Trump's 'Friendly Takeover' of Cuba: Carrot, Stick, or Pipe Dream?

"Maybe we'll have a friendly takeover of Cuba." With those words on February 27, President Donald Trump added another chapter to America's complex relationship with its communist neighbor just 90 miles from Florida's shores. But can you really "friendlily" take over a sovereign nation while simultaneously choking its economy?

The Carrot and Stick Approach

Trump's Cuba strategy reads like a masterclass in contradictory diplomacy. On one hand, his administration has ratcheted up economic pressure to levels not seen in decades. On the other, it's dangling humanitarian aid and potential cooperation.

The escalation began January 3 with a military operation against Venezuelan President Nicolas Maduro, Cuba's key ally. Thirty-two Cuban soldiers died in the attack, marking a dramatic shift from diplomatic to military pressure. Trump followed up by cutting off Venezuelan oil supplies to Cuba on January 11, then threatening tariffs on any country that supplies oil to the island.

Yet simultaneously, the administration announced $6 million in humanitarian aid in February and this week revealed a "favorable licensing policy" for Venezuelan oil resales to Cuba—with the crucial caveat that no transactions can involve the Cuban government or its military.

Cuba's Impossible Choice

For Cuba, Trump's approach presents an existential dilemma. The island's energy grid depends heavily on fossil fuels, and with oil supplies cut off, the UN has warned of potential humanitarian "collapse." The pressure is working—if Trump's claim that "the Cuban government is talking with us" is accurate.

Miguel Diaz-Canel, Cuba's president, has responded with defiant rhetoric, calling Trump's fuel blockade an attempt "to strangle the Cuban economy" and evidence of "fascist, criminal, and genocidal" behavior. But behind the tough talk, Cuba faces harsh economic realities: no money, no oil, and a population that has already seen nearly 2 million people flee during the COVID-19 pandemic.

The tension escalated further this week when Cuban forces engaged in a deadly shootout with a Florida-tagged speedboat near its shores. Cuba called it "infiltration for terrorist purposes," while the US denied responsibility.

The Monroe Doctrine Gets a Trump Makeover

Trump's Cuba gambit fits into his broader vision of American expansion, which he's branded the "Donroe Doctrine"—a not-so-subtle play on the 19th-century Monroe Doctrine. Since his 2025 inauguration, he's proposed "owning" Gaza, "running" Venezuela, and pressuring Greenland, Canada, and Panama to cede sovereignty.

During this week's State of the Union, Trump touted the Venezuela operation as a success, claiming the US had secured over 80 million barrels of Venezuelan oil. "We're also restoring American security and dominance in the Western Hemisphere," he declared.

But UN human rights experts have pushed back, arguing that Cuba poses no "unusual and extraordinary threat" to US national security. They've characterized the fuel blockade as "an extreme form of unilateral economic coercion" that violates international law.

The Immigration Wild Card

There's a potential trap in Trump's Cuba strategy that could undermine his own domestic agenda. If economic pressure triggers a humanitarian crisis, it could spark another wave of Cuban migration to the US—exactly what Trump has campaigned against.

Cuba has a long history of migration surges during economic crises. The most recent exodus during the pandemic saw nearly 2 million people leave the island. A new crisis could create the kind of immigration emergency that would force Trump to choose between his foreign policy goals and his domestic promises to crack down on immigration and slash government spending.

The 21st Century Reality Check

Trump's "friendly takeover" language harks back to an era when great powers could simply absorb smaller neighbors. But modern geopolitics operates under different rules. Even if Cuba's government were to collapse, a "takeover"—friendly or otherwise—would face massive international opposition and legal challenges.

The more realistic scenario is that Trump's pressure campaign aims to force regime change or at least extract major concessions from Cuba's government. The humanitarian aid and oil licensing policies suggest the administration wants to be seen as offering alternatives to the current leadership while maintaining pressure.