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 United States were in flight on March 15 when a federal judge in Washington ordered the Trump administration to turn them back.

Instead, the planes landed in El Salvador hours later, setting 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 was not carried out.

That fight entered a critical phase Friday when U.S. District Judge James Boasberg restarted an investigation into whether the Republican administration deliberately ignored his instructions, allowing the planes to continue on their way to El Salvador.

The judge had previously concluded that this was the case and threatened to hold the responsible official(s) in contempt. The administration has denied any violations.

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

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

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

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

Fogel said the questions raised by Boasberg’s contempt investigation — whether 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 difficult for him to let it go,” the judge said.

O’Grady, who served in Alexandria, Va., just outside Washington, for 16 years, thanked Boasberg for his efforts to establish the facts.

“He makes sure his record is absolutely clear,” O’Grady said.

On Friday, Boasberg ordered the administration to submit statements by December 5 from all officials involved in the decision not to return flights to the United States. He said he would then decide whether to seek the testimony of witnesses.

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

Justice Department lawyers had urged him to drop the investigation, but Boasberg said he had to determine whether Homeland Security Secretary Kristi Noem, or someone else, “should be referred for possible contempt proceedings.”

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

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

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

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

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

Both planes had already left U.S. territory and airspace, so the migrants on board had already been “deported” and therefore did not fall within the scope of the court 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 that 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 interpreted” as only prohibiting the government “from expelling detainees from the territory of the United States,” wrote Gregory Katsas, a judge on the U.S. Court of Appeals for the Washington, D.C. Circuit. Katsas was nominated by President Donald Trump.

Trump officials have been angered by judicial review and have repeatedly challenged judges’ authority to review executive branch policies, particularly on immigration.

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

Noll said he expects the Justice Department to fight the investigation from the start, with “lots of calls and chest-thumping” that Boasberg is overstepping his authority.

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

In July, the Justice Department filed a misconduct complaint against him, alleging that 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 framed the contempt investigation as an effort to uphold the U.S. Constitution, which he said requires compliance with court orders. Separately, he is considering a request to force the administration to give at least 137 of the migrants, who are now back in Venezuela, the opportunity to challenge their gang designation.

He accused Trump administration officials of rushing the migrants out of the United States and said significant evidence had surfaced indicating many of them were not linked to the Tren de Aragua gang.

But history shows that such sanctions are rarely imposed or allowed to oppose the government.

A survey of thousands of federal court opinions published in the Harvard Law Review in 2018 found 82 contempt convictions against government officials and agencies since the end of World War II. Judges imposed or attempted to impose fines in 16 of those cases, but higher courts blocked them in all but three cases.

Prison sentences are even rarer. Justices have imprisoned or credibly threatened to incarcerate a federal agency official in just four cases, and high courts have also intervened to block punishment, according to the study by Nicholas Parrillo, a professor at Yale Law School.

Noll, the Rutgers law professor, said that if the investigation moves forward, it could influence the public debate over whether the administration can legally carry out its mass deportation policy.

“A lot of the power of a district court comes simply from its ability to put an issue before the public,” he said Tuesday in a telephone interview.