The Russian Oil Tanker Playing Chicken With Trump Over Cuba

The Anatoly Kolodkin is steaming toward the Caribbean.

The Russian oil tanker’s official destination, according to one of its public broadcasts: “Atlantis, USA.” More probably, it’s the Cuban port of Matanzas.

Ferrying an estimated 730,000 barrels of crude oil across the Atlantic, the tanker is flying a Russian flag. A Russian warship escorted it through the English Channel, where it was tracked by the Royal Navy for 48 hours, only to turn back as soon as the tanker was clear.

While the Kremlin declined to confirm reports of Russian oil heading to Cuba, it also has made little effort to conceal its hand.

That’s because the tanker was never really about Cuba at all, people close to the White House, former ambassadors and Russia observers told POLITICO. It’s a message, they said — a negotiating chit, a provocation designed to force a disproportionate American response while Washington is consumed elsewhere.

“Russia loves to poke us in the eye,” Lawrence Gumbiner, who led the U.S. Embassy in Havana during President Donald Trump's first term, said in an interview. Russia, he said, isn’t “serious about coming to Cuba’s rescue.”

“It’s not in their interest to pick a fight with Trump over something that is so, so clearly within the U.S. orbit as Trump has defined it,” Gumbiner said — a reference to Trump’s so-called “Donroe Doctrine” to assert U.S. dominance in the Western Hemisphere and diminish the influence of adversaries like Russia and China.

The Kolodkin could arrive in Cuba in the next two or three days, according to Michelle Wiese Bockmann, a senior maritime intelligence analyst at Windward AI. Its ostensible goal: delivering much-needed oil to the communist island, which has been under a U.S. economic blockade for months as Trump threatens to take it over.

There’s also a second vessel, the Hong Kong-flagged Sea Horse, believed to be carrying roughly 200,000 barrels of Russian diesel. It was headed toward Cuba in February before stopping short and drifting at sea for three weeks before recently resuming course, diverting toward Venezuela.

The Treasury Department made clear last week the oil embargo on Cuba stands, even as it moved to ease sanctions on other countries purchasing Russian oil, an attempt to mitigate surging energy prices triggered by the war in Iran. The standoff comes as global oil markets are already rattled by the war in Iran, which has sent energy prices surging and forced the administration into the awkward position of temporarily easing Russian oil sanctions to stabilize supply, even as it tries to choke off Cuba.

Former Trump officials told Playbook the U.S Navy and Coast Guard are likely to intercept the Kolodkin before it reaches port — but the White House isn’t yet tipping its hand.

“Cuba is a failing nation whose rulers have had a major setback with the loss of support from Venezuela,” said a White House official, granted anonymity to speak candidly.

Russia’s test of U.S. commitment in the Western Hemisphere comes as Washington already battles the Kremlin’s influence on two other fronts: over intelligence sharing with Iran, and the ongoing war in Ukraine. My colleagues reported over the weekend that Moscow proposed a quid pro quo to Trump’s favored envoys Steve Witkoff and Jared Kushner — stop sharing intelligence with Ukraine, and Russia would stop sharing coordinates of U.S. military assets in the Middle East with Iran. The U.S. rejected the proposal.

While the attempt to provide oil to Cuba may be half-hearted in the face of significant U.S. maritime opposition, Russia watchers say the signal it sends is not.

“Even though the Trump administration has prioritized Latin America, the Russians are signaling that they're not willing to fully give that up until — or, I should say — unless the United States makes significant concessions for Ukraine and gives up Russia’s backyard,” said Andrea Kendall-Taylor, a longtime senior U.S. intelligence official, now senior fellow and director of the Transatlantic Security Program at the Center for a New American Security.

Her sharpest assessment, though, lands closer to home: “Putin is demonstrating that he can ruthlessly prioritize his foreign policy and national security. I'm not sure we can say the same thing for prioritization on the U.S. side.”

Not everyone reads it that way. Alex Gray, who served as National Security Council chief of staff during the first Trump administration, sees the tanker as the desperate move of a weakening state — and expects the administration to treat it as such.

“He likes to push as far as he can until someone calls his bluff,” Gray said of Putin. “At the cost of one oil tanker, they can try and create a disproportionate impact on our focus and resources.”

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