Washington’s federal courthouse is accustomed to high‑stakes political showdowns, yet the April 30 hearing before U.S. District Judge John D. Bates quickly became a civics lesson in executive power. Bates, a George W. Bush appointee known for meticulous opinions, spent nearly two hours grilling Justice Department attorney Richard Lawson about President Donald Trump’s Executive Order 14246.
The directive brands Jenner & Block a threat to “governmental cohesion” and strips the 110‑year‑old firm of security clearances, federal contracts, and building passes.
“Point me to the statute that lets a president punish a law firm without an individualized finding of wrongdoing,” Bates repeated, unfazed by references to broad national‑security powers. Each answer drew sharper follow‑ups. Observers noted that the question judge questions legality of Trump’s executive order targeting law firm Jenner & Block dominated the courtroom long before reporters typed their headlines. By the session’s end Bates had openly compared the order to shuttering a newspaper for unfavorable coverage—an analogy that previewed the constitutional gauntlet ahead.
Inside the Sweeping Directive
Signed on March 29 2025, Executive Order 14246 commands every federal agency to:
- revoke all security clearances held by Jenner & Block attorneys;
- terminate current contracts and forbid new bids;
- reopen past settlements in which the firm represented parties adverse to the United States.
The White House accuses the firm of “partisan lawfare” and “discriminatory staffing,” but has offered no documentation beyond public briefs Jenner & Block filed challenging Trump‑era immigration rules and climate regulations. Legal historians say no modern president has wielded procurement authority this aggressively against a domestic legal institution; previous contract bans have targeted foreign companies tied to adversary governments, not an American law firm headquartered in Chicago.
Jenner & Block counters that its diversity programs and pro‑bono docket mirror those of countless Big Law peers. The firm’s managing partner, Randy Mehrberg, called the order “an effort to scare lawyers away from representing clients the administration doesn’t like,” adding that such retaliation “strikes at the heart of the adversarial system.”
Constitutional Fault Lines Exposed
The lawsuit Jenner & Block filed on April 15 lays out a triad of constitutional claims:
- First Amendment – The firm argues the order punishes attorneys for the clients they represent, thereby chilling speech and association.
- Fifth Amendment – By revoking clearances and contracts without notice or a hearing, the directive allegedly deprives lawyers of property interests without due process.
- Separation of Powers – By hamstringing advocates who challenge executive actions, the order purportedly insulates the president from judicial scrutiny.
During the April 30 hearing, Bates echoed these themes. He noted that national‑security restrictions normally require individualized findings, not a blanket ban on an entire organization. Pressing Lawson, he asked whether the government could similarly target WilmerHale or Perkins Coie—two other firms that have sued over parallel orders—simply for “taking on the wrong client.” The exchange underscored the stakes: if the directive survives, future presidents could pressure lawyers, journalists, and nonprofits through contracting power alone.
Stakes for the Legal Industry
That prospect already alarms the bar. Since March, four powerhouse firms—WilmerHale, Perkins Coie, Susman Godfrey, and Skadden—have either filed companion suits or negotiated costly pro‑bono concessions, collectively pledging nearly $400 million in free legal services to stay off the administration’s radar. Industry analysts estimate more than $2 billion in annual revenue and thousands of high‑security legal jobs hang in the balance.
Bar associations warn of a chilling effect: firms may refuse politically sensitive representations to preserve clearances and federal work. Law‑school deans worry recruits will shun public‑interest litigation if it jeopardizes future government service. Corporate clients, meanwhile, fear their counsel could vanish mid‑case should the White House disapprove of a legal position. As one general counsel put it, “If your lawyer can be sidelined by tweet, you start rethinking every lawsuit you file.”
The Road Ahead
Bates promised a written opinion “in short order.” Should he grant Jenner & Block’s motion for a preliminary injunction, the Justice Department will race to the U.S. Court of Appeals for the D.C. Circuit, where related appeals from WilmerHale and Perkins Coie wait in the wings. A rapid petition to the Supreme Court is likely if lower‑court rulings diverge, particularly because the government couches its rationale in national security.
Capitol Hill is also watching. Bipartisan bills introduced in both chambers would bar any president from blacklisting contractors absent a public, evidence‑based finding vetted by inspectors general. Sponsors cite the Jenner & Block controversy as proof that “unchecked executive procurement power is a loaded weapon pointed at the rule of law.”
For now, the firm operates under a temporary restraining order that blocks immediate enforcement, but partners say uncertainty still looms. Prospective recruits ask whether they’ll ever obtain clearances. Existing clients demand written assurances that representation will not trigger government retaliation.
Whatever Bates decides, one question will reverberate: Can a president wield the federal checkbook to silence courtroom adversaries? The answer will define the outer boundary of executive power—and the independence of America’s legal profession—for years. Until then, every brief, filing, and headline repeating judge questions legality of Trump’s executive order targeting law firm Jenner & Block keeps the stakes vivid for the bench, the bar, and the public.