President Trump’s unprecedented flex of executive power has sent legal challengers scrambling to courts to pump the breaks.
But some of the president’s more extraordinary actions have been difficult to confront, as the administration barrels forward with an act-first, defend-later approach to its policy agenda.
“We were looking for any mechanism that would, so to speak, stop the trains here,” Andrew Goldfarb, a lawyer representing challengers to the Department of Government Efficiency (DOGE)’s takeover of the U.S. Institute of Peace (USIP), said at a hearing this week.
“Anything to stop the destruction that is going on,” he said.
More than 100 lawsuits have been filed opposing Trump’s executive actions and the ways his administration has sought to effectuate them, spanning the president’s crackdown on law firms, DEI, gender, controversial immigration and deportation policies and DOGE’s efforts to slim down the federal government.
In many challenges, judges have granted speedy injunctive relief. It’s far more complicated in others.
At the USIP hearing Wednesday, Goldfarb described how DOGE sought to reduce “essentially to rubble” the independent institute, established to help resolve and prevent violent conflicts. He said nearly all USIP’s board members were unlawfully removed before DOGE showed up with armed law enforcement officers to seize control of the building.
U.S. District Judge Beryl Howell raised alarm about the “offensive” way DOGE accessed the building. But she declined to grant the plaintiffs the temporary restraining order they sought, citing “confusion” in their complaint and a motion that made her “very uncomfortable.”
Timothy Zick, a professor at William & Mary Law School, said that litigating under such uncertainty is “extremely challenging.”
Courts must undergo fact-finding to make the legal determinations necessary to move a lawsuit forward, but that’s hard to do in an emergency, he said. While judges can grant emergency relief, a messy record makes it difficult to fashion relief that is appropriate.
“Without a good record of what has transpired, litigants and courts are at a distinct disadvantage,” Zick said.
Challenges to DOGE’s cutdown of the federal bureaucracy, in particular, have presented issues where there is uncertainty about the advisory group’s constitutional authority, he added.
A federal judge similarly denied requests for temporary restraining orders in a pair of lawsuits contesting efforts to detain migrants at Guantánamo Bay, backed by the American Civil Liberties Union.
ACLU lawyer Lee Gelernt said the challengers found themselves in a “Catch-22.” The migrants’ legal teams would not know if the government moved them to the Cuban detention camp until after it happened. But if they were sent there, it would cause irreparable harm due to the perilous conditions there like shackles and solitary confinement.
He noted that the administration had transferred migrants to the detention site then abruptly emptied it multiple times, complicating any legal challenge to the efforts.
“We don’t know that the moment we walk out of court they (won’t) be sent to Guantánamo,” Gelernt said during a hearing on the matter last week.
U.S. District Judge Carl Nichols denied their request, pointing to the fact that, at that time, no detainees with final orders of removal were being held at the facility. Less than a week later, the administration sent a new group of migrants there.
Claire Finkelstein, a University of Pennsylvania law professor, said the administration’s strategy has a “certain sense of gamesmanship.”
Though Trump has said he won’t violate court orders, the back-and-forth makes it difficult to figure out the truth of the situation at hand, she said.
“You’re playing Whack-a-Mole all the time,” she said. “I think that’s an intentional strategy.”
Barbara McQuade, a former U.S. attorney, said there’s still value in challenges where the landscape changes, making moot initial arguments.
“It may cause the administration to stop doing something that it doesn’t think will hold up in court, even if the court doesn’t, hasn’t decided yet,” she said.
In First Amendment challenges to Trump’s often-vague executive orders, lawyers have argued that confusion regarding how and when the administration will enforce the directives could have a chilling effect.
Howell, who is also overseeing the case over Trump’s order targeting the law firm Perkins Coie, pressed the Justice Department last week over why the president’s far-reaching order would not chill lawyers or the courts. She asked if the president should simply be trusted to “draw the right lines.”
“Yes, he has that power,” said DOJ chief of staff Chad Mizelle, who argued for the Trump administration.
In Trump’s anti-DEI orders, which have also been challenged in courts, the president does not clearly define “DEI” — which stands for diversity, equity and inclusion — leaving questions about which specific enforcement actions will occur if- violated, Zick said.
The U.S. Court of Appeals for the Fourth Circuit last week lifted a nationwide injunction prohibiting enforcement of several provisions of two DEI orders for that very reason. One judge wrote in a concurring opinion that “what the orders say on their face and how they are enforced are two different things.”
“As far as the Administration is concerned, the lack of specificity is a virtue,” Zick said. “It makes it harder for courts to assess the effect of the Orders, and in the meantime, affected parties may be chilled from engaging in activity or feel pressured to comply in anticipation of enforcement.”
The Trump administration has argued that the lack of specificity is beyond the government’s scope of duty.
DOJ lawyer Pardis Gheibi said during a hearing Wednesday in a lawsuit over the president’s DEI and gender executive orders that any confusion about their scope should be cleared up through “legal advice.” She said Trump’s orders don’t “rise or fall” on whether he adequately explained their reach.
The unprecedented nature of the Trump administration’s sweeping actions so far makes it hard to glean any lessons from history on how to wage legal battles against it, Zick said.
“Except that presidents have prevailed in some and lost in other tough cases,” he noted. “I suspect that will be Trump’s experience too.”
