As Secretary of State Marco Rubio spoke of the “incredible opportunities” to partner with Vladimir Putin’s Russia if a peace deal to end his invasion of Ukraine is achieved, the Russian leader was sending hundreds of thousands of oil barrels to Cuba, offering a lifeline to a regime Rubio, a Cuban American from Florida, had just recently called “an enemy of humanity.”

A Russian tanker carrying 790,000 barrels valued at $55 million arrived in Havana last week, a reminder of Putin’s geopolitical ambitions in the Western Hemisphere. The shipment will help keep the regime in Havana afloat at a critical time, while also undermining a recent tightening of sanctions that Rubio’s State Department touted as a return to a tough Cuba policy.

The parallel developments pose questions about how Rubio, who had called Putin “a war criminal” and had blasted Cuba for supporting him, will navigate what looks like a disjointed Trump administration’s foreign policy and his long-standing opposition to authoritarian regimes in Cuba, Russia, Venezuela and elsewhere.

Rubio’s first month has been packed with high-profile negotiations about the wars in Ukraine and Gaza, a Latin American tour that yielded commitments to help the administration’s immigration agenda, high-level meetings with European allies and the fallout of a controversial slashing of foreign-aid funds.

At times, that has meant he’s had to accommodate or stay silent about actions taken by the Trump administration that appear to go against his deep-rooted beliefs and fiery comments he has made on democracy and human rights while in the U.S. Senate and on social media.

Rubio had commented on the inevitability of a negotiation to end the war in Ukraine and more recently had voted against the $95 billion in U.S. aid to the country in April 2024. But the image of Rubio meeting Russian foreign minister Sergei Lavrov in Saudi Arabia and his later remarks about engaging to identify “the extraordinary opportunities… the incredible opportunities that exist to partner with the Russians, geopolitically on issues of common interest, and frankly economically,” marked a notable contrast to his days in the Senate, when he sponsored several bills supporting Ukraine and seeking to impose sanctions on Putin’s Russia.

“The world will become a very scary place if we allow thugs like Putin to invade sovereign nations without severe consequence,” he said when he introduced a bill in 2022 to sanction Moscow-backed separatists controlling Ukraine territory in 2022. “We must be clear and unyielding in our support for the Ukrainian people’s fight against a merciless tyrant, and that begins with calling his actions for what they are — an act of terrorism.”

Ahead of the Russian invasion of Ukraine, Rubio sought to impose personal sanctions on Putin and other Russian officials. That year alone, he and other senators introduced the Non-Recognition of Russian Annexation of Ukrainian Territory Act, along with bills to ban the imports of Russian agricultural products and U.S. investments in Russian securities. He also joined a bipartisan resolution calling for the investigation of Putin for war crimes.

Rubio is also the author of the bill that renamed the street where the Russian embassy in Washington is located to “Boris Nemtsov Plaza,” in honor of the slain Russian dissident.

“He is in a very difficult position because his long-held beliefs are not the ones he has been tasked to defend now,” a former U.S. diplomat said about Rubio’s current position. “He has always been for freedom.”

The former official, who asked not to be identified to candidly discuss Rubio’s predicament, called President Donald Trump’s alignment with Putin in recent remarks in which he falsely blamed Ukraine for starting the war and called its president, Volodymyr Zelenskyy, a dictator, “shameful.”

“Trump doesn’t understand that Russia is not our friend. The dictator in this picture is Putin, who is a war criminal,” the former diplomat said.

The State Department did not reply to a request for comment for this story.

In an interview with journalist Catherine Herridge, Rubio smoothed over Trump’s comments about Zelenskyy and played down the significance of his first meeting with the Russian officials.

But foreign policy observers believe Trump’s remarks will also make it harder for Rubio to call out Venezuela’s strongman, Nicolas Maduro, or Cuba’s handpicked president, Miguel Diaz-Canel, both strong Russian allies in Latin America.

The Venezuela case, in particular, the former diplomat said, was a good example of what he sees as a White House that does not seem to coordinate its actions or messages, risking alienating Hispanic voters in South Florida.

As Rubio was about to embark on his first trip as secretary of state — a tour of five Latin American and Caribbean nations to highlight the importance of the region for the new administration — the White House sent special envoy Richard Grennel to negotiate a deal with Maduro — who is wanted in the U.S. on “narco-terrorism” charges — to accept more Venezuelan deportees, stunning Venezuelan exiles who had enthusiastically embraced Trump.

When top Biden administration officials had met Maduro in Caracas in 2022 to negotiate to resume oil imports from Venezuela, Rubio, at the time a senator, called the move a “treason” to the Venezuelan opposition, saying in a Spanish video that Maduro had hoped for Joe Biden to get into the White House, because he knew that “eventually, he would get into an arrangement with him.”

Now, as secretary of state, Rubio — who had to briefly delay his trip to Latin America after learning of Grenell’s plans, according to the former diplomat who spoke to the Herald — was put in the position of having to deny on a Fox News interview that the U.S. was recognizing Maduro as the legitimate head of the Venezuelan government.

Just a week before Grenell’s trip, Rubio had spoken to Edmundo Gonzalez, the opposition candidate widely believed to have won the latest presidential election in July, and he called him “the rightful president of Venezuela.”

During a Harvard University event this week, Juan Gonzalez, the former State Department head of Western Hemisphere affairs under Biden, said the recent events signal “a divergence” between how the State Department and the White House will address the Venezuela issue. Others have warned that the episode suggests Trump’s White House is not as committed to the defense of democracy and human rights as Rubio.

“I don’t think democracy as such is in the Trump agenda anywhere with regard to Venezuela,’ said Carolina Jiménez Sandoval, president of the human-rights group Washington Office on Latin America, in a seminar about the future of U.S. relations with the region organized by the David Rockefeller Center for Latin America Studies.

“I think we are very likely going to be seeing tension between the State Department and the White House, and that tension will remain unresolved,” she said, noting that the White House also canceled temporary protections against deportation for thousands of Venezuelans in the United States. “What I see right now is a strong connection between the Venezuela opposition and the State Department under Marco Rubio” — but not policymakers at the White House, she added.

The controversy surrounding the foreign-aid freeze order affecting USAID programs and other international assistance has also put Rubio in the position of having to defend the cuts while trying to salvage humanitarian programs. Rubio, who has been named acting director of USAID, said he had issued a blanket waiver to reauthorize emergency humanitarian support. Still, the programs have yet to receive the funds because the payment system has been taken offline under what sources said are orders by Peter Marocco, the director of the State’s Office of Foreign Assistance and deputy administrator-designate at USAID.

Particularly frustrating to people in Miami is that Rubio has let the freeze order suspend funds going to several organizations run by Cuban, Venezuelan and Nicaraguan exiles to support the restoration of democracy in those countries.

“The word dictator means something to us,” said another former U.S. official. “It’s sad because we are on the same team, but how is the State Department canceling those contracts and Marco letting that happen?”

The Venezuela mishap and other incidents — like Trump’s threats of “taking back” the Panama Canal just hours after Rubio sought to patch things over during his visit to that country — stem from the administration’s seeming disarray and Trump’s authoritarian manner, the former U.S. diplomat said.

“Nobody is coordinating or thinking of the consequences,” the former U.S. official said. “The Biden administration was a complete disaster, but no one was expecting this disorganization. I feel bad for Rubio. He can be a good secretary of state. He is very smart, but he is being undermined.”

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