Can Cuba Be Freed?

Posted on Tuesday, February 10, 2026
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by Robert B. Charles
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Cuba has had a sordid, sad past. That may change soon. After decades of domination by the communist Soviet Union, then life-and-death dependence on communist Venezuela, the fortunes of Cubans could – within the coming year – shift markedly, toward genuine freedom.

The nutshell version of Cuban history is one of suppressed rights – Spain’s colonial conquest and dominance, followed by freedom and mismanagement, followed once again by communist dominance, ruthless dictatorship, death, deprivation, and a sense of hopelessness.

US efforts to pry loose the communists, starting with the “Bay of Pigs” disaster under President Kennedy in 1961, a US-supported effort to insert Cuban exiles into leadership, and follow-on efforts to induce a shift, have all come to nothing.

Cuba’s last hundred years have been tortured. A protectorate of Spain until 1898, the US ended Spanish rule that year. US President Theodore Roosevelt granted Cuba independence in 1902, only to have Soviet-supported communists take over in 1959.

When President Kennedy’s attempt to restore Cuban exiles failed in 1961, the Soviets leaned in – planting surface-to-air missiles on the island, 90 miles from Florida. This created the near-nuclear “Cuban Missile Crisis,” de-escalated by Kennedy, after an economic blockade was imposed.

Fast forward to 1991, when the collapse of the Soviet Union ended the historic economic support Cuba’s communists had enjoyed. Within Cuba, times got hard and, while President Obama lightened US sanctions on the communists, the nation struggled.

In the 2000s through 2010s, communist oil-producer Venezuela stepped into the breach and became Cuba’s patron, effectively keeping the communist government in place to present.

Suddenly, things are changing – and fast. After President Trump snatched the narco-terrorist and communist leader of Venezuela for trial in the US, Cuba began to shiver, at least figuratively. The communist government’s longstanding oil source, Venezuela, has now been cut off.

While a formal blockade – or as Kennedy called it, a quarantine – has not been imposed on Cuba, its oil supply is now drying up. Certainly, China and Iran could risk becoming the communist nation’s new patron, but given the strength and resolve of the US now, that is unlikely.

So, what happens next? While others may seek to ally with Cuba, the likelihood – especially with a reassertion of the historic “Monroe Doctrine” by Trump, making the US a protector of freedoms in this hemisphere – is low. Likely, the Cuban communist government will begin to face shortages.

Since trade with the communist nation will be frowned upon, and sanctions may rise – including against any country aiming to rescue the communist state – we may actually see the goals once articulated by Theodore Roosevelt – a free Cuban people – under discussion again.

Three takeaways are worth mentioning.

First, without President Trump’s decisive leadership – and opposition to communism in this hemisphere, reminiscent of both JFK and Reagan – this potentially bright future for Cuba’s beleaguered, oppressed people would not be even vaguely possible. It is now.

Second, a chess game is afoot, with China, Russia, and Iran watching the unfolding of this potential end of an oppressed country – and implicit ally of theirs – on our doorstep.

If President Trump manages to negotiate – with economic power – freedom for Cuba, hope will spring eternal. Countries around the world will see a renaissance of democratic freedom.

Third, if the use of economic power, reinforced by the restored US role as the world’s only superpower, works in this island country, Americans could hear calls for a 51st state in earnest. The Cuban-American population in America already is 2.4 million – bigger than 13 US states. 

Bottomline: Keep your eyes on Cuba, and on the trend line being established by President Trump. Cubans – a major voting block in the US – would be ecstatic about a free Cuba were a Trump legacy.

Robert Charles is a former Assistant Secretary of State under Colin Powell, former Reagan and Bush 41 White House staffer, Maine attorney, ten-year naval intelligence officer (USNR), and 25-year businessman. He wrote “Narcotics and Terrorism” (2003), “Eagles and Evergreens” (North Country Press, 2018), and “Cherish America: Stories of Courage, Character, and Kindness” (Tower Publishing, 2024). He is the National Spokesman for AMAC. Today, he is running to be Maine’s next Governor (please visit BobbyforMaine.com to learn more)!

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