This piece argues that the United States finally has a president willing to confront the Cuban dictatorship, reviews the long pattern of U.S. mistakes on the island, and explains why renewed pressure and accountability are the right path for liberty, regional stability, and American security.
For more than six decades Cuba has been a source of misery for its own people and a threat to the region. The island’s rulers exported repression, backed bad actors, and enabled migration and drug flows that hit American communities hard. The United States could have acted decisively generations ago, but presidential timidity and misguided experiments let the Castro system grow bolder.
History matters here. From Bay of Pigs betrayals to Cold War complacency, Washington’s record is full of half measures and missed chances. Engagement without leverage only enriched the regime’s military businesses and punished dissidents. That is why a different approach was needed, one that treats the island as a national security problem and a moral one.
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When pressure became policy, results followed. Cuba sits on the State Sponsor of Terrorism list because its intelligence services and military-linked conglomerates enabled corruption, narco-networks, and espionage. Those activities didn’t stay across the water; they bled into American streets and strained border security. Confronting that network is not politics, it’s protecting citizens.
The Obama-era opening was sold as a humane move toward reform, but the facts tell a different story. Diplomacy without consequences handed cash to GAESA, the military conglomerate that dominates Cuba’s economy, while human rights activists were jailed and protests crushed. Tourism dollars flowed to the regime, not to the courageous people pushing for change, and the exile community watched the experiment fail.
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Donald Trump shifted the posture to one of pressure and accountability, and his team applied the lessons learned in Venezuela. Tactical operations exposed how deeply Cuban security forces had embedded themselves in Maduro’s protection, proving American capability and resolve. Sanctions targeted GAESA and its partners, Title III of the LIBERTAD Act was enforced, and indictments signaled that bad actors would face consequences.
There will always be those who argue for another engagement experiment, often the same people who profited or earned careers off it. Their view ignores the jail cells, the migration waves, and the hard truth that money funneled into state coffers fuels repression. We should be skeptical of policies that reward dictatorships while bleeding the Cuban people of hope.
What makes this moment different is the presence of a ready alternative inside reach. Cuban Americans and the wider diaspora stand prepared to lead a free transition, with proven business experience and political will. Political institutions, rule of law, and civil society already exist nearby in Miami and across the hemisphere, offering a model for what Cuba could become once tyranny is removed.
The strategic case is simple: ending the regime’s power structure helps reduce terrorism sponsorship, disrupts narcotics networks, and eases migration pressures. It also restores America’s moral standing by backing those who risk everything for freedom. This approach mixes pressure with support for civil society, not naiveté and tourism dollars that subsidize repression.
Washington’s job is to back the brave, not bolster the brutal. Treating Cuba as the threat it is means sustained pressure on the regime’s financial arteries, legal action against its leadership, and coordination with allies and the diaspora on a post-regime recovery plan. The goal is straightforward: make freedom possible, and protect the United States while doing it.
