WASHINGTON (States Newsroom) — A federal judge Friday probed the U.S. Department of Justice about whether the Trump administration knowingly defied his court order to return deportation flights to the United States and questioned the president’s authority to invoke a wartime law during peacetime.
The case, which is likely to head to the U.S. Supreme Court, will test President Donald Trump’s authority to invoke the Alien Enemies Act of 1798 and apply it to any Venezuelan nationals ages 14 and up who are suspected members of the Tren de Aragua gang amid his mass deportation plans.
Three deportation flights containing some Venezuelans subject to the proclamation that Trump signed last Friday were in transit when U.S. District Court Judge James Emanuel Boasberg issued a temporary restraining order to block the removals. But the administration continued sending the men to a notorious mega-prison in El Salvador.
The Trump administration published a highly produced video detailing the operation, but has not been forthright with answers to questions Boasberg posed about it.
“The government’s not being terribly cooperative at this point, but I will get to the bottom of whether they violated my order, who ordered this and what the consequences will be,” Boasberg said Friday.
Wartime law
Boasberg also pressed the Department of Justice attorney Drew Ensign on whether the Trump administration can deport people under the Alien Enemies Act without allowing the deportees to prove they are not members or associated with the Tren de Aragua gang.
“How do they challenge that removal?” Boasberg asked.
The Alien Enemies Act allows nationals of a country deemed an enemy of the U.S. to be detained and deported without due process of law regardless of immigration status.
Boasberg also raised concerns of using the proclamation when the U.S. is not at war.
“The policy ramifications for this are incredibly troublesome,” Boasberg said of the Alien Enemies Act. “This is a long way from the heartland of the act.”
A panel of judges in the U.S. Court of Appeals for the District of Columbia Circuit will hear oral arguments Monday afternoon on the Trump administration seeking an emergency stay on the restraining order.
Restraining order
Boasberg asked DOJ attorney Ensign to clarify how he interpreted the oral temporary restraining order issued on March 15.
He asked Ensign if he relayed to the Trump administration that his order included returning any Venezuelans back to the U.S. who were deported under the wartime authority.
“I understood your intent, that you meant that to be effective at that time,” Ensign said of the oral temporary restraining order.
In filings, the Department of Justice has argued that Boasberg’s oral argument was not binding because it was not written.
For nearly a week, the Department of Justice has evaded pointed questions from Boasberg about the timing of the deportation flights on March 15.
Boasberg said Thursday he would give the Trump administration until Tuesday to submit a declaration on whether the government was invoking the state-secrets privilege and a brief “showing cause why they did not violate the Court’s Temporary Restraining Orders by failing to return class members removed from the United States on the two earliest planes that departed on March 15, 2025.”
In Friday filings, Trump officials said they are currently having Cabinet-level conversations about using that privilege to block Boasberg from obtaining details about the timing of the deportation flights.
Flight location an issue
The Department of Justice has also argued that because the flights were no longer in U.S. airspace or territory when Boasberg issued the restraining order, they were not under U.S. courts’ jurisdiction.
Lead attorney for the American Civil Liberties Union Lee Gelernt pushed back on that claim. He told Boasberg that some immigrants on those deportation flights to El Salvador were returned to the U.S. because of mistakes and that the El Salvadoran “government would not take them.”
He said that included someone who was not a Venezuelan national, and a woman because the mega-prison is for men only.
He said the ACLU will submit an affidavit late Friday with more details.
Gelernt said the ACLU is also questioning the type of removal for people on the third flight, even though the Trump administration said those on that flight had final orders of removal and were not subject to the Alien Enemies Act.
Gelernt argued that in immigration law, those with final orders are required to be notified what country they are being deported to. He said that was not the case with the immigrants on the third flight, which originally went to Honduras before heading to El Salvador.
“We asked the judge to clarify that with the government, because it seems very doubtful that Venezuelans had a final order that said you could be removed to El Salvador,” Gelernt said to reporters after Friday’s hearing.
The White House earlier this week said of the men on the deportation flights, 137 were alleged Tren de Aragua members and deported under the Alien Enemies Act.
Attorneys for several of the 238 Venezuelan men deported argue their clients are not members of the gang and were only targeted by immigration officials because they had tattoos and were Venezuelan nationals.
El Salvador prison
Gelernt said that because the Trump administration is paying the government of El Salvador $6 million to imprison the men, he believes those men who were deported under the wartime law can be returned, although it would be a lengthy process.
“I think we very much think the federal court can order the U.S. to get them out, since they’re constructively in U.S. custody,” he said outside the courtroom. “The U.S. is apparently paying for it all. (El Salvador is) doing it at the behest of the United States.”
Human Rights Watch, a nonprofit that monitors human rights conditions around the world, has raised major concerns with the conditions of the prison and has noted that the group “is not aware of any detainees who have been released from that prison.”
Nicolás Maduro, Venezuela’s authoritarian president, called this week for the men taken to the mega prison to be returned to Venezuela, calling on El Salvador president to “not be an accomplice to this kidnapping, because our boys did not commit any crime in the United States, none,” according to CNN.
“They were not brought to trial, they were not given the right to a defense, the right to due process, they were deceived, handcuffed, put on a plane, kidnapped, and sent to a concentration camp in El Salvador,” Maduro said.
Several of the men who were transferred to El Salvador’s prison initially fled Venezuela because they experienced violence from officials after they partook in political protests against the Maduro regime, according to court filings.
