U.S. District Judge James Boasberg didn’t hold back on Thursday as he grilled Trump administration lawyers over a potentially serious issue—whether they defied a court order halting deportations under a wartime immigration law. If proven, this could set the stage for a contempt ruling against the administration, an extraordinary move with major legal and political ramifications.
The Controversial Use of the 1798 Alien Enemies Act
At the heart of the issue is the administration’s reliance on the 1798 Alien Enemies Act to justify deporting Venezuelan nationals, including some alleged members of the Tren de Aragua gang—a notorious criminal organization. This law, originally designed for times of war, had been temporarily blocked by the court, but the government appeared to have continued deportations regardless.
Judge Boasberg was especially critical of Deputy Assistant Attorney General Drew Ensign, pressing him on why the government proceeded with deportations despite an emergency injunction last month that explicitly stopped such actions. With the administration appealing the case to the Supreme Court, Boasberg is left to determine whether there is enough cause to move forward with contempt proceedings. After a heated exchange, that question remains unresolved for now.
"Bad Faith" and Allegations of Non-Compliance
One of the most tense moments came when Boasberg questioned Ensign on whether the government was in full compliance with the court’s order.
“You maintain that the government was in full compliance on March 15, correct?” Boasberg asked.
“Yes,” Ensign replied.
The judge wasn’t convinced. “It seems to me the government acted in bad faith that day,” Boasberg shot back.
His skepticism only grew when Ensign struggled to provide clear answers about what officials knew and when. The judge repeatedly asked about the timeline of events—particularly when President Trump signed the proclamation activating the Alien Enemies Act and when federal agents began organizing the deportation flights.
Suspicious Timing and "Sketchy" Details
One major red flag for Boasberg was the timing of the deportation flights. The Trump administration began loading migrants onto planes bound for El Salvador on the morning of March 15—hours before the flights departed the U.S. This suggested prior knowledge and coordination before the official order was given, raising questions about whether officials acted in defiance of the court’s ruling.
“So then it’s not crazy to infer there was prior knowledge and actions ahead of the Saturday night deportations?” Boasberg asked Ensign.
The government’s lack of transparency only deepened the judge’s frustration. Lawyers refused to disclose details about the deportation flights, citing national security protections. Yet, Ensign admitted that the flight information itself was probably not classified—leading Boasberg to question why the details hadn’t been provided in an ex parte (private) setting.
“Can you think of one instance where the state secrets privilege was invoked using unclassified info?” Boasberg asked.
Ensign struggled to answer.
“Pretty sketchy,” the judge muttered in response.
Who Knew What—and When?
Another focal point of the hearing was identifying who in the administration knew about the deportation flights and when they were informed. Boasberg pressed Ensign for names, locations, and agencies involved in the removals. He specifically wanted to know who received information about the court order after it was issued and whether those officials took any steps to halt deportations.
“Who did you tell about my order?” Boasberg asked. “Once the hearing was done, who did you tell?”
Ensign said he passed the information along to Department of Homeland Security contacts and State Department officials, among others. At Boasberg’s request, he listed their names, which the judge carefully wrote down, occasionally stopping to clarify spellings and job titles.
A Heated Legal Battle Continues
This latest courtroom showdown is just one of many legal battles over the Trump administration’s use of the Alien Enemies Act. Earlier, Boasberg had demanded that officials explain why they failed to comply with his directive to halt deportations—and whether they deliberately ignored his order.
Both sides are expected to return to court next week for arguments on the plaintiffs’ preliminary injunction motion, scheduled for Tuesday.
Adding to the drama, this hearing marks yet another clash between Boasberg and Trump. The former president has repeatedly attacked the judge, calling him an “activist” and even pushing for his impeachment.
With Boasberg’s decision expected as early as next week, the stakes couldn’t be higher. If he finds grounds for contempt, it could deal a significant legal blow to the Trump administration and set a precedent for how future immigration policies are enforced. Stay tuned—this battle is far from over.
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