In a courtroom twist that reads more like a scathing editorial than a typical legal decision, a federal judge didn’t just strike down one of Donald Trump’s executive orders—he obliterated it, exclamation points and all.
The target? An executive order that tried to strip certain major law firms of their government security clearances and block their access to federal contracts, all because they’d previously worked with Trump’s political opponents.
And the judge’s message was crystal clear: This isn’t how democracy works.
The Executive Order That Sparked a Legal Firestorm
Back in March, former President Trump issued a batch of executive orders that were immediately seen as controversial.
These directives restricted law firms like WilmerHale from entering government buildings, working with federal agencies, and bidding on government contracts.
Why? Because some of these firms had represented people or groups that Trump didn’t particularly like—legally or politically.
For WilmerHale, that meant getting targeted for once employing Robert Mueller, the special counsel who investigated Trump’s ties to Russia.
Judge Leon Delivers a Fiery 73-Page Rebuke
On Tuesday, U.S. District Judge Richard Leon—appointed by President George W. Bush—delivered his ruling: the executive order was completely unconstitutional.
And he didn’t just say it; he shouted it with over two dozen exclamation points scattered throughout his opinion.
Leon emphasized that the independence of the legal profession is a bedrock of American democracy, writing, “The cornerstone of the American system of justice is an independent judiciary and an independent bar willing to tackle unpopular cases, however daunting.
The Founding Fathers knew this!”
“That Dog Won’t Hunt!”—Judge Calls Out Trump’s Arguments
Judge Leon didn’t just strike down the order; he dismantled the Trump administration’s legal reasoning with colorful language you rarely see in court filings.
When government lawyers argued that WilmerHale hadn’t shown concrete harm, Leon scoffed: “Please – that dog won’t hunt!” He also dismissed the idea of delaying relief until agencies could figure out how to handle the clearance issue, replying simply: “Please!”
He slammed the executive order as a form of retaliation—a way of punishing law firms for taking on clients or causes Trump disagreed with.
According to Leon, that’s viewpoint discrimination, and it violates the First Amendment.
The First and Fifth Amendments Both Violated
Judge Leon wasn’t done. He also found that the order violated the Fifth Amendment by being overly vague and infringing on the firm’s right to counsel.
The sweeping nature of the restrictions, he said, was designed to make clients drop WilmerHale out of fear—and that was unconstitutional.
He called the sanctions “a staggering punishment for the firm’s protected free speech,” adding, “This Order is intended to and does, in fact, impede the firm’s ability to effectively represent its clients!”
WilmerHale Celebrates a Constitutional Win
Naturally, WilmerHale was quick to applaud the decision.
In a statement released Tuesday, the firm said, “The Court’s decision to permanently block the unlawful executive order in its entirety strongly affirms our foundational constitutional rights and those of our clients.
We remain proud to defend our firm, our people, and our clients.”
Other Judges Are Also Siding Against Trump
This isn’t the first ruling against Trump’s orders targeting law firms.
Just last Friday, another federal judge, John Bates, struck down a similar order against Jenner & Block, calling it an attempt to “chill legal representation the administration doesn’t like.”
Earlier in May, Judge Beryl Howell rejected a separate order aimed at Perkins Coie, quoting Shakespeare in her opinion: “The first thing we do, let’s kill all the lawyers.”
The Broader Legal Fallout—and a Billion-Dollar “Settlement”
Meanwhile, other top law firms are choosing to quietly settle rather than face Trump’s wrath.
Several firms have reportedly agreed to provide hundreds of millions of dollars in pro bono legal services to causes Trump supports—veterans, military families, law enforcement, and others.
According to Trump, these settlements are adding up: “They give me a lot of money considering they’ve done nothing wrong,” he said on Truth Social.
He estimated that about $1 billion in legal value has been pledged so far.
What’s Next?
Trump has yet to publicly comment on Judge Leon’s ruling, and the Department of Justice hasn’t issued a statement either.
Meanwhile, one more lawsuit—brought by the law firm Susman Godfrey—is still pending in court.
The larger question now looms: Will Trump continue to pursue legal battles with the firms that challenge him? Or will these court rulings mark the end of a strategy that’s already being swatted down as unconstitutional, retaliatory, and legally absurd?
Only time—and more fiery rulings—will tell.