Trump Eyes Cuba: US-Russia Standoff Looms Over Oil & Regime Change

Trump’s Cuba Plan: A High-Stakes Gamble in the Atlantic

A Russian oil tanker is creeping west across the Atlantic, quite possibly toward a confrontation with the United States Navy.

The Anatoly Kolodkin is carrying an estimated 730,000 barrels of crude oil apparently meant for Cuba, which is battling a fuel shortage. But it may not reach its destination: The U.S. Navy is policing the Caribbean to choke off Havana’s oil supply. The tanker is owned by the Russian state-run shipping company Sovcomflot and is under sanctions from the United States, the European Union and the United Kingdom.

The Trump administration is squeezing Cuba to a breaking point—and is seemingly willing to engage in a high-seas stand-off that has pronounced Cold War echoes. Donald Trump’s goal appears to be to install more amenable leadership in Havana. Last week, he told reporters at the White House that he believes he’ll have the “honor of taking Cuba,” adding: “Whether I free it, grab it—I think I can do anything I want with it.”

The White House is calculating that the island’s extreme economic hardships will provide the leverage Trump needs to force Havana into submission. Cuba’s president, Miguel Díaz-Canel, publicly acknowledged discussions between the two governments last week and pledged a series of reforms aimed at appeasing Washington, a concession that indicated both the urgency of the domestic crisis and the vulnerability of the regime. Cuba’s economy, already hollowed out by mismanagement, communist economic ideology, sanctions, and the end of subsidized oil from Venezuela, is now tormented by island-wide blackouts and food shortages. After the COVID-19 pandemic, more than 1 million people left the island—about 10 percent of Cuba’s population. Another wave could be coming if the island doesn’t receive economic relief.

The government-to-government talks hold the potential for a peaceful settlement—but the track record isn’t strong. U.S. Discussions with the regimes in Iran and Venezuela in recent months came to naught, prompting military intervention in both countries. Officials said the U.S. Approach to Cuba would likely replicate the course of events in Venezuela—and that the switch from negotiation to military action could happen imminently.

Preparing for Intervention

The U.S. Attorney’s office in South Florida is preparing indictments against Cuba’s political and military leadership—including members of the Castro family—on a range of possible charges related to alleged violent crime, drug-trafficking, immigration, and espionage, four people familiar with the planning told reporters on condition of anonymity. (The U.S. Used a 2020 indictment against Venezuela’s president, Nicolás Maduro, as a predicate for his capture.) The State Department has long accused the Cuban regime of human-rights violations, including alleged arbitrary or unlawful killings, torture, degradation of political prisoners, and repression of journalists. Cuba denies the accusations.

Administration officials are also discussing which wealthy Republican donors with Cuban ancestry could be considered for future transition or leadership roles in Havana.

“Regime change is lined up,” one administration official said. But Trump-style regime change is unlikely to be the democratic uprising that many Cuban exiles have longed for. Venezuela is expected to be the model. The administration found that its short-term goals of ousting a repressive dictator and opening opportunities for U.S. Companies was best met by empowering Maduro’s deputy, Delcy Rodríguez, who proved more willing to engage with Washington. Much of the Caracas regime remains in place.

Trump’s approach is: “We control our hemisphere, and we have the ability to do this,” one person familiar with the planning said. “We want these hostile regimes out of our hemisphere, and we’re going to set up the business community, because we don’t believe in diplomacy.”

Cuba’s Crisis Deepens

In Cuba, signs of severe strain are everywhere. Cities such as Havana and Santiago de Cuba effectively disappear in the night from blackouts. Stockpiles of hospital supplies, gas, and other basics are dwindling. Water distribution is disrupted because pumps have stopped running. Uncollected garbage piles up on city streets because trash trucks lack fuel. Experts warn that the island’s economic contraction has pushed Cuba into its most perilous state since the dissolution of the Soviet Union, its former economic sponsor and political protector.

The United Nations has warned of a potential “collapse” if fuel shortages persist, noting rising food prices, failing agricultural production, and widespread power outages. Citizens wait hours for gasoline; businesses are closed for lack of electricity; and state-guaranteed benefits—health care, food distribution—have eroded. China has offered renewable-energy equipment, expertise, and financing to ease the crisis, but how swiftly it can scale-up this effort is unclear.

“An island that was once the crown jewel of the Caribbean has plunged into extreme poverty and darkness,” the State Department said in a statement. “This is the tragic result of over sixty years of Communist rule.”

Influential Cuban American donors and activists in Florida are pressing the Trump administration to seize the opportunity to overthrow the regime. But some Cubans still revere the 1959 revolution, and, as one foreign official said, have no desire to humiliate Raúl Castro (Fidel’s 94-year-old brother and a former president), or even Díaz-Canel, who is widely viewed as a weak bureaucrat. “They just want life to improve,” the official said.

Trump is less fixated on regime change or forcing an ideological shift away from communism than on securing broad U.S. Latitude to invest, develop, and ultimately capitalize on Cuba’s underdeveloped cities and beaches, people familiar with his thinking said.

Trump has sought opportunity in Cuba since his real-estate days. In October 2008, he applied for a trademark in Cuba, according to records from the Cuban Industrial Property Office. The application was approved in March 2010 and was active until its expiration in 2018. Trump held discussions on financial opportunities in Cuba with administration officials and Trump Organization staff during his first term in the White House. One person who met with Trump at the time said that the president had been most excited about the prospect of Trump-branded hotels or condominiums. “He’s interested in Cuba as a market for him, and completely agnostic about the politics,” this person said. “He didn’t care.”

That is at odds with the views of Secretary of State Marco Rubio, who has long called for the toppling of the regime. Rubio said Cuba needed “fresh people in charge” but didn’t say the government had to go.

The Role of GAESA and Potential Successors

Rubio has privately focused his attention on economic reforms—particularly on dismantling the Grupo de Administración Empresarial S.A., the largest conglomerate in Cuba, known as GAESA. Controlled by the Cuban military, GAESA operates a portfolio of enterprises that constitutes 40 to 70 percent of the Cuban economy.

Manuel Marrero Cruz, the current prime minister, is among the leaders Washington could potentially work with. The Communist Party devotee is also viewed as a pragmatic technocrat by some in Washington. Deputy Prime Minister Óscar Pérez-Oliva Fraga, a great-nephew of Fidel and Raúl Castro, is another potential successor, though less likely, some said. Fraga told NBC News last week that Cuba was open to a “fluid commercial relationship” with American companies.

The talks between the two governments center on American demands for a change in leadership, restitution for owners of property seized by the Cuban government, and the opening of investment and commerce.

“We are talking to Cuba, whose leaders want to make a deal and should make a deal, which President Trump believes would be remarkably easily made,” Anna Kelly, a White House spokesperson, said in a statement. “Cuba is a failing nation whose rulers have had a major setback with the loss of support from Venezuela.”

But the discussions could turn out to be, in part, a form of subterfuge, one person familiar with the talks said, much as they were with Venezuela. The U.S. Could claim that Cuba has refused to budge on some key condition as a predicate for a military-backed law-enforcement action.

Cuba appears aware of the threat: Its diplomats and intermediaries have been seeking meetings with U.S. Think tanks, academics, and journalists in an effort to influence U.S. Opinion and buy time to prepare for a possible conflict, several people familiar with the outreach said. U.S. Officials, meanwhile, are discussing how best to engage with the American and international business communities, and with religious organizations, to drum up support for U.S. Intervention.

A Delicate Moment

Any action against Cuba would come at a moment of high stress for the Trump administration amid the intense war with Iran. Before initiating hostilities in Venezuela and Iran, the U.S. Military spent weeks building up naval and air assets. That has yet to happen near the shores of Cuba, in part because the Navy has been stretched by those other conflicts.

In the past, before going to war with Iran, any White House would have worried about how the Kremlin might respond. Weighed down by the financial and military cost of its war with Ukraine, Russia has stayed on the sidelines. But, perhaps sensing an opportunity to needle Washington in its own hemisphere, Moscow dispatched two tankers toward the Caribbean, laden with oil that is under U.S. Sanctions. “This is the showdown,” one Trump administration official said with a sense of dread.

The U.S. Appeared to provide an opening when the Treasury Department earlier this month lifted sanctions for 30 days on some Russian energy shipments in a bid to stabilize global energy prices. But a week later, the Treasury Department amended the terms to exclude transactions with a handful of countries, including Cuba. Samir Madani, a co-founder of TankerTrackers.com, a maritime-intelligence firm, said one of the tankers appears to have been redirected toward Venezuela. But the Anatoly Kolodkin is plowing ahead.

The situation remains fluid and fraught with risk. The arrival of the Russian tankers, coupled with the Trump administration’s aggressive posture, sets the stage for a potentially dangerous confrontation in the Caribbean.