Judges on Trump's war on Big Law: 5 explosive quotes from recent orders

Business Insider

29-05-2025

President Donald Trump's recent string of court losses in his war on Big Law has resulted in sweeping smackdowns from federal judges.
The judges, all sitting in the US District Court for Washington, DC, ruled against the Trump administration and blocked executive orders targeting WilmerHale, Jenner & Block, and Perkins Coie.
A decision is still pending in a fourth lawsuit brought by Susman Godfrey over an order targeting the firm.
Nine other law firms have struck deals with Trump, promising a collective near-$1 billion in pro bono work toward his political priorities while averting a punitive executive order.
But the deal struck with Paul Weiss — the first firm to reach an agreement, resulting in a rolled-back executive order — may have backfired on the Trump administration.
In ruling after ruling, judges cite the Paul Weiss affair as an example of how Trump's purported "national security" justifications for his executive orders never made any sense.
Here are the five sharpest takedowns from judges in the Big Law fight.
1. 'Kill all the lawyers'
Coming out of the gate with the first summary judgment decision, US District Judge Beryl Howell compared Trump's executive order targeting Perkins Coie to a quote from William Shakespeare's "Henry VI."
"In a cringe-worthy twist on the theatrical phrase 'Let's kill all the lawyers,' EO 14230 takes the approach of 'Let's kill the lawyers I don't like,' sending the clear message: lawyers must stick to the party line, or else," Howell wrote.
Trump's executive order, Howell said, was meant to disarm a law firm that might challenge his power.
"When Shakespeare's character, a rebel leader intent on becoming king, hears this suggestion, he promptly incorporates this tactic as part of his plan to assume power, leading in the same scene to the rebel leader demanding '[a]way with him,' referring to an educated clerk, who 'can make obligations and write court hand,'" Howell wrote. "Eliminating lawyers as the guardians of the rule of law removes a major impediment to the path to more power."
2. 'Going after law firms in this way is doubly violative of the Constitution'
In an order protecting Jenner & Block, US District Judge John Bates wrote that Trump's order violated the US Constitution in two ways: It violated the First Amendment by using "the power of the State to punish or suppress disfavored expression," and it sought to undermine the courts.
"Going after law firms in this way is doubly violative of the Constitution," Bates wrote.
The "more pernicious" message of Trump's order was to prevent lawyers from protecting people against "governmental viewpoint becoming government-imposed orthodoxy," according to Bates.
"This order, like the others, seeks to chill legal representation the administration doesn't like, thereby insulating the Executive Branch from the judicial check fundamental to the separation of powers," he wrote.
3. "Take a look at the Paul Weiss saga"
Like the other judges, Bates pointed to Trump backtracking his executive order targeting Paul Weiss as evidence that his legal justifications for executive orders targeting other law firms were not sincere.
In each order, Trump has claimed that "national security" issues — which Justice Department lawyers struggled to explain in court filings and hearings — allowed him to issue orders stripping law firm employees of security clearances and cutting them off from government buildings and employees. Bates wrote that the rollback of the order targeting Paul Weiss demonstrated that it was never the real reason behind Trump's order targeting Jenner & Block.
"If any doubt remains as to the sincerity of the invocation of national security, take a look at the Paul Weiss saga," Bates wrote.
"Paul Weiss's executive order imposed the same tailored process on its employees' security clearances," he continued. "What it took to escape that process — denouncing a former partner, changing client selection and hiring practices, and pledging pro bono work to the President's liking — had not even a glancing relationship to national security."
4. "The Founding Fathers knew this!"
US District Judge Richard Leon's exclamation point-ridden order knocking down an executive order targeting WilmerHale quotes from Alexander Hamilton and the Federalist papers about the importance of an independent judiciary.
He wasn't alone — Howell said in her earlier order that John Adams made the unpopular decision to represent British soldiers accused of murder for their roles in the Boston Massacre.
"The cornerstone of the American system of justice is an independent judiciary and an independent bar willing to tackle unpopular cases, however daunting," Leon wrote. "The Founding Fathers knew this!"
Trump's executive orders violated those "fundamental rights," he wrote.
"I have concluded that this Order must be struck down in its entirety as unconstitutional," he wrote. "Indeed, to rule otherwise would be unfaithful to the judgment and vision of the Founding Fathers!"
5. "The Order is akin to a gumbo"
Leon's gumbo metaphor is, once again, a spicy swipe at Paul Weiss.
In arguments leading up to each decision, judges weighed whether to block the entirety of each of Trump's orders or allow some parts to stand.
In a footnote, Leon broke down the five different sections of the WilmerHale order and compared them to gumbo ingredients.
"The Order is akin to a gumbo. Sections 2 through 5 are the meaty ingredients — e.g., the Andouille, the okra, the tomatoes, the crab, the oysters," the judge wrote. "But it is the roux — here, §1 — which holds everything together."
Leon wrote that Trump rescinding Paul Weiss's order "in full" after it struck a deal shows that he intended the orders "to stand or fall as a whole."
"A gumbo is served and eaten with all the ingredients together, and so too must the sections of the Order be addressed together," he wrote.
The judge also made clear that the gumbo is spicy.
"As explained in this Memorandum Opinion, this gumbo gives the Court heartburn," he wrote.