D.C.’s chief judge on Thursday indicated he may find that the Trump administration rushed Venezuelans onto planes bound for a Salvadoran prison last month in a way meant specifically to avoid court intervention mid-operation.
Now the question is who, if anyone, at the White House put together the operation and kept it pushing forward — even as a federal judge tried to block it.
Sworn declarations and court testimony from top Trump officials could soon be underway.
During a court hearing in the ongoing legal battle over President Donald Trump’s use of a wartime measure to target “enemy aliens,” U.S. District Judge James Boasberg raised the possibility of finding federal officials in contempt of court — deepening the constitutional power struggle between the executive branch and the nation’s courts.
Boasberg spent half an hour Thursday afternoon questioning Drew Ensign, the Department of Justice’s new deputy assistant attorney general overseeing immigration litigation. But the judge appeared suspicious of the federal prosecutor’s answers, as Ensign repeatedly claimed total ignorance or reached for legal justifications to keep the judge in the dark about why planes full of migrants didn’t circle back to the United States after the judge had forbidden them from deporting these people.
“What you were willing to do by trying to do this as quickly as possible and avoid being enjoined by the court was to risk putting people on those planes who shouldn’t have been on those planes in the first place,” Boasberg said, citing the case of a legally protected Salvadoran father whom the government has admitted it deported in error.
The Trump administration is throwing out every tool in the shed to try to stop the judge from learning more about the operation, having appealed the case to the Supreme Court in only two weeks and invoking the rare “state secrets privilege” to erect a wall that the judiciary might not be able to overcome.
But on Thursday, the Justice Department raised yet another barrier: protections that typically pertain to legal strategy between a lawyer and their client.
“Who gave the order that the planes not turn around?” Boasberg asked.
“That essentially would be subject to attorney-client privilege,” Ensign said.
“Because?” the judge said with a tone of bewilderment. “Who made the decision to either not tell the pilots anything or tell them to keep going?”
“I haven’t been told,” Ensign eventually said.
The White House, Justice Department and immigration law enforcement teams are up against a tight timeline, one that Boasberg bore into on Thursday as he tries to determine which officials were responsible for continuing the fast-moving deportations.
Government records show that on Friday, March 14, Trump quietly signed a proclamation invoking the 1798 Alien Enemies Act to target Venezuelans and brand them gang members without a trial. Immediately thereafter, migrants from several nations were rounded up by federal agents and placed on buses headed for three planes in Texas. Human rights advocates tried to intervene with a lawsuit shortly after midnight Saturday, and Boasberg held morning and afternoon court hearings that sought to hit the brakes on the situation.
Boasberg questioned why the president delayed publicizing the proclamation by an entire day while federal agents undertook the operation.
“So, you don’t think, then, that it has anything to do with trying to put measures in place to get people subject to the proclamation to be removed from the country before it was possible to challenge it legally, do you?” he asked.
“I don’t know those operational details,” Ensign responded.
Trump has since professed, “I don’t know when it was signed, because I didn’t sign it.” Ensign claimed he’d heard about the statement but hadn’t seen it himself — and asked the judge not to consider the assertion “relevant.”
Although five migrants managed to sue to halt their deportations and are now part of this class action lawsuit, hundreds of others were transferred to El Salvador’s Terrorism Confinement Center. Boasberg tore apart government legal arguments that all these detained migrants somehow had the ability to challenge their rapid removals in court during the “rush” to get them into a prison in El Salvador widely accused of torturing inmates.
“The courts weren’t open… You wouldn’t typically say the window between 1 a.m. and 7 a.m. on a Saturday is sufficient time to challenge government action, would you?” he asked, noting that the government scramble was not “anything close to common.”
The judge said that the administration could have determined it was “better to be safe than risk violating the order” and simply held off on the Saturday afternoon operation.
“Why wouldn’t the wise, prudent, considered route be that?” he asked.
The judge also took issue with the White House’s decision to invoke the powerful state secrets privilege to withhold information from him, grilling the Justice Department on whether the information was classified — only to get an “I don’t know” in response.
“Can you point me to a single case where unclassified information is covered by the state secrets privilege?” Boasberg asked, adding that the Trump administration’s decision to invoke such a powerful legal tool was done “pretty sketchily.”
After much prodding, Ensign eventually revealed that several top administration officials were looped in on the courtroom events that Saturday during the operation, including State Department legal adviser James L. Bischoff; Department of Homeland Security acting general counsel Joseph N. Mazzara; Trump’s nominee to officially fill that position, Florida Attorney General chief of staff James Percival; and James McHenry, who leads the DOJ office that runs the nation’s immigration courts.
When Ensign declined to name others, the judge warned that the inquiry could get much more serious.
“I’m certainly interested in finding that out,” he said. “As we proceed with potential contempt proceedings, that may become relevant.”
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Jose Pagliery is a reporter at NOTUS.