SouthernWorldwide.com – On May 20, 1902, the Cuban flag was raised for the first time over an independent nation. More than a century later, the Cuban people remain unfree. Previous U.S. presidents, prior to Donald Trump, either did too little, too much, or nothing at all regarding Cuba. Trump, however, is the first to acknowledge the Cuban regime as a direct threat to America and has resolved to confront it decisively.
The failure of his predecessors to address this issue is not just a tragedy for Cuba, but for the United States as well. Cuba’s communist regime is officially designated as a State Sponsor of Terrorism. It has been responsible for two of the most damaging espionage operations against the U.S. in recent history.
Furthermore, the regime has served as the intelligence backbone for the Maduro narco-state and acted as a central hub for migration flows and drug routes that have impacted American communities. The suffering exported from Havana has tragically resulted in the loss of American lives.
The question arises: how could a small island nation, governed for 66 years by communists unable to maintain its own power grid, cause so much trouble for the world’s most powerful country? The answer lies in the fact that the United States allowed it to happen. The freest, most prosperous, and most powerful nation in history possessed the capability to resolve its “Castro problem” decades ago, but those in power in Washington lacked the necessary will.
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Examining the historical record reveals a pattern of inaction or insufficient action. John F. Kennedy’s administration famously betrayed Cuban-American freedom fighters at the Bay of Pigs. Ronald Reagan and George H.W. Bush treated Cuba as a secondary issue during the Cold War, which concluded without resolving the Cuban situation.
Bill Clinton only signed the Helms-Burton Act after the regime shot down two Brothers to the Rescue aircraft in 1996, resulting in the deaths of four American citizens, and Congress compelled his hand. George W. Bush, meanwhile, accepted the existing status quo.
For decades, American presidents did not do enough to dismantle the Castro regime. Barack Obama, in contrast, pursued a policy that aimed to preserve it.
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Between 2014 and 2017, the Obama administration engaged in what is considered the most reckless diplomatic experiment in U.S.-Cuba relations. Embassies were reopened, and direct flights and cruise lines were initiated. Cuban-American millionaires and billionaires enjoyed luxury in Havana hotels that were off-limits to ordinary Cubans.
A sitting U.S. president was seen participating in the wave at a baseball game with Raúl Castro. The underlying theory was that engagement would empower reformers within Cuba. However, this theory proved to be a fantasy.
The Cuban regime exploited the Obama administration and their associated business figures as “useful idiots,” pocketing their financial contributions. Simultaneously, they imprisoned dissidents like José Daniel Ferrer, the Ladies in White, and artists from the San Isidro movement. The period also witnessed the largest Cuban exodus since Mariel and the brutal suppression of the July 11 protests with Soviet-like tactics.
Every dollar invested flowed through GAESA, the military conglomerate that controls approximately 70 percent of the Cuban economy. Despite warnings, the Obama administration proceeded with its engagement policy.
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Then came Donald Trump. In January, American special operators conducted a flawless raid that resulted in the deaths of Cuban security personnel within Maduro’s protection detail and the subsequent capture of the dictator, who was brought to a federal courtroom in Manhattan. This operation demonstrated to the world that America could once again take decisive action.
Years of patient pressure exerted by President Trump on Venezuela culminated in a swift operation lasting just over two hours. This same methodology is now being applied to Havana. Cuba has once again been designated as a State Sponsor of Terrorism.
The Cuba Restricted List has been implemented to block transactions with GAESA. Title III of the LIBERTAD Act has been reinstated. Executive Order 14404 authorized blocking sanctions on GAESA and the foreign companies that support it. On May 7, the State Department officially designated GAESA itself and the Sherritt joint venture at Moa Nickel.
Raúl Castro has been indicted. Raúl Castro, Miguel Díaz-Canel, and the generals of GAESA are expected to soon learn the same lesson that Nicolás Maduro learned.
A small group, including former Obama-era officials, lobbyists who profited from the engagement period, and academics who built careers defending that policy, continues to advocate for lifting sanctions and attempting engagement again. These individuals are not impartial observers; they are the architects of a failed policy.
Their experiment resulted in enriching GAESA, filling Cuban prisons, and contributing to the largest migration crisis at the American border in a generation. They wish to repeat these actions, but the United States should not grant them another opportunity.
What a reformed Cuba could offer already exists ninety miles away in Florida and across the Caribbean. It includes ordinary Cubans owning restaurants or opening banks, citizens publishing newspapers, and the freedom to voice complaints without fear of reprisal. It means voters who can replace a government that fails them.
No transition supported by the United States in modern history has had the advantages that a new Cuba possesses: a Cuban-American Secretary of State, a Cuban-American congressional delegation, a diaspora ready to lead reinvestment, and a statutory framework specifically designed for this critical moment.
Donald Trump is the first president to recognize the Castro regime as the genuine threat to America that it has always been. He has also chosen the right individual as Secretary of State to assist him in ending it. The Trump Doctrine that concluded Maduro’s rule is now being directed ninety miles south.
One hundred and twenty-four years after the Cuban flag first flew over an independent nation, this president is committed to ensuring it flies over a free one.
Alberto Martinez is a Managing Partner at Continental Strategy in Washington D.C.
