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On May 20, 1902, the Cuban flag flew for the first time over an independent country. One hundred and twenty-four years later, the Cuban people are still not free. Every president before Donald Trump either did nothing about Cuba, did too little, or did too much for the regime. Trump is the first to recognize that the regime is a threat to America itself and to resolve to confront it once and for all.
That his predecessors failed to do so is not only the Cuban people’s tragedy. It is ours. Cuba’s communist regime is a designated State Sponsor of Terrorism. It ran two of the most damaging espionage operations against the United States in modern memory. It was the intelligence backbone of the Maduro narco-state. It has served as a coordinating hub for the migration flows and drug routes flooding American communities. The suffering Havana exports has cost American lives.
How was it that a small island nation, run for sixty-six years by communists who could not keep their own power grid running, was allowed to cause so much trouble for the most powerful country on earth? Because the United States allowed it. The freest, most prosperous, and most powerful nation in history could have solved its Castro problem decades ago. The men who held power in Washington lacked the will.
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Consider the record. John F. Kennedy betrayed Cuban-American freedom fighters at the Bay of Pigs. Ronald Reagan and the elder Bush treated Cuba as a secondary file in a Cold War that ended without resolving it. Bill Clinton signed Helms-Burton only because the regime shot down two Brothers to the Rescue aircraft in 1996, killing four American citizens, and Congress forced his hand. The younger Bush accepted the status quo.
For decades, American presidents did too little to end the Castro regime. Barack Obama did the opposite: he tried to save it.
From 2014 to 2017, the Obama administration ran the most reckless engagement experiment in the history of U.S.-Cuba relations. Embassies reopened. Direct flights and cruise lines launched. Cuban-American billionaires and millionaires sipped daiquiris in Havana hotels ordinary Cubans are barred from entering. A sitting American president did the wave with Raúl Castro at a baseball game. The theory was that opening would empower reformers. The theory was a fantasy. The regime treated the Obama administration and their businessmen buddies as useful idiots, pocketed their money, jailed José Daniel Ferrer, the Ladies in White, and the artists of San Isidro, presided over the largest Cuban exodus since Mariel, and crushed the July 11 protests with Soviet brutality. Every dollar flowed through GAESA, the military conglomerate that controls roughly seventy percent of the Cuban economy. The Obama team was warned. They proceeded anyway.
Then came Donald Trump.
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When American special operators executed a flawless raid in January that left Cuban security personnel dead inside Maduro’s protection detail and the dictator himself in a Manhattan federal courtroom, the world learned that America can do things again.
Years of President Trump’s patient pressure on Venezuela ended in two hours and twenty-eight minutes. The same methodology is now being applied to Havana. Cuba is again a State Sponsor of Terrorism. The Cuba Restricted List blocks transactions with GAESA. Title III of the LIBERTAD Act is back in force. Executive Order 14404 authorized blocking sanctions on GAESA and the foreign companies that prop it up; on May 7, the State Department designated GAESA itself and the Sherritt joint venture at Moa Nickel. Raúl Castro is now indicted. Raúl Castro, Miguel Díaz-Canel, and the generals of GAESA will learn the lesson Maduro learned soon enough.
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A small chorus of former Obama-era officials, lobbyists who pocketed fees during the opening, and academics who built careers defending engagement continues to argue for lifting pressure and trying again. They are not neutral observers. They are the architects of a failed policy. Their experiment enriched GAESA, filled Cuban jails, and drove the largest migration crisis on the American border in a generation. They want to do it again. We do not owe them another chance.
What is on offer in a new Cuba already exists ninety miles away in Florida and across the Caribbean. Ordinary Cubans owning a restaurant or opening a bank. Citizens running a newspaper. Complaint that is not a crime. Voters who can replace a government that fails them. No transition the United States has supported in modern history has had what this one does: a Cuban-American Secretary of State, a Cuban-American congressional delegation, a diaspora ready to lead reinvestment, and a statutory framework designed for this exact moment.
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Donald Trump is the first president to treat the Castro regime as the threat to America it has always been, and he chose the right man as Secretary of State to help him end it. The Trump Doctrine that ended Maduro’s reign is now turning ninety miles south. One hundred and twenty-four years after the Cuban flag first flew over an independent country, this president will make sure it flies over a free one.
Alberto Martinez is a Managing Partner at Continental Strategy in Washington D.C.
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