The CIA’s Cuba Ultimatum: Regime Change With a Diplomatic Smile

create the crisis, punish the population, scare off investment, then demand political surrender from the government you have spent decades trying to brea. – — force Cuba to bend to Washington’s will.

SCHEERPOST, May 19, 2026.

The CIA did not sneak into Havana this time. It landed in broad daylight.

Peter Kornbluh reports in The Nation that CIA Director John Ratcliffe led a high-level U.S. delegation to Cuba on May 14, delivering what amounted to a blunt Trump administration ultimatum: Washington is willing to “engage” on economic and security issues, but only if Cuba makes “fundamental changes.”

The message is hard to miss. After decades of sabotage, sanctions, assassination plots, covert operations and economic strangulation, the U.S. is now packaging regime-change pressure as diplomacy. Cuba is facing severe fuel shortages, blackouts and growing hardship — conditions Washington’s policy has helped intensify — while Trump officials tighten sanctions, target foreign investors and float military threats.

This is not diplomacy. It is submission politics.

Kornbluh’s piece lays out the old imperial script in its newest form: create the crisis, punish the population, scare off investment, then demand political surrender from the government you have spent decades trying to break. The CIA’s public trip to Havana may look different from Bay of Pigs secrecy or Operation Mongoose sabotage, but the goal remains painfully familiar — force Cuba to bend to Washington’s will.

The danger now is that economic warfare is being paired with open military signaling. Reports of increased U.S. intelligence flights near Cuba, threats involving aircraft carriers, possible indictments of Cuban leaders and leaked claims about Cuban drones all point toward a familiar pretext-building machine.

Once again, the United States claims to be defending freedom while tightening the noose around an island it has never forgiven for refusing to obey.

The CIA has spent decades trying to overthrow the Cuban government through covert operations, assassination plots, sabotage, and economic warfare — from the Bay of Pigs to Operation Mongoose and countless regime-change schemes. But now Washington isn’t even pretending anymore. CIA Director John Ratcliffe’s very public trip to Havana marks a dangerous new phase in the long U.S. campaign to force Cuba into submission politically and economically.

According to reports, Ratcliffe delivered what was essentially a “do or die” ultimatum from the Trump administration: either Cuba accepts Washington’s demands for change, or the window for diplomacy closes. He reportedly pointed to what happened in Venezuela after Maduro refused to bend to Trump’s threats, making clear the White House is prepared to “enforce its red lines” if Cuba refuses to capitulate.

The timing says everything. Ratcliffe arrived just one day after Cuba publicly admitted the country has effectively run out of fuel. “We have absolutely no fuel oil, and absolutely no diesel,” Cuba’s energy minister said on state television. That crisis didn’t happen in a vacuum. Cutting off Cuba’s access to fuel, electricity, and basic economic survival has become central to Trump’s pressure campaign against the island.

As one analyst put it, previous administrations tried to lure Cuba with carrots. Trump’s strategy is to beat Cuba with a stick until it collapses. And with U.S. military activity escalating around the region, it’s becoming harder to ignore the possibility that Washington is preparing for something even more dangerous if Cuba refuses to surrender to its imperial demands.

Read The CIA Goes to Cuba from Peter Kornbluh at The Nation