Standing outside the White House before heading to Texas, Trump told reporters that Cuba is “in deep trouble,” that it has “no money, no oil, no food,” and that Secretary of State Marco Rubio is handling talks at a “very high level.” Then came the headline that sent the media into cardiac arrest. Maybe, he said, we’ll have a “friendly takeover” of Cuba.
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According to reports from outlets like Reuters and the Miami Herald, Rubio or officials close to him have engaged in informal talks tied to figures connected to the Castro family, including Raul Castro’s grandson. The Cuban government publicly denies any high-level negotiations. That is expected. Authoritarian regimes do not confirm weakness in command.
At the same time, the facts on the ground are ugly.
Cuba’s economy is deteriorating fast. The island is struggling with food shortages and rolling blackouts. U.S. pressure has tightened around oil shipments. Venezuela, long a lifeline for Cuban energy, is no longer the dependable ally it once was. When a regime that runs on control can no longer keep the lights on, that control starts to crack.
Add to that a volatile incident this week in which Cuban forces killed four exiles and wounded six after a Florida-registered boat entered Cuban waters and opened fire on a patrol. Rubio denied any U.S. government involvement. Still, the episode underscores how tense and unstable the moment is.
So when Trump talks about a “friendly takeover,” it is not a random fantasy. It is a leverage language. He is describing a country on the ropes.
For over six decades, Cuba has stood as a stubborn relic of Cold War communism just 90 miles off our coast. We tried isolation. We tried normalization under Obama. Neither delivered freedom to the Cuban people. The regime endured, but the people endured more. I witnessed this myself on a mission trip to Havana in 2018. We traveled throughout the country delivering supplies to churches that had suffered at the threat of the government.
Now the regime is wobbling.
The question is what America does when wobbling turns into collapse.
Trump’s framing is blunt. That is his style. But behind it is a strategic reality. When a hostile government in our hemisphere is economically failing and seeking relief, the United States holds cards. Serious ones.
A “friendly takeover” does not have to mean Marines on the beach. It could mean a negotiated transition tied to massive economic assistance. It could mean lifting certain sanctions in exchange for structural reforms. It could mean supervised elections, property restitution, and a gradual integration into Western markets.
Or, if talks fail, it could mean nothing at all..
But to pretend this is outrageous to even discuss is naive. Cuba is not across an ocean. It is in our backyard. When it destabilizes, we absorb the consequences. Migration surges. Criminal networks move. Foreign adversaries sniff for influence. Russia and China would love to exploit a vacuum in Havana.
Leadership requires anticipating that vacuum.
There is also a domestic angle that cannot be ignored. The Cuban American community, especially in South Florida, has carried the memory of exile for generations. Families lost businesses, homes, and churches. They fled with nothing. For them, the idea of a free Cuba is not theoretical. It is personal.
Trump referenced those Americans who would welcome change. Rubio embodies that connection. A Cuban American leading diplomatic engagement sends a message both to Havana and to Miami. This is not amateur hour. It is targeted.
None of this guarantees success. The Castro era has proven stubborn before. The Cuban military and security services still hold power. And regimes under pressure often lash out, as this week’s deadly maritime clash suggests.
Cuba is weaker today than it has been in years. Its economy is strained. Its alliances are fraying. Its people are restless. In moments like this, history can pivot quickly. The real bones of it all are strategic pressure meeting structural decay. If the United States can guide that decay toward a peaceful transition instead of chaos, that would not be imperial. It would be consequential.
For sixty years, Havana defined itself in opposition to America. Now it may be forced to negotiate with it.
The phrase “friendly takeover” may be provocative. But the underlying reality is simple.
When a failing communist regime starts talking, Washington should listen carefully. And if there is an opening for freedom just 90 miles from Florida, we should not be afraid to step through it.
