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Trump and His Big Law Firms Keep Losing
As Trump’s courtroom defeats pile up, the Big Law firms that settled face new uncertainties about their attorneys, their clients, and their futures.
May 27, 2025
President Donald Trump and the Big Law firms that surrendered to his unconstitutional executive orders suffered another bad week.
Trump Loses Again
In a 52-page opinion, U.S. District Court Judge John D. Bates—a 2001 appointee of President George W. Bush—rejected the Justice Department’s effort to defend Trump’s executive order targeting Jenner & Block. Trump’s own words doomed it:
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. (Jenner & Block v. U.S. Department of Justice, et al. Civil Action No. 25-916 (JDB) p. 1)
The court left no doubt that Trump had violated the Constitution:
Going after law firms in this way is doubly violative of the Constitution. Most obviously, retaliating against firms for the views embodied in their legal work—and thereby seeking to muzzle them going forward—violates the First Amendment’s central command that government may not “use the power of the State to punish or suppress disfavored expression.” (Id.; citations omitted.)
Describing how Trump’s actions undermine democracy, Judge Bates previewed the fate awaiting similar orders:
This order, like the others, seeks to chill legal representation the administration doesn’t like, thereby insulating the Executive Branch from the judicial check fundamental to the separation of powers. It thus violates the Constitution and the Court will enjoin its operation in full. (Id.; emphasis supplied.)
The firms that challenged Trump remain undefeated in the courtroom.
Big Law Firms That Settled Lost Again
Judge Bates sent a message to firms that settled: They should not have “bowed” to Trump. (Id. at p. 1). Calling out the first firm to settle—Paul, Weiss, Wharton, Rifkin, & Garrison—the court seemed incredulous that “[o]ther firms skipped straight to negotiations. Without ever receiving an executive order, these firms preemptively bargained with the administration and struck deals sparing them.” But the firms that settled merely created worse problems for themselves:
“A firm fearing or laboring under an order like this one feels pressure to avoid arguments and clients the administration disdains in the hope of escaping government-imposed disabilities. Meanwhile, a firm that has acceded to the administration’s demands by cutting a deal feels the same pressure to retain “the President’s ongoing approval.“ Either way, the order pits firms’ “loyal[ty] to client interests“ against a competing interest in pleasing the President. (Id. at p. 16; citations omitted.)
Urging that “‘[t]he right to sue and defend in the courts’” is “‘the right conservative of all other rights, and lies at the foundation of orderly government,’” Judge Bates continued:
Our society has entrusted lawyers with something of a monopoly on the exercise of this foundational right—on translating real-world harm into courtroom argument. Sometimes they live up to that trust; sometimes they don’t. (Id. at p. 17; emphasis supplied.)
The firms that settled blew it.
The Losses Mount in Other Ways
As they take a well-deserved public beating, the settling firms also produced new and enduring sources of internal instability. In early May, Paul Weiss partner and former Homeland Security Secretary Jeh Johnson announced his retirement to become co-chair of Columbia University’s Board of Trustees. Johnson’s departure followed the exit of Steven Banks, the firm’s pro bono practice leader.
On the same day that Judge Bates issued his opinion, litigation department co-chair Karen Dunn and three prominent Paul Weiss partners—Bill Isaacson, Jeanine Rhee, and Jessica Phillips—left to form a new firm. Dunn had assisted former presidential nominee Kamala Harris with debate preparation. Isaacson is one of the country’s leading antitrust lawyers. Rhee was former deputy assistant attorney general at the Office of Legal Counsel under President Barack Obama. Phillips was a former clerk for U.S. Supreme Court Justice Samuel Alito. Their new firm will operate free of Paul Weiss’ restrictive settlement terms.
Among those restrictive terms are mandatory pro bono legal services to Trump-approved causes. Paul Weiss, Skadden Arps, Kirkland, & Ellis and other settling firms are fielding such requests and generating unwanted publicity.
Conservative Newsmax host Greta Van Susteren pressed Skadden to represent a veteran wanting to sue a Michigan judge who had issued a protective order against him in a divorce. When the firm equivocated, Van Susteren blasted Skadden on X, where she has more than one million followers. The New York Times covered the episode on the front page of its May 26, 2025 print edition.
It could get worse. Trump’s April 28 executive order requires Attorney General Pam Bondi to use Big Law pro bono legal services in defending law enforcement officials accused of civil rights violations and other misconduct.
The “Trump Effect”
Let’s summarize the damage so far:
First, Trump’s courtroom defeats will continue; appellate judges will affirm those rulings; and the U.S. Supreme Court won’t bail him out this time. But he won the things he wanted most: neutralizing powerful potential courtroom adversaries, a $1 billion war chest, and a stunning public relations victory over powerful institutions that could have slowed his drive toward autocracy—all thanks to the firms that capitulated.
Second, government attorneys trying to save Trump’s unconstitutional orders are suffering irreparable career damage to their reputations. They’re losing credibility defending the indefensible with specious arguments and abandoning their sworn obligations to uphold the Constitution and the rule of law.
Finally, the Big Law firms that settled face new uncertainties about their attorneys, their clients, and their futures. They could admit their monumental mistakes, cut their losses, and walk away from a bad deal that is becoming worse by the day. But that would require humility, sound judgment, and a spine.
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Trump Lawyers Behaving Badly
The White House attorneys who drafted Trump’s executive orders targeting Big Law firms—and the Justice Department lawyers trying to defend them—should consider the oath they took to defend the Constitution.
May 04, 2025
U.S. President Donald Trump directed Attorney General Pam Bondi “to seek sanctions against attorneys and law firms who engage in frivolous, unreasonable, and vexatious litigation,” including legal filings for improper purposes and statements that are not based on evidence.
Bondi should start with the White House attorneys who drafted Trump’s executive orders targeting Big Law firms—and her Justice Department lawyers trying to defend them.
Did Real Lawyers Write These Orders?
Cloaked in empty rhetoric about “conduct detrimental to critical American interests,” retribution is at the core of Trump’s edicts.
For example, the only detailed rationale for Trump’s Jenner & Block order was the firm’s association with Andrew Weissmann, who returned to the firm in 2020 after completing his work for Special Counsel Robert Mueller on the Trump-Russia investigation. Other than the Weissmann diatribe, Trump’s order merely recited vague and unsupported assertions about alleged “partisan ‘lawfare,’” “abuse of its pro bono practice,” and “racial discrimination.”
But on that basis, Trump directed all federal agencies to: 1) limit the entire firm’s engagement with federal employees; 2) limit the entire firm’s access to federal buildings; 3) suspend the entire firm’s security clearances; 4) terminate the firm’s government contracts; and 5) require all government contractors to disclose any business that they do with Jenner—with an eye toward terminating those contracts as well.
Zealous advocacy on behalf of any client—even the president of the United States—has limits.
Four law firms have challenged Trump’s similar orders. In stark language, four separate federal courts have granted immediate relief:
- “Disturbing”
- “It sends little chills down my spine.”
- “It threatens to significantly undermine our entire legal system and the ability of all people to access justice.”
- “There is no doubt this retaliatory action chills speech and legal advocacy, or that it qualifies as a constitutional harm.”
- “The framers of our Constitution would see this as a shocking abuse of power.”
In three recent hearings, Deputy Associate Attorney General Richard Lawson—Bondi’s longtime Florida colleague and Trump loyalist—struggled to answer judges’ basic questions about the orders targeting Perkins Coie, WilmerHale, and Jenner & Block:
- Do law firms have to make deals with Trump to avoid executive orders?
- “I can’t speak to that.”
- Are the deals in writing?
- “I have not been privy to this.”
- Has Trump achieved $1 billion in deals yet?
- “I do not know.”
When Lawson argued that Trump could target Jenner because it “discriminates against its employees based on race,” U.S. District Court Judge John Bates, an appointee of President George W. Bush, snapped back, “Give me a break.”
In fairness to Lawson, Trump and his White House attorneys who wrote the orders hadn’t given him much to work with.
Jenner: A Case Study
Take a closer look at Jenner’s claims, followed by selected highlights of the government’s 37-page response:
The First Amendment:
- Prohibits retaliatory actions for protected speech and viewpoint discrimination;
- Bars government interference with a client’s right to associate; and
- Prevents the government from imposing unconstitutional conditions on access to government services and benefits.
The government says that Trump was just exercising his free speech rights. It asserts that Jenner’s lawsuit “carries with it a dangerous risk of muzzling the Executive.” The government also argues that Jenner’s speech is not protected insofar as it “consists of employment practices involving racial discrimination [favoring women and minorities].”
The Fifth and Sixth Amendments guarantee a litigant the unfettered right to the effective assistance of counsel of his or her choice.
The government says that: 1) clients (not law firms) have to assert such claims; 2) any impact of barring Jenner from federal buildings or its clients from federal contracts is speculative; and 3) Trump’s order does not violate those rights in any event.
Due Process is required before the government can deprive a person of liberty or property interests. It requires notice of the claims, clarity about their meaning, and the opportunity to be heard before the deprivation occurs. None of that occurred. The resulting harm, including damage to the firm’s reputation, was immediate and ongoing.
The government says that: 1) the order is sufficiently clear; 2) it has not yet harmed the firm; and 3) the firm will receive any required notice before the order actually injures it.
Equal Protection requires the government to treat similarly-situated entities similarly or, at a minimum, have a rational basis for failing to do so.
The government insists that Jenner is not being singled out for unfair treatment.
The Constitution’s Separation of Powers prohibits Trump from acting as accuser, prosecutor, judge, jury, and executioner. But he wore all of those hats in his executive order.
The government says that Trump’s order is an appropriate exercise of presidential power.
Attention All Trump Lawyers: It’s Time for a Gut Check
Zealous advocacy on behalf of any client—even the president of the United States—has limits. Upon admission to the bar, every attorney swears an oath to defend the U.S. Constitution and to uphold the rule of law. A code of professional ethics requires any legal argument to be “warranted by existing law or by a nonfrivolous argument” for changing it. Attorneys must ensure that their statements about facts are “reasonably based” on evidentiary support.
Trump’s retaliatory orders seek to intimidate lawyers and law firms into submission and thereby undermine the legal system. His own conduct refutes his lawyers’ contrary arguments. As other firms have capitulated, pledged “political neutrality,” and collectively committed to provide almost $1 billion in free legal services to Trump-designated causes, his executive orders’ stated concerns about those firms’ “conduct detrimental to critical American interests” miraculously disappeared.
Trump even boasted, “And I agree they’ve done nothing wrong. But what the hell—they give me a lot of money, considering.”
In one of the many amicus briefs supporting Jenner’s challenge, more than 800 law firms—including Deputy Associate Attorney General Lawson’s former firm, Manatt, Phelps, & Phillips—urged that Trump’s executive order “should be permanently enjoined as a violation of core First, Fifth, and Sixth Amendment guarantees, as well as bedrock separation-of-powers principles.”
“But something even more fundamental is at stake… [Trump’s] Orders pose a grave threat to our system of constitutional governance and to the rule of law itself.”
I don’t know what Trump’s lawyers see when they look into a mirror. But I know this: History will not be kind to them.
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A Nation of Laws, Not Men: Why Lawyers Are Taking a Stand This Law Day
The oath we took upon joining the bar wasn't a one-time ceremony but a lifelong commitment. On May 1, we renew our promise to the Constitution en masse.
Apr 30, 2025
The American promise rests on a profound yet simple idea: We are governed by laws, not by the whims of individuals. This bedrock principle—that impartial rules apply equally to all—faces an unprecedented assault. On May 1, state and local bar associations, civil rights organizations, and lawyers nationwide will unite in an unprecedented mobilization to defend this cornerstone of American justice.
As lawyers, we take a solemn oath: to support the Constitution of the United States. "Support" in this context implies a more proactive stance than mere defense. This oath compels us to take affirmative steps to uphold the principle that law, not personal power, reigns supreme. Today, fulfilling this obligation has never been more critical.
This Thursday, lawyers in over 40 cities will stand shoulder to shoulder, collectively raising their right hands to publicly recommit to their sacred oath for the National Law Day of Action. This act isn't mere symbolism—it's an alarm bell in a moment of genuine peril for our justice system.
Our message is simple but urgent: If we allow the independence of courts and lawyers to be compromised today, our other rights will become negotiable tomorrow.
The threats to judicial independence have become impossible to ignore. When a federal judge faces impeachment threats simply for upholding the law—as Judge James Boasberg did after halting deportation flights—we've crossed a dangerous threshold. We've witnessed instances where judicial directives are contested not through proper legal channels but through public disparagement and apparent noncompliance. Alarmingly, the arrest of Milwaukee County Circuit Judge Hannah Dugan by federal authorities represents an unprecedented escalation, sending a chilling message to judges across the country. When court orders are treated as optional suggestions rather than binding mandates, and when attorneys face intimidation for representing unpopular clients, our constitutional foundations are actively eroding.
A nation of laws requires an independent judiciary. Judges must be able to rule based on law rather than political pressure. Lawyers must be free to zealously advocate without fear of retribution. Without these, equal justice becomes hollow rhetoric. This is starkly illustrated by recent events where law firms representing clients who oppose administration policies have faced executive orders suspending their employees' security clearances and barring them from federal buildings—actions that one judge noted send "chills down my spine" for the "extraordinary power" they represent.
Our judges and courts have no militias. As Alexander Hamilton warned in Federalist 78, courts depend entirely on their institutional legitimacy and the bar's commitment to uphold their authority. When that authority is undermined through defiance or delegitimized through partisan attacks, we approach a system where power, not principle, determines outcomes. A judge intimidated today means justice denied tomorrow.
This national mobilization on Law Day transcends partisan divides because the rule of law transcends politics. We all lose in a system where legal outcomes depend on who holds power rather than what the law requires. The growing pattern of attempts to circumvent judicial authority—from ignoring court orders to demanding recusal after unfavorable rulings to demonizing "activist" judges—represents an assault on constitutional safeguards that protect us all.
The attacks on judges and lawyers form a two-pronged assault on the constitutional order we pledged to defend. An intimidated bar cannot check government overreach; a weakened judiciary cannot enforce accountability. These essential guardians of liberty now face unprecedented threats.
The oath we took upon joining the bar wasn't a one-time ceremony but a lifelong commitment. On May 1, we renew our promise to the Constitution en masse. We will be a visible reminder that the legal profession stands united against forces that would replace the rule of law with the rule of the powerful.
Our message is simple but urgent: If we allow the independence of courts and lawyers to be compromised today, our other rights will become negotiable tomorrow. No freedom survives when those who defend it are silenced or controlled.
We call on every member of the bar—and indeed every person who values constitutional government—to join this historic stand for democracy. Find your local event at LawDayofAction.org. When we stand together, recommitting to our oath with one voice, we send an unmistakable message: The legal profession will defend our nation of laws and ensure justice remains equal for all.
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