As they addressed reporters inside the Oval Office in mid-April, President Trump and his Salvadoran counterpart appeared to be operating in lock step.
The United States had just deported more than 200 migrants to a maximum-security prison in El Salvador, and President Nayib Bukele said his country was eager to take more. He scoffed at a question from a reporter about whether he would release one of the men who a federal judge said had been mistakenly deported.
“I mean, we’re not very fond of releasing terrorists into our country,” Mr. Bukele said.
But weeks earlier, when the three planes of deportees landed, it was the Salvadoran president who had quietly expressed concerns.
As part of the agreement with the Trump administration, Mr. Bukele had agreed to house only what he called “convicted criminals” in the prison. However, many of the Venezuelan men labeled gang members and terrorists by the U.S. government had not been tried in court.
Mr. Bukele wanted assurances from the United States that each of those locked up in the prison were members of Tren de Aragua, the transnational gang with roots in Venezuela, according to people familiar with the situation and documents obtained by The New York Times.
The matter was urgent, a senior U.S. official warned his colleagues shortly after the deportations, kicking off a scramble to get the Salvadorans whatever evidence they could.
Mr. Bukele’s demands for more information about some of the deportees, which has not been previously reported, deepen questions about whether the Trump administration sufficiently assessed who it dispatched to a foreign prison.
The New York Times pieced together the most complete account yet of the U.S. arrangement with El Salvador and the March 15 deportations from internal government documents, court filings and interviews with 22 people familiar with the operation or legal challenges, many of whom spoke on the condition of anonymity to avoid retaliation.
For months, aides to Mr. Trump had worked to engineer a new system to deport immigrants rapidly to Central and South America, with little to no oversight from the courts. The strategy hinged on using an 18th-century wartime law and treating the migrants like citizens of a country at war with the United States.
But the application of the rarely used Alien Enemies Act appeared to be haphazard, pulling in migrants whose relatives insisted they were not gang members. Government officials hurried to assemble documents detailing who was sent to the prison and justify the deportations in court. The process was so messy that eight women were among those flown to be incarcerated in the Salvadoran prison, an all-male facility, and had to be swiftly returned.
Friends and families of the men locked up in El Salvador are now struggling to extract information about their fate. The White House is in a standoff with the federal courts over how it has applied the Alien Enemies Act, with the Supreme Court expected to weigh in soon, a potentially significant test of Mr. Trump’s attempts to expand his executive power.
“The president has the right to remove foreign terrorists from our homeland, and we are absolutely confident that truth will ultimately prevail in court,” the White House press secretary, Karoline Leavitt, said in a statement. “In the meantime, the administration continues to comply with all court orders.”
El Salvador’s prison, called the Terrorism Confinement Center, gave Mr. Trump a fearsome symbol to underscore his determination to execute mass deportations, as well as a facility outside of the reach of American lawyers and the accountability of the U.S. legal system.
In Mr. Bukele, the White House had a willing ally, albeit one with specific demands, including a list of high-ranking MS-13 gang leaders he wanted sent back to El Salvador as part of the deal.
That stoked alarm among some U.S. law enforcement officials. The Justice Department has spent years building cases against MS-13 leaders for criminal activities in the United States, alleging that the gang has been protected by the Salvadoran government.
A spokeswoman for Mr. Bukele, who has denied those claims, did not respond to requests for comment.
Secretary of State Marco Rubio, who said he worked directly with the government of El Salvador “to deport as many dangerous gang members illegally in America as possible,” is now looking for other foreign partners, as well.
“I intend to continue to try and identify other countries willing to accept and jail as many gang members as we can send them,” Mr. Rubio said in a statement.
Stephen Miller, the main architect of Mr. Trump’s domestic agenda, had a message for other advisers inside the presidential transition offices in West Palm Beach, Fla.: Be bold. Do not worry about potential litigation, especially when drafting Mr. Trump’s immigration actions.
It was roughly a month before the inauguration, and Mr. Miller knew he needed to move fast to make good on Mr. Trump’s campaign pledge of mass deportations.
Mr. Miller had long been interested in the Alien Enemies Act, a law passed in 1798 that allows the U.S. government to swiftly deport citizens of an invading nation. The authority has been invoked just three times in the past, all during times of war. He saw it as a powerful weapon to apply to immigration enforcement.
The law “allows you to instantaneously remove any noncitizen foreigner from an invading country, aged 14 or older,” Mr. Miller told the right-wing podcaster Charlie Kirk in a September 2023 interview, adding: “That allows you to suspend the due process that normally applies to a removal proceeding.”
Venezuelans had arrived in the United States in record numbers over the previous several years, following the collapse of their economy under the government of President Nicolás Maduro. Venezuelan migrants crossed the border more than 760,000 times during the Biden administration, according to the nonpartisan Migration Policy Institute. Many had pending asylum cases.
The surge had included Neri José Alvarado, a onetime college student from Yaracuy, Venezuela, who traveled through the Darién jungle and crossed the U.S.-Mexico border illegally in April 2024, hoping to find work and pay for the medical care of his younger brother, who has autism.
He got a job working at a bakery in the Dallas area while waiting for his bid for asylum to be considered. In the application he filed to U.S. officials, Mr. Alvarado said he dreamed of becoming a “great psychologist.” He also said that he feared returning to Venezuela because he had participated in protests against the Maduro government.
In his home country, he wrote in his application, “I am afraid of being in a country where constitutional guarantees are not respected.”
In Mr. Trump’s telling, the incoming Venezuelans were primarily gang members and psychopaths. At rally after rally, he claimed without evidence that members of Tren de Aragua had crossed the border en masse and taken over American communities.
His team knew they wanted to use the wartime authority to accelerate deportations. But they also needed a place to send the Venezuelan immigrants, whose government was not regularly accepting deportation flights from the United States.
Early on, Trump advisers identified El Salvador as a promising option. Mr. Bukele, who has called himself the world’s “coolest dictator,” had come into office pledging to crack down on gang crime. Matt Gaetz, who late last year resigned from Congress and was Mr. Trump’s initial pick to lead the Justice Department, visited Mr. Bukele last July and toured his new Terrorism Confinement Center, known as CECOT, a sprawling facility with eight cell blocks that each holds 3,000 prisoners.
Mr. Bukele was willing to let the United States use his prisons — with conditions, he told Mr. Rubio and Mauricio Claver-Carone, Mr. Trump’s Latin American envoy.
He did not want to bring in noncriminal migrants; he could not convince Salvadorans he was prioritizing their national interests if he turned their country into a dumping ground for U.S. deportees from other countries, he explained to Mr. Trump’s aides.
But he did agree to take in violent criminals, no matter their nationality, for a fee, which would help subsidize the country’s prison system.
Mr. Bukele had his own request: a list of MS-13 leaders that he wanted released from U.S. custody and sent to El Salvador, where he said they could be interrogated by his security officers.
Some U.S. law enforcement officials were alarmed over the prospect of sending back leaders of MS-13 now facing charges for alleged crimes in the United States. Both the Treasury Department and Justice Department have accused Mr. Bukele’s government of making a secret pact with MS-13, offering its leaders behind bars special privileges to keep homicides down in El Salvador. Mr. Bukele has denied the claims.
“What Bukele is desperate for is to get these guys back in El Salvador before they talk in U.S. court,” said Douglas Farah, an El Salvador expert who between 2018 and 2022 collaborated with the Justice Department “Vulcan” task force, which targeted MS-13, as a U.S. military contractor.
Nevertheless, U.S. officials agreed to send El Salvador around a dozen senior members of MS-13, including a high-ranking leader named César Humberto López-Larios, who had been in U.S. custody awaiting trial on narco-terrorism conspiracy charges. Mr. Bukele has so far not received everyone he sought, but U.S. officials say they still intend to send additional gang leaders he has requested.
For Mr. Trump and his aides, the unconventional swap — getting a foreign country to take a group of Venezuelans migrants, along with Salvadoran-born MS-13 members — was a bargain price to pull off the kind of deportations they sought, even with the millions the United States agreed to pay to house the Venezuelans.
The Plan Unfolds
Early this year, Mr. Alvarado, the Venezuelan asylum seeker, was settling into his new life outside Dallas. The 25-year-old got a promotion at the bakery, from assistant to lead baker, and was sending money home to cover his brother’s doctor appointments.
“He was a kid who helped his family a lot,” said his boss, Enrique Hernández. “Neri is a young man without a bad bone in his body.”
And Mr. Alvarado finally had a date and time for his asylum hearing: Feb. 13, at 1 p.m.
On Feb. 4, Mr. Alvarado was getting into his car outside his apartment building to head to work when three vehicles carrying ICE agents pulled up, he later told Mr. Hernández. They told him he was being detained for illegally entering the United States. Mr. Alvarado responded that he was in the process of seeking asylum and had a hearing in days, he told his boss.
They detained him anyway. On the way to the Bluebonnet Detention Facility in northern Texas, the agents quizzed him about his tattoos, Mr. Alvarado later told his sister, Izaida Alvarado. Mr. Alvarado explained the tattoo on his leg, a rainbow ribbon made of puzzle pieces, was for his autistic brother.
That same week, thousands of miles away in El Salvador, Mr. Rubio and Mr. Bukele discussed the deportation deal and took a stroll around the grounds of the presidential residence. Mr. Bukele teased the plan to accept “convicted criminals” from the United States, calling it a “no brainer” to work with the United States.
Detained inside Bluebonnet, Mr. Alvarado missed his Feb. 13 asylum hearing, and was told that he would be deported as a result, his sister said. He could appeal, but he was exhausted, he told his family, and ready to give up on the United States and return to Venezuela.
Mr. Alvarado was among many migrants detained in the weeks between Mr. Trump’s inauguration and mid-March later sent to the prison in El Salvador — picked up outside of their homes, in their neighborhoods, or in raids, traffic stops and appearances at their regular ICE check-ins. Some had already been in asylum proceedings or had a form of legal status. Immigration officials zeroed in on Venezuelan men who had tattoos, citing markings such as crowns and clocks as evidence that they were members of Tren de Aragua.
Others also got caught up in the dragnet.
On March 12, federal immigration agents pulled over Kilmar Armando Abrego Garcia as he was driving through College Park, Md., with his 5-year-old son. Mr. Abrego Garcia had come to the United States illegally in 2012 from El Salvador at age 16, fleeing gang violence, according to his attorneys. In 2019, an immigration judge had determined he should not be deported back to El Salvador because he might face danger there.
Now, officers were ordering him out of his car, saying his immigration status had changed. The administration would later argue that Mr. Abrego Garcia was a member of the MS-13 gang, a claim that a federal judge would say was questionable.
The next day in Texas, Lindsay Toczylowksi, an immigration attorney, found that her client, a 31-year-old Venezuelan makeup artist named Andry Hernández Romero, did not appear in court at an expected hearing. Ms. Toczylowski was not initially alarmed.
“It sort of felt like we were in the realm of normal immigration chaos,” she said.
It was not the usual chaos. The administration was already accelerating plans for the El Salvador operation, an effort that would sweep up her client and more than 200 others.
On March 14, the Trump administration exchanged diplomatic notes with El Salvador laying out the terms: Mr. Bukele’s government would receive up to 300 members of Tren de Aragua in exchange for financial support from the United States.
That same day, Mr. Trump hinted at the forthcoming deportations during a speech at the Justice Department. Sitting in the front of the audience was Mr. Miller, who had moments earlier conferred with Todd Blanche, the deputy attorney general, about the pending deportations.
“We’ve caught hundreds of them, the Venezuelan gang, which is as bad as it gets,” Mr. Trump told a crowd of loyalists. “And you’ll be reading a lot of stories tomorrow about what we’ve done with them and you’ll be very impressed.”
That day, Mr. Trump secretly signed an executive order declaring that Tren de Aragua was “conducting irregular warfare” at the direction of Venezuela. He called for the apprehension and removal of all Venezuelans aged 14 and older who were deemed members of the gang, formally invoking the Alien Enemies Act. It was the first time it had been invoked by a U.S. president since World War II, when it was used to justify the internment of people of Japanese, Italian and German nationality or ancestry.
The administration would not make Mr. Trump’s proclamation public until the next day, something immigration lawyers would later argue was a deliberate effort to avoid a quick legal challenge.
By then, ICE had transferred dozens of Venezuelan men detained around the country to facilities in Texas to prepare for the operation. Many thought they were headed back home.
From detention, Mr. Alvarado called his family and told them to prepare for his arrival in Venezuela. So did Gustavo Adolfo Aguilera Agüero, 27, another Venezuelan who entered the United States through a Biden-era program before he was picked up by ICE when Mr. Trump came into office.
“Have patience, vieja, we are going to be together soon,” Mr. Aguilera told his mother using a term of endearment, she later recalled. “The planes are here.”
In the Air
Judge James E. Boasberg opened the virtual hearing late on the afternoon of Saturday, March 15, by apologizing for his attire: a dark sweater, rather than his judicial robe.
“I went away for the weekend and brought with me neither a robe nor tie nor appropriate shirt,” he said.
The judge had hastily gathered lawyers for the Justice Department and the American Civil Liberties Union to consider an emergency petition filed early that morning by the liberal advocacy group, seeking to stop the deportation of five Venezuelans under the Alien Enemies Act.
Judge Boasberg had quickly paused their deportations, and was considering whether his order should extend to all Venezuelan migrants.
He pressed the government: Were there any deportation flights set to take off for El Salvador in the next two days?
“We can certainly investigate that and report that back to you,” said Drew Ensign, a Justice Department lawyer.
The judge adjourned the hearing for roughly 40 minutes so that Mr. Ensign could learn more. But when the group reassembled, Mr. Ensign said he could not share any details, citing potential national security issues.
Shortly before 7 p.m., Judge Boasberg extended his order to cover all migrants who might fall subject to Mr. Trump’s proclamation invoking the Alien Enemies Act. Any plane en route with deportees needed to turn around, he said.
“Whether turning around a plane or not embarking anyone on the plane or those people covered by this on the plane, I leave to you,” Judge Boasberg said. “But this is something that you need to make sure is complied with immediately.”
What Judge Boasberg did not know at the time was that two flights carrying Venezuelan migrants had taken off from Texas while the hearing was in recess, according to public databases.
They were in the air when Judge Boasberg issued his order from the bench. A third plane was still on the ground in Texas.
In all, there were more than 260 people on the three aircraft, including 238 Venezuelans and nearly two dozen alleged MS-13 gang members. They were headed to El Salvador.
Inside the White House, senior administration officials quickly discussed the order and whether they should move ahead. The team of Trump advisers decided to go forward, believing the planes were safely in international airspace, and well aware that the legal fight was most likely destined for the Supreme Court, where conservatives have a majority.
At 7:36 p.m., the third flight took off. Officials would later say the migrants on that flight were not deported under the Alien Enemies Act, but through regular immigration proceedings.
The White House’s decision to press forward, despite Judge Boasberg’s order, raised questions about whether the administration was defying the court. The Justice Department has argued that a federal judge cannot dictate foreign policy.
In Venezuela, Miriam Aguilera Agüero had been waiting up, wondering where her son was. It was not until her daughter-in-law sent her images of the Venezuelan deportees in El Salvador posted on social media that she recognized him. Her heart dropped. The image showed dozens of prisoners in white T-shirts and shorts sitting cross-legged, their hands cuffed and heads down. One detainee stood out for his awkward sitting position.
Ms. Aguilera’s son had to sit like that, she said, given the damaged discs in his spine.
Disappeared
In Washington, the Trump administration was working to address Mr. Bukele’s confusion about who the United States had sent him. Eight women who had been mistakenly sent were swiftly flown back.
The Salvadoran president wanted to confirm that all of the Venezuelans were actually members of Tren de Aragua. Any regular deportees were to be held separately in his prison.
Publicly, the administration insisted all 238 Venezuelans who were deported were members of Tren de Aragua. But few had documented public links to the gang and officials admitted that many did not have criminal records in the United States. “The lack of specific information about each individual actually highlights the risk they pose,” Robert L. Cerna, a top deportation official, wrote in a court filing.
To determine their gang affiliation, the Homeland Security Department had created a scorecard in which the men were assigned points for different categories. A broad range of tattoos were worth four points. A tally of eight points was considered evidence of gang membership.
State Department officials said they provided El Salvador with the scorecard and other intelligence showing the Venezuelans were Tren de Aragua members.
Still, inside the U.S. government, some career staff had qualms about what had unfolded.
During an internal State Department briefing about issues related to Latin America, some employees were dismayed to hear that weeks earlier, American spy agencies had assessed that Tren de Aragua was not actually controlled by the Venezuelan government — which was the premise for invoking the Alien Enemies Act.
On Capitol Hill, Democratic lawmakers tried to find out more about how much El Salvador was being paid to imprison the deportees, a figure that administration officials now say amounted to less than $5 million. On March 17, the State Department told the Senate Appropriations Committee that sum could grow to $15 million, but refused to provide any additional details.
Then scrutiny by the federal courts deepened, exactly the scenario the administration had been trying to avoid. The Supreme Court ruled that the Venezuelans need to have a meaningful chance to challenge their deportations, and the court is expected to weigh in further on the use of the Alien Enemies Act.
In public posts and comments to reporters, Mr. Trump has made his displeasure clear: The courts needed to get out of the way.
“We’re going to have a very dangerous country,” Mr. Trump said in the Oval Office, “if we’re not allowed to do what we’re entitled to do.”
For the relatives and lawyers of the imprisoned men, who have struggled to get information about them from U.S. and Salvadoran authorities, the courts are their last recourse.
Mr. Hernández, the bakery owner who had employed Mr. Alvarado, went to an ICE office to try to find out what had happened to his employee, but got no answers. He has considered flying to El Salvador to try to negotiate his freedom.
Mr. Hernández, a U.S. citizen who emigrated to the United States from Venezuela 27 years ago, called the actions of his adopted country “a crime.”
“They didn’t investigate him,” he said. “They took him and they didn’t even know who he was.”
Zolan Kanno-Youngs, Hamed Aleaziz, Alan Feuer, Devlin Barrett and Jonathan Swan reported from Washington. Julie Turkewitz reported from Bogotá, Colombia, Maggie Haberman from New York and Annie Correal from Mexico City. Reporting was contributed by Natalie Kitroeff, Jazmine Ulloa, William K. Rashbaum, Robert Jimison, Maria Abi-Habib and Isayen Herrera.
