The Trump administration’s top diplomat, Secretary of State Marco Rubio, was overseeing a deal to free several Americans and dozens of political prisoners held in Venezuela in exchange for sending home about 250 Venezuelan migrants the United States had deported to El Salvador.
But the deal never happened.
Part of the reason: President Trump’s envoy to Venezuela was working on his own deal, one with terms that Venezuela deemed more attractive. In exchange for American prisoners, he was offering to allow Chevron to continue its oil operations in Venezuela, a vital source of revenue for its authoritarian government.
The discussions, which included the release of about 80 Venezuelan political prisoners, and the two different deals were described by two U.S. officials and two other people who are familiar with the talks and sought anonymity because of the sensitive nature of the issue.
The State Department never sealed the deal. The top U.S. officials did not appear to be communicating with each other and ended up at cross purposes. The approximately 250 people expelled from the United States are still being held in a maximum-security prison in El Salvador. And it became clear that while Mr. Trump’s White House once said that it had no control over the detainees in El Salvador, it was willing to use them as bargaining chips.
Both U.S. tracks — one managed by Mr. Rubio and the other led by the envoy, Richard Grenell — involved speaking with the same Venezuelan representative, Jorge Rodríguez, the president of Venezuela’s National Assembly, one U.S. official and the two other people said.
The conflicting diplomatic efforts signaled a monthslong divide over how to approach Venezuela and resembled the chaos that permeated Mr. Trump’s first term, when competing officials vied for influence with the president. But the lack of coordination left Venezuelan officials unclear about who spoke for Mr. Trump and, ultimately, left both American and Venezuelan detainees imprisoned.
The offer to swap Venezuelan migrants in El Salvador for prisoners remains on the table, one of the U.S. officials said. The White House is not willing, for now, to extend Chevron’s license in Venezuela.
Mr. Grenell declined an interview request, but said in an email that The New York Times’ reporting about the separate deals was bogus.
A person close to Mr. Grenell who is familiar with the talks with Venezuela said Mr. Grenell did not believe that a swap involving the Venezuelan migrants was going to happen because he believed that Mr. Trump would never have authorized the release of accused gang members. The person spoke on the condition of anonymity to protect the sensitive nature of the ongoing negotiations.
Mr. Trump’s aides said that there was no tension between any of the diplomats.
“There is no fraction or division,” Karoline Leavitt, the White House press secretary, said in a statement. “The president has one team, and everyone knows he is the ultimate decision maker.”
The United States is paying the Salvadoran government millions of dollars to detain migrants who the Trump administration claims are all members of a Venezuelan gang, Tren de Aragua, and who it said had come to the United States to commit crimes.
But the Trump administration has provided little proof that the men are gang members, and their lawyers argue that their detentions are illegal and took place without due process.
The negotiations over the swap, which were led by the State Department and John McNamara, the chargé d’affaires of the U.S. Embassy in Bogotá, Colombia who also oversees Venezuelan affairs, had advanced to the point where in May Venezuela was set to send a state plane to El Salvador to retrieve the men, one of the two people said.
At the same time, the United States planned to send a plane normally used for deportations to Caracas, the Venezuelan capital, to pick up the political prisoners and the Americans. Mr. McNamara planned to fly to Caracas to oversee the handover.
The Venezuelan political prisoners, many of whom were arrested while protesting fraudulent elections held last year, would have been given the choice of staying in Venezuela or going to live in El Salvador, according to one of the people close to the talks.
The swap would have included a range of people who protested the 2024 election results in Venezuela, including a man jailed for criticizing President Nicolás Maduro of Venezuela on TikTok and a former mayor arrested in August.
The detained Americans included Lucas Hunter, who was arrested in January, and Jonathan Pagan Gonzalez, who was arrested last year.
El Salvador’s president, Nayib Bukele, first hinted at such a deal in late April. He suggested on social media that a “humanitarian agreement” would exchange all the Venezuelan migrants for Americans in Venezuelan custody and some Venezuelans. At the time, Venezuelan officials publicly dismissed the proposal and demanded that their “kidnapped” countrymen be returned.
While Mr. Rubio and Mr. McNamara focused on the prisoner swap, Mr. Grenell worked on a deal of his own. Before pitching it to the Venezuelans, Mr. Grenell called the president to tell him about the offer and believed he had the president’s support. But Mr. Grenell had not actually received the president’s final approval, according to one of the U.S. officials.
The White House had already heard from a group of Florida Republicans, Cuban Americans, who threatened not to support Mr. Trump’s tax and domestic policy bill if the administration eased oil sanctions against Venezuela. Mr. Trump’s aides believed that allowing Chevron to export oil from Venezuela would jeopardize Mr. Trump’s domestic policy agenda. Now that the bill has passed, it is unclear if administration officials will change their minds on the Chevron license.
The exchange arranged by the State Department was set to take place in late May. That same month, Mr. Grenell went to Venezuela on a separate mission in which he won the release of Joseph St. Clair, an Air Force veteran held in Venezuela.
Senior Trump administration officials still view Mr. Grenell as a valuable player in the administration, even though some say they believe that he moved too fast — and without the necessary buy-in — in the episode.
Mr. Grenell, the person close to him said, was surprised to learn about the swap, and is the only authorized negotiator on any deals with Venezuela. But since the episode, Mr. Rubio has taken the lead in talking to the Venezuelans, one of the U.S. officials said.
The Venezuelan and Salvadoran governments did not respond with comment.
The relatives of some Americans detained in Venezuela expressed frustration over the failure of the efforts to win their freedom.
“The sense that we parents had was that you had various people talking, but they weren’t working together — one negotiator would say one thing, and another would say something else,” said Petra Castañeda, whose son, Wilbert Castañeda, 37, a Navy SEAL, was arrested last year in Venezuela. “You would think they would be duly coordinated.”
In Mr. Trump’s first term, American officials tried to oust Mr. Maduro through sanctions, diplomatic isolation and the support of an alternative president, a young legislator. Mr. Rubio and other Cuban American Republicans continue to support sanctions and an isolationist approach.
But in the second term, Mr. Grenell has expressed a willingness to work with the Venezuelan government. He made his first trip to Caracas in January, and got several Americans released.
The Maduro government has spent the past year or so rounding up foreigners in its territory and imprisoning them to use in negotiations with foreign governments, according to security analysts and human rights groups.
The Venezuelan watchdog group Foro Penal says there are now 85 people with foreign citizenship wrongfully detained in Venezuela, the largest number the group has ever counted.
While Mr. Grenell was able to secure the release of six Americans in January, and then Mr. St. Clair in May, many more U.S. citizens and permanent residents remained in Venezuelan custody or were recently captured.
The State Department deal that had been in the works with Venezuela included stern warnings that suggested severe consequences if more prisoners were taken after the swap, one of the people said.
Jetzy Arteaga, whose son, Carlos Cañizales Arteaga, has been held in El Salvador since March after migrating to North Carolina, said she was eager to see the deal revived.
“At first, when we heard that our sons were being used as bargaining chips, this offended us a lot,” Ms. Arteaga said. “Our sons are not bargaining chips. But now we realize there is no other option.”
Annie Correal contributed reporting.
Frances Robles is a Times reporter covering Latin America and the Caribbean. She has reported on the region for more than 25 years.
Julie Turkewitz is the Andes Bureau Chief for The Times, based in Bogotá, Colombia, covering Colombia, Venezuela, Bolivia, Ecuador and Peru.
Zolan Kanno-Youngs is a White House correspondent for The Times, covering President Trump and his administration.
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