Trump vs AmLaws: Judge Says You Can't Cancel the Constitution

How a Federal Court Just Slammed the Brakes on Political Retaliation Disguised as National Security

In a smackdown that was as inevitable as it was necessary, a federal judge just pulled the plug on President Donald Trump’s latest foray into authoritarian cosplay—this time, via an executive order targeting the venerable law firm Jenner & Block. And make no mistake: this wasn’t some obscure administrative scuffle. This was a full-blown constitutional clash with press freedom, legal autonomy, and separation of powers all hanging in the balance.

The punchline? Trump lost. Hard.

In an 80-page opinion that read like a love letter to the First Amendment, U.S. District Judge John D. Bates ruled that Trump’s executive order was a textbook case of unconstitutional retaliation. The order aimed to strip Jenner & Block of its security clearances and bar it from federal contracts, all because the firm had the gall to represent clients and causes that Trump personally disliked.

Translation: “You defended people I don’t like, so now I’ll destroy your business.”

Weaponizing the White House Against Legal Dissent

This particular power play was part of a broader campaign by Trumpworld to punish firms perceived as unfriendly to the MAGA movement. Jenner’s crime? Employing lawyers like Andrew Weissmann, a key figure in the Mueller investigation. Trump’s executive order—more tantrum than policy—attempted to tie Jenner’s work to national security risks, citing the firm’s prior engagements as grounds for disqualification.

Judge Bates wasn’t having it. Not for a second. In his ruling, he wrote that the executive order didn’t even pretend to be neutral—it was, in fact, “an overt attempt to chill the exercise of protected speech and to penalize a private law firm for the content of its advocacy.”

Boom. That’s legalese for “Stop abusing power because someone hurt your feelings.”

Déjà Vu All Over Again: Perkins Coie, WilmerHale, and the Pattern of Petty Payback

If this all sounds familiar, it should. Just weeks ago, another federal judge struck down a nearly identical order targeting Perkins Coie. WilmerHale has also been in the administration’s crosshairs. Trump’s pattern is clear: If a firm helps investigate him, criticize him, or even exists in the same area code as someone who once donated to a Democrat, he wants them blacklisted.

Forget rule of law. This is ruling by grudge.

Legal Representation Is Not Treason—It’s the Whole Damn Point

The most chilling part? This executive order, had it stood, would’ve set a dangerous precedent: If the president doesn’t like who you represent, he can make your firm radioactive.

Let that sink in. If the government can punish you for taking on controversial clients, then we can kiss due process goodbye. What would have been the response if Biden had revoked the security clearances of law firms who represented The Koch brothers or other conservatives? Republicans would be rending their clothes in the streets and protesting daily. Not with Trump.  “If the King Decrees it, it is lawful” has long been the cry of every monarchy and dictatorship.

Legal professionals aren’t supposed to cower under political pressure—they’re supposed to confront it. As Jenner & Block argued in their lawsuit, allowing the executive branch to retaliate against law firms for the cases they take on would “obliterate the independence of the legal profession.”

A Win for the Rule of Law—and for Anyone Who Still Likes the First Amendment

Judge Bates’ ruling doesn’t just protect Jenner & Block. It protects every law firm, from the AmLaw 100 to the solo practitioner working out of a WeWork. It affirms what most of us assumed was already settled law: that representing unpopular clients is not a crime, it’s a cornerstone of democracy.

The First Amendment exists for exactly this reason—to stop politicians from using the machinery of government as a personal revenge cannon. The court’s message was clear: If you want to run a dictatorship, you’re going to have to do it somewhere else. Preferably far away.

Capitulation or Candor?

And yet, amid the celebration of Jenner’s courtroom victory, it’s worth taking a hard look at some of the AmLaw elite who bent the knee. Firms like Skadden and Paul Weiss jumped to offer Trump sweetheart settlements, pro bono support, and overtly off-loaded their DEI programs at the mere hint of an endangering EO. Additionally, heavy-hitters like Kirkland & Ellis and Latham & Watkins—two firms that brand themselves as titans of independence – bent the knee without even being summoned by the king.

Were they capitulating out of fear? Or just showing their true colors? In an industry that loves to talk about ethics, rule of law, and courageous advocacy, their actions speak louder than a hundred mission statements. Old White and Blue Hair found dumping everything that had been fought for since Martin Luther King, all too easy to sweep under the proverbial rug.

The Legal Profession Breathes (and Briefs) Easier

The ruling sends a loud, clear message: Lawyers are not pawns in political vendettas. And law firms are not beholden to presidential approval ratings. As much as some may long for the days of loyalty oaths and blacklists, this isn’t 1950—and even if it were, Jenner & Block would be well within its rights to tell McCarthy to pound sand.

This decision also offers a moment of reassurance to the broader legal community, which has watched in stunned disbelief as political attacks on attorneys have moved from the fringe to the front page. If this is the line in the sand, it couldn’t come soon enough.

What Comes Next: Precedent, Pushback, and a Press Briefing Attacks

Don’t expect Team Trump to take the loss gracefully. Trump never takes any setback with grace and aplomb. The now normal accusations against an overly liberal judge (who was appointed by Bush, btw) will inevitably ensue. But this ruling arms other firms with precedent—and resolve. More importantly, it reminds the judiciary that regardless of the political power plays and press briefings, their independence isn’t just theoretical. It’s enforceable. And enforce it they did.

Final Thoughts: You Can’t Lead a Free Country While Punishing Free Speech

This wasn’t just a legal win—it was a moral one. A First Amendment victory in a time when the president of the United States seems to feel the Constitution is “optional”. When Due Process and judicial orders are ignored by a man who obviously feels their should be no checks & balances. A win against a man who claims on live television that he “doesn’t know” if he’s required to uphold the very document to which he took his oath of office. It wasn’t just the legal profession that needed this one – it was the country.