American Civil Liberties Union lead attorney Lee Gelernt holds a press conference outside the U.S. District Court for the District of Columbia after a March 21, 2025, hearing on deportation flights that occurred despite a court’s restraining order in place. (Photo by Ariana Figueroa/States Newsroom) 

WASHINGTON — 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. 

U.S. Attorney General Pam Bondi testifies before the Senate Judiciary Committee during her confirmation hearing on Jan. 15, 2025. (Photo by Chip Somodevilla/Getty Images)

WASHINGTON — The U.S. Department of Justice on Tuesday refused to provide further details about deportation flights that were in flight when a federal judge issued an order blocking the invocation of the wartime law used to authorize the removals.

In new court filings, the Department of Justice said two deportation flights to El Salvador and Honduras were not subject to a restraining order from U.S. District Court Judge James Emanuel Boasberg because they were no longer in U.S. territory or airspace when the order was issued.

In a notice signed by Attorney General Pam Bondi, the Justice Department would not answer further questions about those flights, contradicting Boasberg’s order late Monday calling for the administration to answer four specific questions about details of the operation.

“The Government maintains that there is no justification to order the provision of additional information, and that doing so would be inappropriate, because even accepting Plaintiffs’ account of the facts, there was no violation of the Court’s written order (since the relevant flights left U.S. airspace, and so their occupants were ‘removed,’ before the order issued), and the Court’s earlier oral statements were not independently enforceable as injunctions,” according to the notice.

“The Government stands on those arguments.”

In response to the filing, Boasberg issued a new order, giving the administration until noon Eastern on Wednesday to give those details under seal.

Specifically, he is asking what times the flights took off from the United States, when they left U.S. airspace, when they landed in their designated countries, when those immigrants being deported were subject to the Alien Enemies Act and the number of people on the flights who were subject to the Alien Enemies Act.

The Department of Justice has also argued that an oral order given by Boasberg was “not enforceable” because it was not a written order.

Fighting the judicial order

In a temporary restraining order barring President Donald Trump from invoking the Alien Enemies Act of 1798 to detain and deport any Venezuelan nationals 14 and older who are suspected members of the Tren de Aragua gang, Boasberg also ordered those flights carrying Venezuelan men to return to the U.S. Those men instead were taken to a maximum security prison in El Salvador.

Boasberg on Monday demanded sworn statements from the Department of Justice to determine if the Trump administration relied on the Alien Enemies Act to deport any of the Venezuelan men flown to El Salvador, which would have violated his Saturday temporary restraining order.

In the Tuesday notice signed by Bondi, the Department of Justice also argued that “the Government should not be required to disclose sensitive information bearing on national security and foreign relations.”

Another hearing before Boasberg is set for Friday afternoon.

Authority for deportations

Robert Cerna, the acting field office director for enforcement and removal operations for U.S. Immigration and Customs Enforcement, said in a signed statement to the court that the immigrants on a third deportation flight after the Saturday restraining order were not removed under the Alien Enemies Act, but under a separate final removal authority known as Title 8.

“To avoid any doubt, no one on any flight departing the United States after 7:25 PM EDT on March 15, 2025, was removed solely on the basis of the Proclamation at issue,” he said.

Boasberg issued his temporary restraining order Saturday around 6:48 p.m. Eastern, according to court filings. One of the flights landed in Honduras at 7:36 p.m. Eastern and the other flight landed in El Salvador at 8:02 p.m. Eastern.

Cerna also clarified that the president signed the proclamation invoking the wartime law on Friday, but that ICE understood the proclamation went into effect after the White House published it Saturday afternoon.

Cerna said there are roughly 258 additional immigrants who would be subject to the proclamation. Of those people, Cerna said that 54 were already detained.

18th-century law

The Alien Enemies Act has only been invoked three times, all when the U.S. was at war with other countries. The most recent was during World War II, when it led to the rapid detention and internment camps of nationals from Japan, Italy and Germany.

The U.S. is not at war with another country, and Congress has not approved a declaration of war. The Trump administration has argued that by designating the Tren de Aragua gang as a terrorist group, the act can be invoked.

The White House has defended the deportation flights and has argued that it has not violated the court’s order.

White House press secretary Karoline Leavitt said during a Monday press briefing that the Trump administration is confident it will be successful in court.

She added that the U.S. paid El Salvador $6 million to detain the 261 men who were deported to the country.

Appeals

The president has lashed out against the temporary restraining order, even calling for the impeachment of Boasberg, along with other federal judges who have ruled against his administration.

“This judge, like many of the Crooked Judges’ I am forced to appear before, should be IMPEACHED!!! WE DON’T WANT VICIOUS, VIOLENT, AND DEMENTED CRIMINALS, MANY OF THEM DERANGED MURDERERS, IN OUR COUNTRY. MAKE AMERICA GREAT AGAIN!!!,” Trump wrote on social media.

It prompted a rare statement of rebuke from U.S. Supreme Court Chief Justice John G. Roberts.

“For more than two centuries, it has been established that impeachment is not an appropriate response to disagreement concerning a judicial decision,” Roberts said. “The normal appellate review process exists for that purpose.”

The Trump administration has already appealed the temporary restraining order to the D.C. Circuit Court of Appeals.

In that appeal, the Justice Department asked the appellate court to remove the case from Boasberg, taking issue with his decision to agree to a class action lawsuit, rather than apply the restraining order to the original five men in the suit.

The American Civil Liberties Union originally brought the suit with five men who are Venezuelan and were threatened “with imminent removal under” the Alien Enemies Act.

The case is likely to head to the U.S. Supreme Court.