Trump officials test limits of courts’ power to constrain their actions

by Justin Jouvenal, Natalie Allison, Ann E. Marimow

(c) 2025 , The Washington Post


The Trump administration is testing the limits of the federal court system to constrain the president, brushing aside court orders, harshly attacking judges and, in some cases, finding ways to circumvent adverse rulings.

The showdown reached a crescendo over the weekend when officials appeared to flout a judge’s order that barred the President Donald Trump from using a wartime authority for deportations and said the government should immediately turn around any flights containing such deportees. The Trump administration is appealing the ruling.

White House press secretary Karoline Leavitt insisted Monday that the administration acted within “the bounds of immigration law in this country,” even though plane loads of Venezuelan deportees landed in El Salvador hours after U.S. District Judge James Boasberg issued both his verbal and his written order.

“We are quite confident in that, and we are wholly confident that we are going to win this case in court,” Leavitt told reporters. She also said there are “questions about whether a verbal order carries the same weight as a … written order,” which is not a distinction generally recognized in court.

Several legal experts said the deportation flights mark a dramatic – and troubling – escalation in the Trump administration’s pushback against the courts, which has grown more aggressive in recent weeks as the administration faces a deluge of lawsuits seeking to restrain it.

White House “border czar” Tom Homan defended the flights, telling Fox News on Monday that Boasberg’s orders came too late for the court to have jurisdiction over the matter. “We’re not stopping,” Homan said, echoing the defiance other administration officials showed on social media Sunday. “I don’t care what the judges think.”

Those challenging the deportations have asked Boasberg to force government officials to explain under oath whether they violated his order in the case. The judge has scheduled a hearing for Monday at 5 p.m.

The moves represented a breakdown in the fragile balance of powers between the branches of government, according to some legal experts. Others offered more modulated assessments while acknowledging that the judicial system was being put under intense strain.

Steve Vladeck, a Georgetown University law professor, said the country is seeing “an unprecedented degree of resistance, willful or otherwise, to judicial mandates against the federal government.”

“It’s hard to imagine that this is going to get better before it gets worse,” Vladeck said in an email. “If the government is correct that these orders are legally flawed, it should be appealing them, not resisting them.”

Michael J. Gerhardt, a professor of constitutional law at University of North Carolina Law School, said the administration’s response to the judge’s order is probably the beginning of the first assertions of judicial defiance by Trump.

“We might just be there,” Gerhardt said, calling the administration’s rationale for allowing the deportation flights to complete their mission “really hard to believe.” Lawyers are obligated to “follow the law and respect and follow judicial dictates, and right now we have government officials who are operating lawlessly. I think this judge is in position to try to do what he can to rein them in.”

Trump secretly signed a proclamation Friday invoking the Alien Enemies Act of 1798 to deport, without the normal due process, Venezuelans over 14 who the government says belong to the Tren de Aragua gang. On Saturday, five Venezuelans filed suit to block their deportation under the order, and Boasberg issued a stay on their removal.

During an emergency hearing Saturday night, Boasberg extended his order to block the deportation of all Venezuelan migrants using Alien Enemies Act authority, which had only previously been invoked during wartime – including to imprison tens of thousands of Japanese Americans during World War II.

The judge ordered any planes carrying people being deported under the act to return to the United States.

By then, two flights had already taken off containing deportees. A third left after he issued his ruling, according to a timeline assembled by The Washington Post. All three flights landed after Boasberg gave his order to turn around.

Trump officials said Sunday that the planes contained 137 alleged gang members deported under the Alien Enemies Act. They have made it clear that they weren’t going to wait for the courts to bless their decision to carry on with the flights to El Salvador, a plan that one White House official, speaking on the condition of anonymity to discuss internal strategy, said was hatched by deputy chief of staff for policy Stephen Miller and Department of Homeland Security Secretary Kristi L. Noem.

Trump’s advisers argue that they are merely making use of legal mechanisms that are already in place for the president, despite the fact that some – like the Alien Enemies Act – have hardly been used in modern history.

“But it’s on the books,” said a second White House official, also speaking on the condition of anonymity to discuss the administration’s thinking.

On Sunday, a flurry of posts by Trump-aligned social media influencers and even White House officials themselves cheered the administration’s actions – sharing video clips set to hip-hop music that showed tattooed, shackled men being led off planes and shaved inside the mega prison in El Salvador.

White House staff quickly mobilized its network of influencers and allies to boost the content, a way to “flex our muscles,” the second administration official said, noting that the White House is “in this sort of permanent campaign mode” as it works to make the public aware of actions that polling shows are broadly popular.

Immigration – as was the case during Trump’s successful campaign last year – is at the top of that list.

While some of the White House public statements were viewed by Trump critics as flippant and defiant of the judge’s ruling, administration officials consulted with lawyers and top leaders of the National Security Council, State Department, Department of Defense, DHS and other entities about messaging ahead of making some of their social media posts and remarks, the second White House official said.

Top White House advisers say they are confident in the actions they’re taking and believe Trump’s team is being sufficiently cognizant of the forthcoming court fights.

“I say this with no disrespect to any of the previous administrations, and I’m trying to phrase this as delicately as possible,” the second official said. “This White House has the balls to do it.”

Plaintiffs in other cases have also accused the Trump administration of violating court orders.

Attorneys for Rasha Alawieh, a 34-year-old kidney transplant specialist from Brown University, say the government “willfully” violated a ruling barring her deportation. Alawieh was sent back to Lebanon on Friday after a cousin petitioned a judge in Massachusetts to keep her in the country and won a restraining order. The cousin said in court filings Alawieh had a valid visa.

Attorneys for global health groups that have sued to restart billions in foreign aid payments said in a status report Friday that Trump administration had yet to fully comply with a judge’s order, despite repeated rulings mandating payments in recent weeks.

The government has told the court it is analyzing the order to expend the foreign assistance funds and “will do so in consultation with the Office of Management and Budget.”

Last month, U.S. District Judge John J. McConnell Jr. of Rhode Island ruled that the administration had violated the “plain text” of his order lifting a temporary freeze on trillions of dollars in federal grants and loans.

The Trump administration has faced initial setbacks in court over its blitz of executive orders, which have triggered more than 120 lawsuits. Judges have blocked many of the administration’s most high-profile efforts, including ending birthright citizenship, firing thousands of probationary workers and dismantling some federal diversity initiatives.

Trump officials have chafed at those rulings, particularly nationwide injunctions issued by federal district court judges. Vice President JD Vance has said judges “aren’t allowed to control the executive’s legitimate power,” while Elon Musk has called for the impeachment of judges.

The administration also railed against temporary restraining orders in a recent Supreme Court filing that asks the justices to allow Trump’s ban on birthright citizenship in some states, leaving his order paused by lower courts only in states that have specifically sued to stop it.

“This Court should declare that enough is enough before district courts’ burgeoning reliance on universal injunctions becomes further entrenched,” acting solicitor general Sarah Harris wrote. “Years of experience have shown that the Executive Branch cannot properly perform its functions if any judge anywhere can enjoin every presidential action everywhere.”

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Jonathan Edwards and Ben Brasch contributed to this report.