A federal judge grilled Trump administration lawyers Friday over the deportation of Venezuelan nationals to El Salvador despite an earlier court order explicitly blocking the move. It was the latest in a legal dispute that could reach the Supreme Court.

During a motion hearing, U.S. District Court Judge James Boasberg questioned Deputy Assistant Attorney General Drew Ensign about why the Trump administration failed to comply with an emergency court order that temporarily blocked its use of the 1798 Alien Enemies Act to deport Venezuelan nationals, including alleged members of the gang Tren de Aragua, from U.S. soil for 14 days.

At least 261 migrants were deported Saturday from the U.S. to El Salvador, including more than 100 Venezuelan nationals who were subject to removal “solely on the basis” of the law temporarily blocked by the court.

Boasberg used the first portion of Friday’s hearing to press Ensign for details over the government’s deportation flights to El Salvador.

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U.S. District Court Judge James Boasberg  (Getty)

“Why was this proclamation signed in the dark on Friday, early Saturday morning, and then these people rushed onto the planes?” Boasberg asked Justice Department attorneys. “To me, the only reason to do that is if you know the problem, and you want to get them out of the country before a suit is filed.”

Ensign was also pressed at length over what he knew about the deportations during last week’s court hearing, when Boasberg ordered the Trump administration to temporarily halt any planned removals of Venezuelan migrants subject to the Alien Enemies Act.

Boasberg also issued a bench ruling Saturday ordering the immediate return of any planes deporting the Venezuelan nationals targeted for deportation under the Alien Enemies Act.

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“Can I ask you now how you interpreted that statement when we had a conversation on Saturday?” he asked Ensign. “Did you not understand my statement during that hearing?

“You told me you had no details on the plane flights. Then we held a recess for 38 minutes for you to find details,” the judge reminded Ensign. “And then when you came back — and even though the flights were in the air — you represented that you had no details of the flights?” 

“That’s correct,” Ensign responded, telling the judge no one would give him the information he sought about the deportation flights. “I did not know they were in the air.”

Former President Donald Trump’s personal attorneys, Todd Blanche, Emil Bove and John Lauro, depart federal court in Washington, D.C., in 2024.  (Anna Moneymaker/Getty Images)

Boasberg has ordered Trump administration officials to explain by Tuesday why they failed to comply with his order requiring the deportation flights to return and whether they knowingly defied his ruling. 

Though the judge acknowledged the Trump administration has “wide latitude” to enforce immigration law, he has repeatedly expressed frustration with the government and its failure to answer major questions about the flights.

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He reiterated these concerns Friday and raised new concerns about the administration’s apparent defiance of federal judges.

“The hypotheticals are frightening,” Boasberg told Ensign. “If the courts can’t review” the administration’s use of the wartime-era deportation law, “then the president could say anyone is invading. If some foreign fisherman comes into U.S. waters, the president could say that’s an invasion.

“Even you would say that’s alarming.”

“That’s up to Congress,” Ensign responded.

President Donald Trump arrives with Attorney General Pam Bondi to speak at the Justice Department in Washington, March 14, 2025.  (Pool via AP)

In a court order filed Thursday, Boasberg castigated lawyers for the Justice Department for failing to answer his questions about the deportation flights, even after he let them do so under seal, noting that the government had “again evaded its obligations.” 

It remains unclear whether the Trump administration will invoke the state secrets privilege in the court battle, which could allow it to withhold certain information for national security purposes.

In a court declaration filed Friday morning, U.S. Deputy Attorney General Todd Blanche told Boasberg he is aware of Cabinet-level discussions invoking that privilege. The administration could present that argument at an appellate court hearing next week.

Invoking that privilege “is a serious matter that requires careful consideration of national security and foreign relations, and it cannot properly be taken in just 24 hours,” Blanche told the court Friday. 

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President Donald Trump, for his part, demanded in a social media post Friday that the Supreme Court move to rein in federal judges who have blocked over 300 of his executive orders and actions. 

In a Truth Social post, Trump implored the Supreme Court to “STOP NATIONWIDE INJUNCTIONS NOW, BEFORE IT IS TOO LATE.”

“If Justice Roberts and the United States Supreme Court do not fix this toxic and unprecedented situation IMMEDIATELY, our Country is in very serious trouble!” he added.