Exclusive: Trump's accelerating squeeze on Cuba

• "The best way to describe it is 'accelerationism,' " one senior administration official said, referring to the philosophy of hastening societal collapse.
• "But we don't want to kill off the regime just yet. There's a method to this. It's in stages."

Zoom in: This methodical squeezing of Cuba's communist regime is also designed to buy time for Trump — who's now engrossed in peace talks with Iran — to eventually focus on Cuba and decide how to bring about change there.

• "Iran's not finished, and the president is not in a rush," said another senior administration official. "Trump wants to exhaust all the levers that he can. But at this point, there aren't as many levers as before."
• Said a third senior administration official: "We have a pretty deep toolbox, especially when it comes to sanctions and enforcing them. More is on the way."

The big picture: The Cuba operation aims to eliminate Latin America's source of Marxist agitation and anti-U.S. activism ever since Fidel and Raul Castro led their successful revolution in 1959.

• To bring Cuba to its knees this year, the administration first focused on the island's lifeline: Venezuela and its socialist leader, Nicolas Maduro, who kept Havana afloat with shipments of oil that helped power the country and gave it a source of export revenue.

• Maduro, who'd been indicted in the U.S. on "narco-terrorism" charges in 2020, was seized in a daring U.S. raid Jan. 3. After that, Venezuela's free oil shipments stopped, plunging Cuba into a new economic crisis.
• The U.S. blames Cuba for its economic woes. Cuba blames the U.S.

Inside the room: Last month, U.S. Southern Command, which oversees military operations in the Caribbean, held a multiagency "tabletop" exercise to prepare for military action in Cuba, one of the senior U.S. officials said.

• "Everything is on the table, but no invasion is planned or imminent," the official said. "When POTUS says go, we're ready for anything."

In the exercise, another source said, U.S. officials discussed Cuba's possession of drones and how to respond to possible unrest in the sweltering Cuban heat as spring turns to summer.

• During the July 11, 2022, uprisings on the island, Cuban authorities brutally repressed and imprisoned demonstrators demanding more freedoms. Now circumstances are worse.
• "It's going to be hot. People won't have electricity. Food spoils without refrigeration. People get angry. They can take to the streets. And then what happens? I can't see the president doing nothing if there's repression," that source said.
• But another source, a Trump adviser, disagreed: "The president does not want boots on the ground for more than 48 hours. It's a quagmire in the making. This could get messy."

Zoom out: One presidential adviser said the approach to Cuba is "classic Trump: Push your enemy off balance. It's pressure, watch the response, apply more pressure, watch the response, apply more pressure."

• On May 1, Trump signed an executive order imposing "secondary sanctions" targeting companies, many of them foreign, from doing business with the mammoth Cuban military-industrial umbrella organization known as GAESA.
• The order led Canadian mining company Sheritt International and the shipping companies CMA CGM and Hapag-Lloyd to suspend their Cuba operations. Financial institutions and hotel companies in countries such as Spain, Panama and Mexico are expected to pull out of Cuba as well.
• These sanctions differ from the U.S. embargo, which essentially prohibits trade with the island and has existed in one form or another since 1962.
• "We've never seen this kind of pressure," said Max Meizlish, an ex-Treasury official who specialized in Cuba sanctions. "It's an entirely new ballgame."

Between the lines: Secretary of State Marco Rubio is a chief architect of Trump's Latin America policy and has led the administration's messaging against GAESA. He announced GAESA sanctions on May 7 and made it the centerpiece of a May 20 Cuban Independence Day video message to the island's citizens.

• That day, the Justice Department unsealed a federal murder indictment of Raul Castro for allegedly ordering the 1996 Brothers to the Rescue shootdowns. And SOUTHCOM announced the arrival of the Nimitz Carrier Strike group in the region.
• On May 21, Rubio announced the arrest of the sister of the woman running GAESA after he terminated her green card.

• Two days later, Fox News reported that Treasury officials were examining leftist streamer Hasan Piker and the activist group Code Pink for potentially violating U.S. sanctions during a March trip to Cuba.

State of play: Castro's indictment led to comparisons with the Maduro regime-change operation, but Trump officials and advisers say there are three crucial differences:

1. The U.S. has not identified, nor has Trump picked, Cuban officials who could run an interim government in Havana if the current regime collapses.

• In contrast, Trump had decided Maduro could be safely replaced by Venezuela's vice president, Delcy Rodriguez, well before the Jan. 3 raid in Caracas.
• "The problem is not that there's no Delcy in Cuba. There could be Delcy Lites or people who are Delcy-ish. But there's no greenlight from [Trump] to really engage yet," said one official.

2. Seizing Castro in the same way Maduro was abducted wouldn't lead Cuba to a dramatic reorientation toward the U.S. because the Castros 30 years ago began transitioning away from one-man rule.

• "The problem with that decentralization, it breeds lack of decision-making and lots of incompetence," the official said.

3. The Cuban embargo is also codified in U.S. law and can be undone only if the island frees political prisoners, has free elections and guarantees other civil rights. That limits Trump from normalizing relations with a new government by executive fiat as he did in Venezuela, whose sanctions had been imposed by the U.S. executive branch.

• "The problem is that Congress has a say," the official said, noting that Miami's three Cuban-American congressional representatives have hardline positions on Cuba that reflect South Florida's conservative exile community.

The Cuba policy is not all sticks. There are carrots as well.

• The U.S. this month announced it's giving $100 million in assistance to Cuba, provided it's not sent to the government and flows instead through the Catholic Church and other charities. It offered $6 million to Cuba after Hurricane Melissa last year.
• "If we wanted to hasten the collapse, we would not have sent any assistance," said senior administration official who described U.S. policy as a "campaign to show people they can have a better life if the regime got out of their way."
• Cuba's foreign minister, Bruno Rodriguez Parrilla, told Fox News on Sunday that the U.S., and Rubio specifically, are manipulating public opinion to justify military intervention.

The bottom line: "The politics are complicated on both sides [of the Strait of Florida]," one of the officials said.

• "But we have time. The regime doesn't."