Seized Tanker Reveals Cuba’s Secret Oil Lifeline As Trump Turns To Gunboat Diplomacy

Secretary of State Marco Rubio has realized that it is all about following the money. If the U.S. military posture in the Caribbean is one of “gunboat diplomacy” aimed at ushering in regime change in Caracas, Venezuela’s capital, against the country’s autocratic leader, Nicolás Maduro, then one way to accelerate regime instability is to weaken Cuba materially.

During President Trump’s first term, there was a brief moment in which the Maduro regime appeared close to being overthrown, but it was countered by support from Cuba. According to The New York Times reporters Michael Crowley and Edward Wong, that failure frustrated Trump, his advisers, and then Senator Rubio, who had backed regime change.

“Their theory of change involves cutting off all support to Cuba,” said Juan S. Gonzalez, who was President Joe Biden’s top White House aide for Western Hemisphere affairs. “Under this approach, once Venezuela goes, Cuba will follow.”

In a separate NYT report, journalists Anatoly Kurmanaev, Nicholas Nehamas, and Farnaz Fassihi explained that the seized tanker Skipper, which was carrying crude contracted by Cubametales, Cuba’s state-run oil trading firm, is a critical part of how Cuba benefits from its oil trade with Venezuela.

The reporters cited internal data from Venezuela’s state oil company, PDVSA, showing that Skipper’s destination was listed as the Cuban port of Matanzas.

They continued:

Two days after its departure, Skipper offloaded a small fraction of its oil, an estimated 50,000 barrels, to another ship, called Neptune 6, which then headed north toward Cuba, according to the shipping data firm Kpler. After the transfer, Skipper headed east, toward Asia, with the vast majority of its oil on board, according to a U.S. official briefed on the matter.

President Nicolás Maduro of Venezuela and his predecessor, Hugo Chávez, have for decades sent oil to Cuba at highly subsidized prices, providing a crucial resource at low cost to the impoverished island.

In return, the Cuban government over the years has sent tens of thousands of medics, sports instructors, and, increasingly, security professionals on assignments to Venezuela. That exchange has assumed special importance as Mr. Maduro has leaned on Cuban bodyguards and counterintelligence officers to protect himself against the U.S. military buildup in the Caribbean.

In recent years, however, only a fraction of Venezuelan oil set aside for Cuba has actually reached the island, according to PDVSA documents and tanker tracking data. Most of the oil allocated for Cuba has instead been resold to China, with the money providing badly needed hard currency for the Cuban government, according to multiple people close to the Venezuelan government.

And noted Panamanian businessman Ramón Carretero is at the center of the Venezuela-Cuba oil flow:

The main person managing the flow of oil between Cuba and Venezuela is a Panamanian businessman named Ramón Carretero, who in the past few years has become one of the largest traders of Venezuelan oil, according to PDVSA data and people close to Venezuela’s government.

The U.S. Treasury Department imposed sanctions on Mr. Carretero on Thursday for “facilitating shipments of petroleum products on behalf of the Venezuelan government.” Mr. Carretero, through a legal representative, declined to comment on the government’s decision. He did not respond to detailed questions for this article.

Mr. Carretero’s role as an economic intermediary between Cuba and Venezuela was first reported by Armando.info, a Venezuelan investigative news outlet.

Skipper was also part of Iran’s dark tanker fleet:

Before shipping Venezuelan oil, Skipper spent four years as part of Iran’s covert fleet, transporting Iranian oil to Syria and China, according to data from Kpler, the shipping data firm, and a senior Iranian oil ministry official, who discussed sensitive issues on condition of anonymity.

What’s likely happening is that the Trump administration is in the early innings of disrupting large volumes of crude that flow from Venezuela to Cuba to China. That strategy could trigger falling dominoes across the region, pushing Cuba’s economy deeper into collapse while also meaningfully weakening Venezuela and tipping the balance of power away from Maduro.

So far, Beijing has yet to lash out over the Skipper seizure and the resulting disruptions to crude flows to Asia. One has to wonder whether Bessent worked out a secret deal with Beijing; otherwise, this type of maneuvering by the Trump administration risks triggering turmoil that could derail any upcoming Trump-Xi talks.