Politics

Rubio and Trump Envoy Spectacularly Screwed Up Deal to Free American Prisoners

MASTERS OF DIPLOMACY

Two diplomatic teams wound up working at cross-purposes in planned prisoner swap.

Marco Rubio speaks during a North Carolina rally in November, 2024.
Chip Somodevilla/Getty Images

Efforts to free a number of Americans being held in Venezuelan prisons reportedly ended in failure after the Trump administration sent in two separate teams to secure their release.

According to a report in The New York Times, Secretary of State Marco Rubio worked hard to negotiate a deal with the government of Nicolás Maduro to exchange the detained U.S. citizens for roughly 250 Venezuelans who’d been sent to El Salvador as part of President Donald Trump’s nationwide deportation drive.

Meanwhile, Trump’s envoy to Venezuela, Richard Grenell, held separate talks with exactly the same officials to return those same prisoners, but in exchange for allowing U.S. oil company Chevron to continue its operations in the country after its license expired at the end of May, the Times reported.

US President Donald Trump pats Secretary of State Marco Rubio on the shoulder during a cabinet meeting in the Cabinet Room of the White House in Washington, DC, on July 8, 2025. (Photo by ANDREW CABALLERO-REYNOLDS / AFP) (Photo by ANDREW CABALLERO-REYNOLDS/AFP via Getty Images)
Earlier this year, Secretary of State Marco Rubio had worked to negotiate the exchange of U.S. citizens held in Venezuela for Venezuelan prisoners deported from the U.S. to El Salvador. ANDREW CABALLERO-REYNOLDS/AFP via Getty Images

Neither deal happened—leaving both sets of prisoners still in their cells, and Venezuelan officials bewildered as to who exactly among the two teams of U.S. diplomats was supposed to have been negotiating on Trump’s behalf.

Grenell flat-out denied to the newspaper he had engaged in separate talks with Maduro’s authoritarian government. A source with knowledge of those negotiations apparently said Grenell had held them because he didn’t believe Trump would be willing to release migrants he’s accused, in many cases without proof, of being violent gang members.

Trump appointed Richard Grenell as the Kennedy Center's interim executive director.
Meanwhile, Trump's envoy to Venezuela, Richard Grenell, was working on a separate set of talks, ultimately resulting in both deals falling through. Chip Somodevilla/Getty Images

Before making his proposal to the Venezuelan administration, the newspaper further reports Grenell in fact called Trump to discuss it with him. He came away from that conversation under the impression he had the president’s backing, even though sources say Trump had still not given final approval.

As the Trump administration’s envoy to Venezuela, the diplomat was apparently surprised to hear Rubio’s department had been involved in negotiating with Maduro’s officials. Since the deal, or deals, fell through, however, the secretary of state has reportedly taken charge of future talks with the Venezuelan government.

“There is no fraction or division,” White House Press Secretary Karoline Leavitt told the NYT in a statement. “The president has one team, and everyone knows he is the ultimate decision maker.”

The Daily Beast has reached out to the White House, the State Department, Richard Grenell, and the U.S. Embassy in Bogota, which was involved in the first set of negotiations, for comment on this story.

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