After the Trump administration rushed nearly 240 Central American immigrants onto charter planes last month and flew them — most without hearings — to a prison in El Salvador, the courts responded with a flurry of orders more or less instructing Trump officials to figure out a way to give them the due process they had been denied.
But for much of the past few weeks, the White House has dodged, dragged its feet and found other ways to defy some of those orders. And that has led to a remarkable development.
Two federal judges in Washington and Maryland handling cases arising from the deportation flights have now declared that they have reason to believe that Trump officials have acted in bad faith by failing to comply with their decrees. To get to the bottom of the obfuscation, the judges have made plans for searching inquiries into who in the administration may have been responsible.
The threat of the investigations has come at an especially fraught moment: just as President Trump and his advisers are increasingly butting heads with the courts and are testing the traditional balance of power between the judicial and executive branches. The jurists’ dual moves have brought the two supposedly coequal parts of the government closer than ever to an open confrontation.
The prospect of that rift has become so glaring that it made its way on Thursday into an almost mournful order regarding one of the deportation cases written by Judge J. Harvie Wilkinson III, a conservative Reagan appointee, who sits on the U.S. Court of Appeals for the Fourth Circuit in Virginia.
The purpose of the order was to reaffirm that the White House needed to play a more active role in seeking the release of a Maryland man, Kilmar Armando Abrego Garcia, who was flown last month to a prison in El Salvador, despite a court order expressly forbidding him from being sent there.
But Judge Wilkinson devoted long passages of his ruling to bemoaning the incipient breakdown of the nation’s constitutional order.
“Now the branches come too close to grinding irrevocably against one another in a conflict that promises to diminish both,” he wrote.
“This is a losing proposition all around,” he added. “The judiciary will lose much from the constant intimations of its illegitimacy, to which by dent of custom and detachment we can only sparingly reply. The executive will lose much from a public perception of its lawlessness and all of its attendant contagions.”
The battle between the White House and the judges has been playing out not only in the courtroom but also in more typically political arenas.
On social media last month, Mr. Trump called for the impeachment of one of the judges, James E. Boasberg, the chief judge in Federal District Court in Washington. And this week, during an Oval Office news conference, the president effectively said that he was powerless to comply with an order by the other, Judge Paula Xinis of Federal District Court in Maryland, to “facilitate” the release of Mr. Abrego Garcia from El Salvador.
Some of Mr. Trump’s top advisers have echoed his attacks against Judge Boasberg, claiming that the judge overstepped the limits of his authority by issuing his original order pausing deportation flights of Venezuelan immigrants to El Salvador. The administration invoked the expansive powers of a wartime statute called the Alien Enemies Act to remove them.
Other advisers, including Stephen Miller, Mr. Trump’s chief policy aide, twisted the facts in the case before Judge Xinis. Mr. Miller declared this week — blatantly contradicting other administration officials — that Mr. Abrego Garcia had not been mistakenly sent to the Salvadoran prison but had in fact been lawfully deported there.
The language used in the orders and the hearings emerging from these cases suggests how seriously the judges in the five separate courts that have touched them are taking the administration’s recalcitrant approach. The words and phrases they have employed — “grievous error,” “shocks the conscience,” “unconscionable” — are themselves an indication of how out-of-bounds and unchastened they believe the White House has been.
On Tuesday, Judge Xinis rebuked a lawyer for the Justice Department, telling him that, as far as she could tell, “nothing had been done — nothing” to comply with her directives in the Abrego Garcia case.
The next day, Judge Boasberg complained that the government had shown a “willful disregard” for his instructions. Even though he had given department lawyers “ample opportunity to rectify or explain their actions,” he added, “none of their responses has been satisfactory.”
But while it may seem like the judges and the White House are headed for an immediate collision, the crash, should it come, is more likely to happen in slow motion. That is because the legal system is almost certain to afford the White House additional opportunities for evasion and delay.
Judge Xinis set up her investigation first, announcing at a hearing in Maryland on Tuesday that the administration would have to answer questions — both in writing and in depositions — about what it had done so far to get Mr. Abrego Garcia out of prison in El Salvador and what further steps it planned to take.
A written order set the contours for the inquiry. Lawyers for Mr. Abrego Garcia, whom the administration has accused of belonging to the violent street gang MS-13, would get 15 requests for documents and the chance to depose as many as six administration officials.
Judge Xinis said the lawyers could explore “the lawful basis, if any” for Mr. Abrego Garcia’s continued custody at the Salvadoran prison, a notorious detention center known as CECOT. She also suggested that the lawyers could seek information about the deal the White House had struck with the Salvadoran government to house all of the nearly 240 immigrants at CECOT.
Less than 24 hours later, Judge Boasberg weighed in, saying that he would open expansive contempt proceedings unless the White House did what it had failed to do from the start: give the Venezuelans it had deported to El Salvador under the Alien Enemies Act a chance to challenge both the way the law was used and the administration’s accusations that they were members of another street gang, known as Tren de Aragua.
In his own written order, Judge Boasberg made clear that he would seek to pin down who in the administration was behind what he described as the “willful disregard” of his oral instructions. At the time, he said that any deportation flights headed to El Salvador under the Alien Enemies Act needed to be halted at once and that any planes already in the air should turn around.
He also explained in detail the increasingly painful measures the administration might face if it decided not to provide due process to the Venezuelan men. He said it would begin with sworn declarations and then move on, if needed, to courtroom testimony under oath.
If he was still unable to determine who had given the directions to disobey his order, he said he would refer the case to the Justice Department for criminal prosecution. Aware that the department under Mr. Trump’s control would not be likely to file charges, Judge Boasberg said he would play a final card: a special provision of the criminal contempt law that would, in effect, allow him to appoint an outside prosecutor.
So far, the case of the Venezuelans and Mr. Abrego Garcia’s case have proceeded along separate tracks, largely because they are based on different facts and legal issues.
While both involve accusations that the government deprived the men of hearings before they were deported, the Venezuelans have been challenging the use of the Alien Enemies Act to remove them from the country. Mr. Abrego Garcia was removed under a more traditional deportation process.
But in recent days, the cases have inched closer together. That is because two Supreme Court decisions, issued separately in each of the matters, have, over time, become increasingly relevant to both.
The justices ruled first in the Venezuela case, finding that the men must be allowed to challenge their deportations before being flown out of the country, but only in the specific places where they were being held.
Three days later, the justices rendered a decision in Mr. Abrego Garcia’s case, ruling that the administration had to “facilitate” his release from Salvadoran custody and essentially figure out a way to give him the sort of due process he would have been afforded if he had not been wrongly sent there.
Taken together, these two rulings suggest that more could still be done to provide due process to the immigrants who were sent to El Salvador, even though they are no longer on U.S. soil. The rulings also suggest that the administration may have to do more work to try to secure the men’s release from CECOT — despite the fact that Mr. Trump has said he is powerless to do so.
Indeed, lawyers for the Venezuelans have already said they plan to use both rulings in a renewed attempt to bring them back from El Salvador.
The lawyers, citing the justices’ ruling in their own case, said that it is legal to file a challenge to the deportations in front of Judge Boasberg in Washington even though that is not where the men are being held. They say that Washington is the proper venue for the legal action when prisoners are in custody overseas.
The lawyers have also said they will seek to use the Supreme Court ruling in the Abrego Garcia case to force the White House to free the men from prison in El Salvador.
They have told Judge Boasberg that he has “the authority to order the government to facilitate the return” of the men, just like the justices have said that Judge Xinis has the authority to make White House help in the return of Mr. Abrego Garcia.
Mattathias Schwartz contributed reporting.
Alan Feuer covers extremism and political violence for The Times, focusing on the criminal cases involving the Jan. 6 attack on the Capitol and against former President Donald J. Trump.
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