'White House is hanging these lawyers out to dry': Trump deportation hearing draws mockery

The Department of Justice appeared before Judge James Boasberg for a Thursday contempt hearing, discussing the specifics of whether the U.S. government defied his temporary restraining order to prevent deportations to El Salvador. In a court hearing on March 16, Boasberg said that two flights carryi...

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U.S. President Donald Trump speaks during his visit to the Department of Justice to address its workers, in Washington, D.C., U.S., March 14, 2025. REUTERS/Nathan Howard

The Department of Justice appeared before Judge James Boasberg for a Thursday contempt hearing, discussing the specifics of whether the U.S. government defied his temporary restraining order to prevent deportations to El Salvador.

In a court hearing on March 16, Boasberg said that two flights carrying immigrants to El Salvador and Honduras must immediately turn around. The judge also issued a temporary restraining order barring President Donald Trump from using an 18th-century law to justify additional deportations.

Boasberg then inquired further about whether his order was violated and, if so, to uncover who should be held in contempt.

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Legal journalist Adam Klasfeld noted that the judge appeared willing to hold some administration officials in contempt of court.

Other legal analysts mocked the contentious hearing and the problematic spot the president put the Justice Department in.

"I’m glad that I’m not Drew Ensign," said Lawfare's Anna Bower, speaking of the deputy assistant attorney general arguing the case.

Among the questions asked by Boasberg was: "Whom did you tell about the oral order, once we got off the phone, when the hearing's done, who did you tell about the hearing. Who wasn't on the call?"

Ensign said he relayed it to "contacts at the DHS and to people at the State Department."

But Boasberg wanted names.

"It’s getting to the point we are going to venture into crime-fraud exception territory here. The White House is hanging these lawyers out to dry," national security lawyer Bradley P. Moss said on Bluesky about the exchange.

Appellate lawyer Matthew Stiegler agreed, "This line of inquiry seems likely to be excruciating for Ensign."

"Boasberg [is] now asking Ensign what the best way would be to obtain information on 'potential contemnors' (ie who decided not to turn the planes around), which feels a bit like asking someone how they would like to be executed," said Lawfare's Quinta Jurecic.

She later added: "Counterpoint to the demands for contempt right away: the longer this takes, the lower Trump's popularity gets, the harder it is for him to marshal any political support for defying the courts (a position that is already extremely unpopular)."

Legal commentator Ken White pointed to a moment in which Boasberg requested a kind of tick-tock of what Ensign was told and when he was told it.

"This is the judicial equivalent of 'we need to talk,'" said White.

Toward the end of the hearing, Boasberg commented that he was interested in finding out specifics "as we proceed with potential contempt proceedings." He asked Ensign what he thinks the best way to get that information would be. Should they be declarations, depositions or bringing people under oath? Ensign says he doesn't think that's necessary.

That prompted Stiegler to "Actual lol."

"While this all hasn’t gone the way I thought it should, I must confess today’s hearing was satisfying," he summed up.

"Since I was critical of Boasberg's cautious approach before, I'll be transparent and offer my (unsatisfying) updated two cents," he continued. "My #1 source of urgency before was [the] belief that the administration was choosing court defiance, both open and evasive. I thought it was critical that Boasberg take the judiciary's best shot at stopping it, instead of leaving other, more vulnerable courts exposed.

"Two weeks down the road, I'm not sure defiance is the current path. And I think it's very fair to ask if Boasberg's steady, careful, I'm-watching-you approach is responsible for that shift, without risking all the judiciary's chips in the pot as I wanted. Maybe. I guess what I really think at this point is that I'm not confident that I'm following it all carefully enough to have a solid view about it. I know that's not a thing one says online, but..."

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