to the Western Hemisphere in what some people have called the “Donroe Doctrine”. It is this concept that led to the capture of Nicolas Maduro and has his attention on Cuba. In essence, Donald Trump wants Latin American and Caribbean nations to have stable democratic governments and close relationships with the United States. He is currently trying to improve relations with Venezuela and wants to do the same in Cuba, though that will likely require some kind of regime change away from Communism.

Increased Pressure

Cuba is currently ruled as a totalitarian one-party communist state by the Communist Party of Cuba (PCC). The current President is Miquel Diaz-Canel. He was handpicked by former President Raúl Castro, who replaced Fidel in 2006 due to health issues. The strong ties to the Castros will make regime change difficult.

To try to get the regime to notice how serious President Trump is about getting better aligned with Cuba, he initiated a blockade that is preventing fuel shipments from getting to Cuba. This has resulted in a significant energy crisis on the island. President Trump has referred to Cuba as a failed state because of its economic problems and social repression. The embargo continues to push Cuba further into its economic and energy crisis.

Trump has threatened military action to remove President Canel from office and instigate regime change. After the successful military operation to capture Nicolas Maduro, it’s certainly possible this could happen. But we believe Trump is more willing to allow the island to continue its downfall and allow Cuban residents to dismantle the current regime.

The Good News

The good news here is that if President Trump succeeds in improving relations between Cuba and the U.S., the economic benefits would be substantial. U.S. companies could establish operations in Cuba, and tourism from the United States would flourish. Cuba would gain access to multiple products and services it currently lacks, and its future would be much better. Changing direction after nearly seventy years will be a real challenge, but President Trump seems to think it is possible and will be a significant benefit to Cuban residents.

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Barron Financial Group, LLP is a fee-only Registered Investment Advisor regulated by the Securities and Exchange Commission.

This newsletter is for general information only and should not be considered investment advice.  Investors should consult with a trained investment professional to discuss their particular situation.

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