by Ariana Figueroa, Kentucky Lantern
April 3, 2025

WASHINGTON — Judge James E. Boasberg on Thursday strongly implied there was probable cause that the Trump administration violated his orders over deportation flights carried out under the Alien Enemies Act of 1798.

“It seems to me … that the government acted in bad faith throughout that day,” he said of March 15, when the administration sent three flights of Venezuelan nationals to a notorious El Salvador mega-prison and seemingly defied his order to return them.

“If you believed everything you did was legal, I can’t believe you would have operated the way you did that day,” Boasberg said to Drew Ensign, a deputy assistant attorney general who is representing the administration in the case.

An order of contempt could come as soon as next week, Boasberg said. He said if he finds the government in contempt, there would be hearings to determine the official, or officials, who defied his order and the possible consequences of those actions.

Contempt would allow Boasberg to issue a fine against certain officials in order to force compliance or he even could order U.S. marshals to jail an official.

During Thursday’s hearing, Boasberg questioned why the proclamation was signed “in secret,” noting it was put into use before a judge could review it.

“Is there any other inference (than) that there was an expedited effort to get people on planes…before my hearing,” Boasberg asked, referring to a March 15 hearing that ended with the judge placing the temporary restraining order blocking the use of the law.

For more than an hour Thursday, Boasberg grilled Ensign about the timing of three deportation flights after the wartime law was invoked.

In the order, Boasberg also required the return of any mid-air flights to the U.S.

But rather than return the flights, the government delivered more than 261 men to a notorious mega-prison in El Salvador known as CECOT. 

Boasberg questioned Ensign on which government officials were aware his temporary restraining order was in place and asked for the name of the person who decided not to turn the flights around.

Ensign said he was not sure and then cited attorney-client privileges, which Boasberg seemed skeptical about. Ensign then said he was not aware of who made the decision to not turn the flights around.

The Trump administration has denied it violated any orders and has said that it followed the law.

Contempt hearings possible

Boasberg asked American Civil Liberties Union attorney Lee Gelernt what process for a contempt finding they would recommend.

Gelernt said having the government write sworn declarations answering pointed questions and having officials questioned under oath would be acceptable steps.

“We feel the order was violated,” Gelernt said. 

ACLU has already filed for a preliminary injunction while the case proceeds.

In the motion for a preliminary injunction, ACLU argued that the Trump administration’s use of the Alien Enemies Act violates administrative and immigration laws and constitutional rights to due process.

“Plaintiffs will suffer severe and irreparable harm in the absence of a preliminary injunction, as demonstrated by class members who have already been removed and consigned to a life sentence in a Salvadoran prison without … notice or the opportunity to contest the government’s designation,” according to the brief.

A hearing for a preliminary injunction is set for April 8.

The Trump administration on March 28 made an emergency appeal to the U.S. Supreme Court to allow for deportations under the wartime law – something that until now, had only been used during wars: the War of 1812, World War I and World War II. A decision from the high court is expected soon.

Seeking information

President Donald Trump has publicly attacked Boasberg, calling for his impeachment. The Justice Department has also tried to have Boasberg removed from the case.

Attorney General Pam Bondi invoked the “state secrets privilege” late last month to refuse to answer Boasberg’s detailed questions about the flights.

Boasberg rejected that argument in Thursday’s hearing, asking Ensign if the information was classified.

Ensign said it was not classified.

Boasberg then questioned why the Trump administration refused to show him the information he was seeking, as is common in cases with sensitive information such as national security details.

There are specific rooms called Sensitive Compartmented Information Facility, or SCIFs, where sensitive information can be discussed with officials, such as a federal judge.

Boasberg said the administration was acting “pretty sketchily” in not showing him the information. 

In various hearings, Boasberg has expressed doubt that the Trump administration can use the wartime law to deport Venezuelans accused of gang ties without due process. Boasberg has agreed that the president has broad authority over foreign policy and deportations, but has deemed deportations can’t be done without due process.

Aside from determining if the Trump administration violated his restraining order with the deportation flights, Boasberg is trying to determine if the president violated the Alien Enemies Act by deporting Venezuelans without proper judicial review.

Department of Justice attorneys have argued that those subject to the Alien Enemies Act do not need to be notified. Instead, they argue anyone subject to the proclamation who wants to challenge it can make a habeas corpus claim – that is, challenge the legality of their detentions.

Flights to El Salvador

At issue are three deportation planes that eventually went to the prison in El Salvador on March 15. Two of the planes left before Boasberg gave a verbal order to pause deportations under the Alien Enemies Act.

One plane left after Boasberg issued a written order, but the Trump administration has said those on the third flight had removal orders under Title 8, not the wartime law.

Ensign said the proclamation was signed on March 14, but didn’t go into effect until the next day.

Boasberg questioned how U.S. Immigration and Customs Enforcement was able to have enough time to load up three planes and deport Venezuelans under the proclamation if they only knew about it that day.

Ensign conceded that ICE likely was preparing for the proclamation ahead of time.

“If that’s true, one could infer, they were working on the proclamation before it was public,” Boasberg said.

Boasberg also noted public comments the president made, where Trump said he wasn’t sure who signed the proclamation or when it was signed.

Ensign said he had not seen the press conference during which the president made those remarks.

Deportation errors

Boasberg questioned Ensign about who was notified when he first placed the temporary restraining order. Ensign stuttered and seemed uncomfortable, and said he could not remember. Boasberg gave him time to recall.

Ensign listed off members of his DOJ team and points of contact at the State Department and the U.S. Department of Homeland Security.

Boasberg again noted the “rushed” nature of the flights and how the government has erred in deporting people, including a Maryland father who originally from El Salvador who was sent to prison due to what ICE and DOJ have called an “administrative error.”

Boasberg also noted that eight women and one Nicaraguan national were returned from the March 15 flights because the prison was only for men and El Salvador was only taking Venezuelans and their own nationals.

Boasberg asked Ensign why the Trump administration would “risk putting people on these planes that should not be on (the) planes.”

Ensign said he didn’t have specific operational details.

Family members and attorneys for many of the men have disputed the Trump administration’s claims that those taken to El Salvador were members of the Tren de Aragua. They claim the men were deported because ICE agents misinterpreted their tattoos. Many deportees had no criminal record and were in asylum hearings before an immigration judge, they added. 

Last updated 8:04 p.m., Apr. 3, 2025

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