Trump officials and judge face off over flights to El Salvador in rare, high-stakes contempt probe

Two planes carrying Venezuelan migrants out of the U.S. were midair on March 15 when a federal judge in Washington ordered the Trump administration to turn them around.

Instead, the planes landed in El Salvador hours later, touching off an extraordinary power struggle between the judicial and executive branches of the U.S. government over what happened and why the judge’s order went unexecuted.

That fight entered a critical phase on Friday when U.S. District Judge James Boasberg relaunched an investigation to determine whether the Republican administration deliberately ignored his instruction, letting the planes continue onto El Salvador.

The judge previously concluded it did and threatened to have the responsible official or officials prosecuted on a contempt charge. The administration has denied any violation.

But an appeals court threw Boasberg’s decision out. The contempt probe appeared dead until in yet another twist, a larger panel of judges on the same appeals court ruled on November 14 that the investigation could proceed.

Here’s a look at what makes this case unusual and what could happen now:

Criminal contempt inquiries such as Boasberg’s are extremely rare

They are a last resort, former federal judges Jeremy Fogel and Liam O’Grady told The Associated Press in an interview Monday conducted on Zoom.

“The judge has to believe that some line may have been crossed that you can’t ignore,” said Fogel, who spent 20 years on the bench in Northern California before retiring in 2018.

Fogel said the issues raised by Boasberg’s contempt probe — whether the migrants were deprived of their due process rights and whether the court’s authority was flouted — meet that standard.

“Whatever actually happened, I think it would be very hard for him to just let it go,” the judge said.

O’Grady, who served in Alexandria, Virginia, just outside Washington, for 16 years, credited Boasberg for his efforts to determine the facts.

“He’s making sure that his record is absolutely clear,” O’Grady said.

Boasberg wants to start with written statements

On Friday, Boasberg ordered the administration to submit declarations by December 5 from all officials involved in the decision not to return the flights to the U.S. He said he will then decide whether to seek testimony from witnesses.

The declarations should detail the officials’ roles in the decision, the judge said in the brief order.

Justice Department attorneys had urged him to abandon the probe, but Boasberg said he must determine whether Homeland Security Secretary Kristi Noem or anyone else “should be referred for potential contempt prosecution.”

“In other words, the Court must decide if: (1) the court order was ‘clear and reasonably specific’; (2) ‘the defendant violated the order’; and (3) ‘the violation was willful,’” he wrote.

In a court filing on Tuesday, Justice Department attorneys said Noem decided the migrants aboard the flights could be transferred to El Salvador after receiving advice from the Homeland Security department’s acting general counsel, Joseph Mazzara.

Mazzara had received legal advice about the planes from Deputy Attorney General Todd Blanche and Principal Associate Deputy Attorney General Emil Bove, according to the filing.

The administration has defended its decision about the planes

The judge’s directive to return them was made verbally in court but not included in his written order, government attorneys said in the court filing on Tuesday.

That order blocked the administration from removing “any of the individual Plaintiffs from the United States for 14 days,” but said nothing about the flights already airborne.

The two planes had already departed U.S. territory and airspace, so the migrants aboard them had already been “removed” and therefore fell outside of the court’s order, Justice Department lawyers said in the court filing.

“Accordingly, the Government maintains that its actions did not violate the Court’s order — certainly not with the clarity required for criminal contempt — and no further proceedings are warranted or appropriate,” they wrote.

A federal appeals court judge said in August that the administration’s interpretation of Boasberg’s order was plausible. The order “could reasonably have been read” as only prohibiting the government from “expelling detainees from United States territory,” wrote Gregory Katsas, a judge on the U.S. Court of Appeals for the D.C. Circuit. Katsas was appointed by President Donald Trump.

The White House has been hostile to judges that check its power

Trump officials have chafed at judicial oversight and repeatedly contested the power of judges to review executive branch policies, particularly on immigration.

“There is a deliberate effort to push the boundaries and try to curtail the authority of trial courts,” said David Noll, a Rutgers Law School professor who writes about the intersection of the law and politics.

Noll said he expects the Justice Department to fight the inquiry from the start, with “lots of appeals and chest thumping” that Boasberg is exceeding his authority.

Trump has already attacked Boasberg. After the March 15 ruling, Trump derided the judge as a “troublemaker and agitator” and called for his impeachment. Boasberg was nominated to the bench by Democratic President Barack Obama and currently serves as the chief judge of the federal court for the District of Columbia.

In July, the Justice Department filed a misconduct claim against him, alleging he told Chief Justice John Roberts and other federal judges in March that the administration would trigger a constitutional crisis by disregarding federal court rulings.

Boasberg has framed the contempt inquiry as an effort to uphold the U.S. Constitution, which he says requires compliance with judicial orders. Separately, he is considering a request to require the administration to give at least 137 of the migrants, who are now back in Venezuela, a chance to challenge their gang designation.

He has accused Trump administration officials of rushing the migrants out of the U.S. and said significant evidence had surfaced indicating that many of them were not connected to the Tren de Aragua gang.

Contempt findings can carry fines and prison time

But history shows such punishments are rarely issued or allowed to stand against the government.

A survey of thousands of federal court opinions published in the Harvard Law Review in 2018 turned up 82 contempt findings against government officials and agencies since the end of World War II. Judges issued or tried to issue fines in 16 of those cases, but higher courts blocked them in all but three.

Prison time is even more uncommon. Judges locked up or credibly threatened to lock up a federal agency official in only four of the cases, and high courts similarly intervened to block the sanction, the study by Yale Law School professor Nicholas Parrillo found.

Noll, the Rutgers Law professor, said if the inquiry moves ahead, it could influence public debate about whether the administration can carry out its mass deportation policy legally.

“A lot of a district court’s power just comes from the ability to get an issue in front of the public,” he said in a phone interview on Tuesday.