Trump's Three-Nation Regime Change Gambit Eyes Cuba Next

In 70 years, no American president has dared attempt what Donald Trump is now pursuing: the simultaneous toppling of three autocracies that have tormented generations of US leaders. With Nicolás Maduro in a New York courtroom and Iran's Ayatollah Khamenei dead from missile strikes, Trump has set his sights on the final piece of his geopolitical puzzle—Cuba, just 90 miles from Florida.

"The president is feeling like, 'I'm on a roll'; like, 'This is working,'" one administration official revealed. Trump has openly floated the possibility of a "friendly takeover" of the island nation of 11 million people, with Secretary of State Marco Rubio conducting "very high level" discussions with Cuban leaders.

The Legacy Play: Beyond Reagan and Nixon

Behind Trump's public Cuba musings lies something deeply personal, according to administration officials and confidants. The president sees himself as the first modern American leader with the courage to complete what others merely flirted with—map-changing transformations that could cement his legacy above Ronald Reagan (who bested the Soviet Union), Jimmy Carter (who secured the Camp David Accords), and Richard Nixon (who restored relations with China).

This represents a remarkable pivot from the isolationist rhetoric that defined his three presidential campaigns and first term. Trump is now pursuing an unprecedented trio of regime changes in countries that have long vexed American foreign policy.

Iran fell into Trump's crosshairs due to its nuclear ambitions and threats to US service members. Venezuela and Cuba fit into the administration's goal of solidifying Western Hemisphere dominance—an objective that now includes threats to annex Greenland, seize the Panama Canal, and make Canada the 51st state.

The Confidence of Success, The Risk of Overreach

Trump has repeatedly emphasized Cuba's dire economic state, telling reporters "there's no oil, there's no money, there's no anything." He argues that the post-Castro regime is so fundamentally weak that its own rot would inevitably do the work of an invading army.

The administration has already escalated pressure dramatically. Trump declared a national emergency over Cuba's hosting of Russian intelligence facilities and authorized punitive tariffs on any country supplying oil to Havana. US forces have begun intercepting vessels en route to Cuba, while maintaining a strict blockade.

But the risks are enormous. A destabilized Cuba could trigger a refugee crisis just as the administration tries to reverse immigration flows. After nearly seven decades of repressive rule, there's little organized opposition to lead any transition to democracy.

Historical Echoes and Modern Dangers

Presidential historian Timothy Naftali sees parallels to December 2001, when the ease of overthrowing the Taliban in Afghanistan emboldened the George W. Bush administration to target Saddam Hussein. "He had been a boil on the backside of American foreign policy and in the wake of 9/11, the country's willingness to tolerate threat was low, and its ambitions to make the world a safer place were high."

Every US president except Barack Obama has pursued Cuba's downfall through various means—from Reagan's terrorism designation and sanctions to Bill Clinton's covert democracy programs. Even the CIA's more creative attempts included exploding mollusks for Fidel Castro's underwater excursions and poison-filled cigars (abandoned when Castro quit smoking in the 1980s).

None worked. Castro died of natural causes in 2016 at age 90, having successfully transferred power to his brother Raúl a decade earlier.

The Venezuela Model: Success or Illusion?

The dramatic seizure of Maduro demonstrated Trump's willingness to pursue regime change. Venezuela has remained relatively calm since Trump decided to work with Maduro's vice president, Delcy Rodríguez. Political prisoners have been released, and the Venezuelan economy has stabilized through US-arranged oil sales.

But the Trump administration has offered no timeline for democratic transition. Simply removing Maduro may satisfy Trump's ambitions—a model that could apply to Cuba, where regime change might mean working with existing power structures rather than democratization.

The Military Reality Check

What could go wrong with forceful action? "Oh my God," Naftali warns. "What could go wrong is what could go wrong in Iran. When you have a police state populated by people who have no future in a pro-American successor government, they have no incentive to give up, and they have the monopoly on firepower."

The US military is already stretched from the Caribbean to the Persian Gulf. "No one has used open military operations since the Bay of Pigs," notes William LeoGrande, co-author of "Back Channel to Cuba," adding with dark humor, "and that didn't go very well."

Unlike Venezuela's narco-trafficking charges or Iran's nuclear threats, Cuba lacks a clear legal predicate for military action. The terrorism designation that justifies current sanctions appears "nonsensical" upon close examination, according to LeoGrande.