President Donald Trump pauses as he speaks in the Oval Office of the White House, Tuesday, May 20, 2025, in Washington (AP Photo/Alex Brandon).
A Washington, D.C., judge has fully blocked one of President Donald Trump‘s executive orders targeting disfavored law firms.
In late March, a recent Executive Order was signed by the 45th and 47th presidents, addressing concerns related to the law firm Jenner & Block. The order accuses the Chicago-based firm of straying from ethical standards, supporting partisan legal battles, and misusing their pro bono work to undermine justice and the interests of the United States.
In turn, Jenner filed a 64-page complaint asking the court to permanently enjoin Trump’s executive order as “unconstitutional.”
Now, U.S. District Judge John D. Bates, a George W. Bush appointee, has granted that requested relief in a 52-page memorandum opinion.
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The Executive Order highlights the importance of lawyers and the First Amendment. It emphasizes the constitutional right protecting individuals from the government imposing specific beliefs, drawing from the 1943 Supreme Court case West Virginia State Board of Education v. Barnette.
The introduction of the opinion stresses the enduring principle in our constitutional system that no government official should dictate what political views are acceptable. It also underscores the pivotal role that lawyers play in upholding this fundamental principle.
The judge does not mince words and immediately singles out Trump’s string of orders targeting Jenner and other firms.
“This case arises from one of a series of executive orders targeting law firms that, in one way or another, did not bow to the current presidential administration’s political orthodoxy,” the judge wrote. “Like the others in the series, this order — which takes aim at the global law firm Jenner & Block — makes no bones about why it chose its target: it picked Jenner because of the causes Jenner champions, the clients Jenner represents, and a lawyer Jenner once employed. Going after law firms in this way is doubly violative of the Constitution.”
One specific grievance cited in Trump’s order is how the law firm rehired Andrew Weissmann — the onetime top lieutenant to special counsel Robert Mueller during the investigation into alleged Russian interference in the 2016 presidential election who would go on to become a trenchant Trump critic in the media. Trump accuses Weissmann of being “unethical,” dishonest, and of having built a career “rooted in weaponized government and abuse of power.”
Bates rubbishes the focus on Weissmann — while noting that he is “not a Jenner employee” who has not worked for the firm since 2021.
“[I]t is evidently Weissmann’s criticisms of the President and participation in a legitimate investigation of election interference that drew presidential disdain; and it is Jenner’s erstwhile association with Weissmann that extended that disdain to the firm,” the opinion reads. “But Weissmann’s activity falls easily within the First Amendment’s muscular protection for ‘criticism of government and public officials,’ and that criticism can no more bring Jenner into the administration’s crosshairs than it can bring Weissmann himself into the administration’s crosshairs.”
While Trump, during a signing statement, singled out Weissmann as “the main culprit,” the court uses the Weissmann example as simply indicative of a broader problem with the order.
“Jenner’s primary claim — and its most straightforward winner — is the First Amendment retaliation claim,” Bates writes.
From the opinion, at length:
Begin with an area of significant agreement: of the activity for which Section 1 denounces Jenner, nearly all enjoys robust First Amendment protection. This elementary and unchallenged point need not occupy much space. Jenner’s “partisan representations to achieve political ends,” is another way of saying courtroom advocacy on behalf of its chosen causes — that is, the very core of the First Amendment’s protection of “litigation as a vehicle for effective political expression and association.” The same goes for Jenner’s pro bono representation of transgender people and asylum-seekers. Whether best captured by the “freedom of speech, petition or assembly,” this is precisely the sort of “vigorous advocacy … against governmental intrusion,” that has long “made lawyerdom proud.”
“The challenged executive order targets Jenner for what it has said and thereby attempts to dampen what it might yet say,” the judge goes on. “That is unconstitutional under any view of the First Amendment.”
This retaliation, Bates notes, is not merely backward-looking. Rather, the court observes, the intent appears to be to frighten the firm into performing less pro bono work targeting the government.
“Although retaliation connotes retrospective punishment, its greatest danger lies in its prospective silencing effect,” Bates writes. “That forward-looking threat looms especially large here, not only for other law firms but for Jenner itself. The administration has shown a repeated willingness to haggle, sending the message loud and clear that Jenner can spare itself — if it compromises its speech. So whereas retaliation usually punishes once and moves along, the retaliation here is ongoing and avoidable.”
And, the judge muses, because the unconstitutional retaliation targets lawyers, the impact sends waves through the legal system at large.
Again, the opinion, at length:
Next, there is the interdependence of bench and bar. “An informed, independent judiciary presumes an informed, independent bar.” So limitations on lawyers’ speech must be examined with care, as such limitations threaten not only the lawyers and their clients but also the ability of a coequal branch of government to function. Official attempts to “draw lines around” lawyers’ advocacy and thereby “exclude from litigation those arguments and theories [the President] finds unacceptable but which by their nature are within the province of the courts to consider” threaten a deep and irreparable rift in the constitutional order because they seek “to insulate the Government’s [acts] from judicial inquiry.” When the government draws legal scrutiny, its response must be to defend itself in court, not to intimidate those who would force it to do so.
The court is unforgiving in its assessment of Trump’s attack on Jenner — and other similarly situated law firms.
“In short, the order raises constitutional eyebrows many times over,” Bates sums up. “It punishes and seeks to silence speech ‘at the very center of the First Amendment’; does so via the most ‘egregious form of content discrimination — viewpoint discrimination’; all in an unacceptable attempt to ‘insulate the Government’s laws from judicial inquiry.’”
