U.S. District Judge James Boasberg expressed serious concerns on Thursday regarding whether the Trump administration violated a court order that blocked deportations under the 1798 Alien Enemies Act. This raised the possibility of contempt proceedings against the administration.

The case centers on the administration’s use of the Alien Enemies Act to deport Venezuelan nationals, including suspected members of the violent Tren de Aragua gang. During the hearing, Judge Boasberg pressed Deputy Assistant Attorney General Drew Ensign on why the government appeared to disregard an emergency injunction issued last month that halted these deportations. Although the administration has appealed the case to the Supreme Court, Boasberg is currently evaluating whether there is enough evidence to pursue contempt charges, with a decision expected as early as next week.

Boasberg questioned Ensign about who within the Trump administration was aware of the deportation flights and the timing of the three planes that departed U.S. soil for El Salvador. On the day in question, at least 261 migrants were deported, including over 100 Venezuelan nationals removed “solely on the basis” of the law that had been temporarily blocked by the court.

“You maintain that the government was in full compliance with the court’s order on March 15, correct?” Boasberg asked. Ensign affirmed this, prompting the judge to respond, “It seems to me the government acted in bad faith that day.” Boasberg further asserted, “If you really believed everything you did that day was legal and would survive a court challenge, you would not have operated the way that you did.”

The judge also pressed Ensign about whether any materials related to the deportation flights were classified, which could invoke state secrets protections. Government attorneys had declined to provide details about the flights in court, citing national security concerns. However, Ensign suggested that the flight information was likely not classified, leading Boasberg to question why it had not been shared with him in a private, ex parte briefing.

“Can you think of one instance where the state secrets privilege was invoked using unclassified info?” Boasberg asked, to which Ensign struggled to respond. The judge remarked, “Pretty sketchy,” in response to the situation.

Another focal point of the hearing was the timeline of events, particularly when President Trump signed the proclamation authorizing the use of the Alien Enemies Act and when federal agents began boarding migrants onto planes bound for El Salvador. Boasberg noted that the administration started loading the planes on the morning of March 15, several hours before the flights took off.

“So then it’s not crazy to infer there was prior knowledge and actions ahead of the Saturday night deportations?” he asked Ensign. The judge demanded specifics about who was aware of the deportations, including names, locations, and the agencies involved, as well as any internal discussions with other administration officials monitoring the court proceedings.

“Who did you tell about my order?” Boasberg inquired. Ensign stated that he communicated the information to contacts at the Department of Homeland Security and officials from the State Department, among others.

At Boasberg’s request, Ensign provided the names of the individuals involved, which the judge carefully noted down, confirming spellings and titles as he went.

This hearing is part of ongoing legal challenges regarding the Trump administration’s use of the Alien Enemies Act. It follows Boasberg’s earlier order demanding an explanation from officials about why they failed to halt the deportation flights and whether they knowingly violated the court’s directive. Both parties are scheduled to reconvene next week for arguments on the plaintiffs’ preliminary injunction motion, set for Tuesday.