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How Trump is finding workarounds to legal hurdles
Mar 26, 2025
There’s a theme emerging in the Trump administration’s battles in courtrooms across the country contesting an array of executive actions facing litigation.
As the saying goes, if you can’t go under or over — go around.
As judges issue injunctions blocking particular executive ord
ers or policies, the administration has returned to court with a new legal arsenal of laws and authorities to justify their sweeping plans to reshape the federal bureaucracy.
Essentially, they’re learning on the fly — taking lessons from adverse rulings and judges themselves to press on with the president’s agenda.
Take the U.S. Agency for International Development (USAID), for example. As a federal judge ruled last week that Elon Musk and the Department of Government Efficiency (DOGE) likely had no authority to shutter the foreign aid agency from the outside, the administration had a plan B.
The same day, Secretary of State Marco Rubio formally appointed Jeremy Lewin, the USAID DOGE team lead, to become the agency’s chief operating officer. The administration insists this was done before the judge’s order (see Rubio’s signature making it official).
The government argued Lewin is now a “properly named USAID official” and urged the judge to make clear Lewin can take actions at the agency.
U.S. District Judge Theodore Chuang, an appointee of former President Obama overseeing the case, disagreed. He said allowing Lewin in would “undermine” his order, which barred DOGE-affiliated individuals from messing with USAID.
That’s not the only time the Trump administration has seen an opening.
As the administration asserts it did not violate Obama appointee U.S. District Judge James Boasberg’s headline-grabbing order blocking Trump’s invocation of the Alien Enemies Act to carry out swift deportations, the administration acknowledges that one flight destined for El Salvador took off after the judge’s written order issued at 7:25pm ET that Saturday night.
Not to worry, the government says. Unlike the other flights that brought hundreds of Venezuelan migrants to the notorious Salvadoran prison under the centuries-old, wartime law, that final flight was deporting migrants under another law, the administration contends.
Deputy Assistant Attorney General Drew Ensign said Monday during an appeals court argument that the district court’s order applies only to those who would have been deported under the Alien Enemies Act — not those who may separately have final orders.
Even U.S. Circuit Judge Patricia Millett agreed despite repeatedly ripping the administration for treating deportees worse than Nazis removed the last time the government invoked the law.
“That's right,” Millett, an Obama appointee, replied to Ensign.
White House wins have sometimes come from the judges themselves.
During a hearing last month over the revocation of The Associated Press’s White House access, U.S. District Judge Trevor McFadden called it “a little odd” that the White House Correspondents’ Association decides who’s allowed in the pool, a small group of independent journalists at a variety of news organizations who report on the president’s actions.
McFadden at one point said he could “decide to throw out” the group altogether.
Days later, the Department of Justice (DOJ) wrote in court filings the White House’s decision to take control away from the correspondents association on which outlets get to pool the president and the administration’s intent to broaden the group by two additional outlets each day.
But other cases have proven to be lessons hard learned.
The administration has extensively complained about two judges’ rulings ordering that fired probationary workers be rehired at more than a dozen agencies. The administration is taking one of those rulings to the Supreme Court.
The judges have made clear it didn’t have to be this way; the administration merely failed to follow the proper procedures.
“The words that I give you today should not be taken that some wild-and-crazy judge in San Francisco said that an administration cannot engage in a reduction in force,” U.S. District Judge William Alsup, an appointee of former President Clinton, noted as he handed down his ruling.
“It can be done, if it’s done in accordance with the law.”
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Why Barrett, Gorsuch may author 'ghost gun' decision
The Supreme Court has yet to release its highly anticipated decision on the legality of former President Biden’s crackdown on “ghost guns.” But we have some clues as to who may be authoring the opinion.
Every month the court hears arguments, it generally divides the opinions evenly so that each justice writes a majority opinion for one case (when there are nine cases).
For the court’s October session, the justices have announced decisions for seven of the nine cases. That leaves just two justices likely drafting the court’s opinion on ghost guns, Justice Neil Gorsuch and Justice Amy Coney Barrett.
Both are Trump appointees. That doesn’t bode well for defenders of Biden’s crackdown — though, a word of caution: this is not a hard rule and is sometimes not followed.
One recent exception occurred last term, when Justice Samuel Alito did not author a majority opinion for any case argued in March while Justices Clarence Thomas and Sonia Sotomayor both wrote two.
CNN reported that Alito was originally assigned the majority opinion in a Texas city councilwoman’s retaliation lawsuit filed after she was arrested for removing a public document at a meeting. But Alito reportedly couldn’t “hold five” to form a majority, and the court ultimately issued a more limited decision.
This term, the Supreme Court is burning rubber as it hands down opinions at a rapid pace.
So far, the court has released opinions in 17 argued cases. We expect they have 44 opinions remaining.
It’s a jump from this time last term, when the court had released 11 opinions. And the year before that, the court had issued just eight.
Previous terms’ initial sluggishness prompted significant speculation, particularly as to whether new protocols implemented after the leak of the court’s draft abortion opinion was causing delays (justices have denied this).
Whatever the cause, the court has regained speed as its prime decision season fast approaches in May and June.
Just last week, the justices issued two opinions. They ruled against a New York crime family associate in finding crimes committed through inaction can still be violent and sided with a Chicago political scion in his appeal of his corruption conviction, agreeing that a law barring lying to regulators only covers false statements, not misleading ones.
Expect more opinions at 10 a.m. EDT today.
Dissent by firearm demonstration
U.S. Circuit Judge Lawrence VanDyke caused a stir when he dissented from his colleagues who upheld California’s large-capacity magazine ban.
Not for what he said, but how he said it.
VanDyke did not think the written word effectively illustrated his disagreement with the majority, who ruled such magazines aren’t “arms” protected by the Second Amendment.
So, he also linked to an 18-minute firearms demonstration, filmed in his chambers and posted to the court’s YouTube channel.
In the video, the Trump appointee sits robed at a large wooden table, behind him a firearm mounted on the wall under a screen that reads “Ninth Circuit,” the appeals court on which he sits. He then stands to handle various handguns and explain their ins and outs.
Watch the video here.
The judge’s colleagues weren’t too pleased.
U.S. Circuit Judge Marsha Berzon said he “in essence appointed himself as an expert witness” and was bringing in facts outside the record.
“While the facts Judge VanDyke asserts must be ignored, his wildly improper video presentation warrants additional comment, lest the genre proliferate,” Berzon, a Clinton appointee, wrote in a concurring opinion.
But VanDyke pushed back against what he called his colleagues’ “real beef” with his demonstration. (Can’t say we’ve ever heard a federal judge use that description.)
“Most of Judge Berzon’s withering fire, however, is directed at the perception that I’ve made myself a factual expert in this case,” he said. “First, I would be remiss if I didn’t say thank you. But as much as I may be flattered, I think the accusation misses the mark—indeed, I think my colleagues aren’t even aiming at the right target.”
Like VanDyke, other courts are testing new ways to integrate technology into a judiciary that often turns up its nose at efforts to modernize.
The Arizona Supreme Court earlier this month published a YouTube video where a personified artificial intelligence (AI) summarized a recent opinion of the court. The video introduces “Victoria,” the court’s “AI reporter,” who presents the ruling in the style of a news report.
The rhetorical gulch between Biden, Trump's AG's
It’s no surprise that the Justice Department under Attorney General Pam Bondi is already vastly different than under its former leader, Merrick Garland.
But that stretches beyond their policies and into the rhetoric they have used to tout their victories.
Press releases from the attorneys general emphasize the gulch between the leaders, a microcosm of their significantly different approaches to manning the agency. Where Garland’s DOJ took a matter-of-fact approach to its missives, Bondi’s DOJ has taken on a Trumpian slant.
A press release from last week titled “Attorney General Pamela Bondi Announces Severe Charges Against Violent Tesla Arsonists,” details how three individuals “responsible for the violent destruction of Tesla properties” have been charged. Bondi in a statement called the alleged attacks a “wave of domestic terrorism” against billionaire Elon Musk’s electric vehicle company and vowed that DOJ will “put you behind bars.”
Compare that to the Justice Department’s announcement of the seditious conspiracy indictments against Oath Keepers leader Stewart Rhodes and 10 other members of the right-wing extremist group. The charges marked a major inflection point in the Justice Department’s probe of the Capitol attack and Rhodes's eventual conviction would become a crown jewel of the sweeping prosecution.
But the announcement described the Oath Keepers only as a “large but loosely organized collection of individuals, some of whom are associated with militias” and Rhodes as the “founder and leader” of the group. It was littered with descriptors like “charged” and “alleged.” And it included no statement from Garland or any other DOJ official.
Justice Department press releases under Bondi also tend to invoke the president, where Garland’s DOJ sought independence from Biden. She’s also appeared twice alongside Trump just this week – whereas previous presidents tend to distance themselves physically from their appointed DOJ leaders and regularly gives television interviews.
A press release announcing the arrest of an alleged ISIS-K member and planner of the 2021 attack at Abbey Gate, Afghanistan, which resulted in the deaths of several U.S. service members, cited “President Trump’s strong leadership on the world stage” as the impetus of DOJ’s ability to crack down. Bondi called the alleged planner “evil” in the release.
Another release, announcing the dismissal of an environmental justice lawsuit, said in its title that DOJ was “delivering on President Trump’s mandate to end radical DEI programs.”
To be sure, not all press releases are the same. There are plenty of Bondi DOJ announcements that cite “charges” and “allegations” and Garland DOJ pressers condemning bad actors.
But in cases tinged by politics, the politics of the president often seep through.
Petitions Pile
The Supreme Court has not relisted any additional petitions. Check out last week’s edition of The Gavel for a walkthrough of existing relists and come back next week for a preview of the court’s final conference of the March argument session.
In/Out: The Order List
In: Nothing
The court took up no new cases at last week’s conference.
Out: Confrontation Clause, Steve Wynn’s defamation suit
The court declined to take up a case assessing the Constitution’s Confrontation Clause, which provides criminal defendants the right to be confronted with the witnesses against them.
The court had relisted the case six times, and we now know why: Alito and Gorsuch were drafting separate statements.
Alito wrote the court should “reconsider” its 2006 landmark Confrontation Clause precedent, Crawford v. Washington, in an “appropriate case.” But the conservative justice agreed this wasn’t the right vehicle.
Gorsuch echoed similar sentiments, suggesting “we may need to rethink our course sometime soon.”
“Now may not be the moment, I concede, for the Court to take up these questions. The Court issued its latest word on the Confrontation Clause in Smith less than a year ago,” Gorsuch said, referencing a case decided last term.
“Before weighing in again, we may benefit from the insights and further experience of our lower court colleagues,” he continued.
Also, the court declined to revive casino mogul Steve Wynn’s defamation lawsuit against the Associated Press over a story it ran detailing police reports accusing Wynn of sexual misconduct, which he denies.
Wynn asked the court to revisit its 1964 landmark case, New York Times v. Sullivan, that has broadly protected journalists by requiring public officials to show “actual malice” to prove defamation claims.
Wynn is an ally of Trump, who has called for reducing libel protections and has launched several defamation suits against major media companies he views as his enemy.
Interestingly, Thomas, who has repeatedly said the precedent should be overturned, did not publicly dissent or author a written statement.
On the docket
Don’t be surprised if additional hearings are scheduled throughout the week. But here’s what we’re watching for now:
Today
The Supreme Court will announce opinions.
The justices will also hear oral arguments over whether the Universal Service Fund, a reserve of money pooled by telecommunications companies to ensure universal access to communications services, violates the nondelegation doctrine.
A pretrial conference is scheduled in a challenge to Trump’s DEI crackdown by 11 civil servants in the intelligence community who are on DEI-related assignments.
Thursday
A federal judge in Washington, D.C. will hold a preliminary injunction hearing in the Associated Press’s challenge to the revocation of its White House access.
Another federal judge in D.C. will hold a preliminary injunction hearing in a pair of lawsuits brought by anonymous FBI agents who worked on Jan. 6 cases.
A third federal Washington judge will hold a preliminary injunction hearing in a lawsuit brought by eight inspectors general challenging their firings.
Friday
A federal judge in Boston will hold a hearing on injunctive relief in a challenge brought by four anonymous noncitizens with final removal orders to the Department of Homeland Security’s policy seeking to deport them to a third country – a country in which they have no citizenship and are not from.
Monday
The Supreme Court will announce orders.
The justices will hear oral arguments over whether a state violates the First Amendment’s religion clauses by denying a religious organization an otherwise available tax exemption because the organization does not meet the state’s criteria for religious behavior.
The justices will also hear arguments over whether a law regarding the finality of determination applies only to certain habeas filings.
Tuesday
The Supreme Court will consider whether to uphold a law that allows Americans injured by acts of terror to take Palestinian leadership groups to U.S. courts for damages.
A federal judge in Boston will hold a hearing over whether to stay the Department of Homeland Security’s decision to end temporary protected status for Haitians and Venezuelans in a lawsuit brought by four individuals and three immigration organizations.
What we're reading
Reuters’ Nate Raymond: US judge regrets creating bias concerns over call for women lawyers
J. Michael Luttig, a former judge on the U.S. Court of Appeals for the 4th Circuit, in the New York Times: It’s Trump vs. the Courts, and It Won’t End Well for Trump
POLITICO’s Kyle Cheney and Josh Gerstein: Trump wants adverse rulings overturned ASAP. Appeals courts are taking their time.
The 19th's Grace Panetta: Why the Wisconsin Supreme Court race is getting so much attention — and money
The Atlantic's Jeffrey Goldberg: The Trump Administration Accidentally Texted Me Its War Plans
We’ll be back next Wednesday with additional reporting and insights. In the meantime, keep up with our coverage here.
Questions? Tips? Love letters, hate mail, pet pics?
Email us here: elee@thehill.com and zschonfeld@thehill.com. Securely reach us on Signal here: @elee.03 and @zachschonfeld.48
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