A federal judge in Washington, D.C., has issued a full block on an executive order from President Donald Trump that aimed to penalize the law firm Jenner & Block. The order, signed in late March and titled “Addressing Risks from Jenner & Block,” asserted that the Chicago-based firm had compromised professional ethics, engaged in partisan “lawfare,” and misused its pro bono services to undermine justice and U.S. interests.
In response to the executive order, Jenner & Block filed a 64-page legal complaint, arguing that the order was unconstitutional and seeking a permanent injunction to prevent its enforcement.
U.S. District Judge John D. Bates, an appointee of President George W. Bush, sided with the law firm, granting the requested relief in a 52-page memorandum opinion. The judge’s opinion emphasizes that the central issue revolves around the First Amendment rights of lawyers, particularly the protection against government coercion of opinion, drawing on the precedent set by the 1943 Supreme Court case West Virginia State Board of Education v. Barnette.
“In our constitutional order, few stars are as fixed as the principle that no official ‘can prescribe what shall be orthodox in politics,’” Judge Bates wrote in the opinion’s introduction. “And in our constitutional order, few actors are as central to fixing that star as lawyers.”
Judge Bates directly addressed President Trump’s series of executive orders targeting Jenner & Block and other law 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,” he stated. “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 President Trump’s order was Jenner & Block’s re-hiring of Andrew Weissmann, a former top aide to special counsel Robert Mueller during the investigation into Russian interference in the 2016 election and a vocal critic of President Trump. The executive order labeled Weissmann as “unethical,” dishonest, and accused him of building a career on “weaponized government and abuse of power.” Judge Bates dismissed the focus on Weissmann, noting that he has not been an employee of Jenner & Block since 2021.
“It 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 President Trump, in a signing statement, identified Weissmann as the “main culprit,” the court used this example to illustrate a broader constitutional issue with the executive order. “Jenner’s primary claim — and its most straightforward winner — is the First Amendment retaliation claim,” Judge Bates concluded.
The court examined each section of President Trump’s order, determining that each complaint targeted activity protected by the First Amendment. Judge Bates emphasized that Jenner & Block’s “partisan representations to achieve political ends” constitute courtroom advocacy, which lies at the core of the First Amendment’s protection of “litigation as a vehicle for effective political expression and association.” He also highlighted the pro bono representation of transgender individuals and asylum-seekers as activities protected by the freedoms of speech, petition, or assembly.
“The challenged executive order targets Jenner for what it has said and thereby attempts to dampen what it might yet say,” the judge wrote. “That is unconstitutional under any view of the First Amendment.” Judge Bates noted that this retaliation was not just a backward-looking punishment but appeared intended to dissuade the firm from future pro bono work challenging the government.
The opinion also underscored the crucial interdependence of the judiciary and the bar. “An informed, independent judiciary presumes an informed, independent bar,” Judge Bates stated, emphasizing that limitations on lawyers’ speech must be carefully scrutinized as they threaten not only the lawyers and their clients but also the functioning of a coequal branch of government. He concluded that official attempts to restrict lawyers’ advocacy based on the President’s political preferences pose a significant threat to the constitutional order by seeking to shield the government’s actions from judicial review.
In its assessment, the court was critical of President Trump’s attack on Jenner & Block and other similarly situated law firms. “In short, the order raises constitutional eyebrows many times over,” Judge Bates summarized. “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.’”
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