Judge Boasberg poised to hold Trump admin in contempt, takes down names of DHS officials: 'Pretty sketchy'

U.S. District Judge James Boasberg on Thursday grilled Trump administration lawyers over whether they defied a court order blocking deportations under a wartime immigration law — a potential step toward holding the administration in contempt.

At issue is the administration’s use of the 1798 Alien Enemies Act to deport Venezuelan nationals, including alleged members of the violent Tren de Aragua gang. Boasberg pressed Deputy Assistant Attorney General Drew Ensign on why the government appeared to ignore an emergency injunction last month halting those deportations.

The administration has appealed the underlying case to the Supreme Court. But for now, Boasberg is weighing whether there is probable cause to move forward with contempt proceedings — a question that remained open after a tense exchange in court.

Boasberg said he would issue a decision as early as next week on how to proceed if he finds grounds to hold the administration in contempt.

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During the hearing, Ensign was repeatedly questioned about who in the Trump administration had information about the flights and when the three deportation flights left U.S. soil for El Salvador. At least 261 migrants were deported that day, including more than 100 Venezuelan nationals who were subject to removal "solely on the basis" of the law 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. 

Ensign said yes, to which the judge responded: "It seems to me the government acted in bad faith that day." 

"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," Boasberg said.  

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He repeatedly questioned Ensign about his knowledge of the flights and whether any related materials were classified, which could have triggered state secrets protections.

Government lawyers have refused to share information in court about the deportation flights, and whether the plane (or planes) of migrants knowingly departed U.S. soil after the judge ordered them not to do so, citing national security protections. 

But according to Ensign, that may not have been an issue. He told Boasberg the flight information likely wasn’t classified, prompting the judge to wonder aloud why it hadn’t been shared with him in an ex parte setting.

"Can you think of one instance" where the state secrets privilege was invoked using unclassified info? he asked Ensign, who struggled to respond.

"Pretty sketchy," Boasberg said aloud in response.

Another focus of Thursday’s hearing was timing — both when President Donald Trump signed the proclamation authorizing use of the Alien Enemies Act, and when federal agents began loading planes with migrants bound for El Salvador.

Boasberg noted that the Trump administration began loading the planes the morning of March 15, hours before the flights left the U.S.

"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 pressed the lawyer over the names, locations and agencies of individuals who were privy to the removals, as well as internal conversations with other administration officials who may have been listening in to the court proceedings.

"Who did you tell about my order?" Boasberg asked. "Once the hearing was done, who did you tell?"

Ensign says he relayed the information to Department of Homeland Security contacts and State Department officials, among others.

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He listed the names of the individuals, at Boasberg's request, which the judge then carefully transcribed onto a pad of paper, interjecting at times to clarify the spelling or ask for their job titles.

The hearing is the latest in a flurry of legal battles over the Trump administration’s use of the Alien Enemies Act. It follows Boasberg’s order requiring officials to explain why they failed to comply with his directive to return the deportation flights — and whether they knowingly defied the court.

Boasberg told both sides he would see them again next week for arguments on the plaintiffs’ preliminary injunction motion, set for Tuesday.

The hearing also marks the latest clash between Trump and Boasberg, whom the president has publicly denounced as an "activist" judge and called for his impeachment.