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Big Law Deals With Trump Are Backfiring on Top Firms
The president's bullying was always about intimidation and deterrence. Here's the sound it makes when not one, but many, other shoes begin to drop.
May 15, 2025
The Big Law firms that capitulated to President Donald Trump’s unconstitutional demands thought they were buying peace with his administration, preserving their client relationships, and protecting their bottom lines.
Recent developments illustrate the growing magnitude of their mistake.
Fighters Are Winning
On May 2, U.S. District Court Judge Beryl Howell became the first court to issue a final ruling that Trump’s executive orders targeting Big Law firms violated the First, Fifth, and Sixth Amendments to the U.S. Constitution. In a 102-page opinion, the court shredded Trump’s edict with a straightforward analysis that other courts are likely to follow:
“In a cringe-worthy twist on the theatrical phrase ‘Let’s kill all the lawyers,’ [Trump’s Executive Order] takes the approach of “Let’s kill the lawyers I don’t like,” sending the clear message: lawyers must stick to the party line, or else.
“Using the powers of the federal government to target lawyers for their representation of clients and avowed progressive employment policies in an overt attempt to suppress and punish certain viewpoints, however, is contrary to the Constitution,…. Simply put, government officials ‘cannot . . . use the power of the State to punish or suppress disfavored expression.’
“That, however, is exactly what is happening here.”
For those keeping score, Trump’s Justice Department has now lost every courtroom fight on the subject. Jenner & Block, WilmerHale, and Susman Godfrey obtained immediate temporary relief from his executive orders, as did Perkins Coie, which has now won a permanent injunction from Judge Howell.
Meanwhile, how are the firms that caved to Trump doing?
The Other Shoe Drops: #1
After providing Trump with a war chest totaling almost $1 billion in free legal services, the settling firms are now learning how he plans to use it. Previously, Trump had mused about using Big Law attorneys on coal leasing and tariff deals, but on April 28 things got real.
Trump issued an executive order titled, “STRENGTHENING AND UNLEASHING AMERICA’S LAW ENFORCEMENT TO PURSUE CRIMINALS AND PROTECT INNOCENT CITIZENS.”
The order emphasized the need to “protect and defend law enforcement officers wrongly accused and abused by State or local officials.” It directed Attorney General Pam Bondi to provide the legal resources necessary to defend those officers, including “private-sector pro bono assistance.” [emphasis supplied]
Stated simply, police officers accused of brutality and other misconduct will get Big Law attorneys to defend them – free of charge.
Meanwhile, traditional pro bono causes, including defending immigrants’ rights, are suffering from the deterrent effect of Trump’s attack. Fearing his wrath, they are declining work that challenges his policies.
Settling firms were already getting blowback from their partners and associates as many have left their firms. Trump’s newly-added page to their pro bono catalog won’t help recruiting or retention. And as with all things Trump, there’s no limiting principle. Appeasement never produces finality.
The Other Shoe Drops: #2
The firms’ stated reason for capitulating to Trump was concern that clients would leave any firm that was not in Trump’s good graces. That premise is not aging well either.
On April 11, Simpson, Thacher & Bartlett agreed to provide $125 million in pro bono work “and other free legal services” to Trump-designated causes.
On April 22, the firm informed the Delaware Chancery Court that it would no longer be representing Microsoft in a case related to its 2023 acquisition of Activision. The same day, Jenner & Block replaced Simpson Thacher as Microsoft’s counsel.
Losing a client to another firm is not uncommon, and none of the players has commented on Microsoft’s switch. But capitulation to Trump has not been a panacea for preserving client relationships. A firm that challenges an unconstitutional order threatening its existence is a firm that many clients want fighting for them.
The Other Shoe Drops: #3
On April 24, 16 House members sent letters to nine firms that settled with Trump. Asking about their motivations and urging them to disavow the deals, lawmakers suggested that the agreements may violate federal and state criminal and civil laws while creating “potentially irresolvable violations of applicable Rules of Professional Conduct.” Previously, Sen. Richard Blumenthal (D-Conn.) and Rep. Jamie Raskin (D-Md.) sent requests for information from several firms and White House counsel on April 6 and April 18.
The Other Show Drops: #4
Firms assumed that capitulation would occupy a single news cycle and then disappear. But their public relations nightmares aren’t going away. Apart from the widespread and ongoing condemnation of the legal community, the story continues to have legs as a fateful moment for the rule of law in the United States.
The May 4 edition of CBS’s 60 Minutes ran a damning segment on Big Law firms that settled with Trump. None was willing to appear and defend itself or its deal. The legal term for such continuing cowardice is res ipsa loquitur – the thing speaks for itself. In this case, the firms didn’t speak at all.
On May 9, an article that later appeared in the New York Times Sunday print edition ran with this headline and subhead:
Can Elite Lawyers Be Persuaded to ‘Wake Up and Stand Up’?
When the law firm Paul Weiss cut a deal with the Trump administration, a new kind of activist emerged.
Some of the settling firms, including Kirkland & Ellis and at least one other, have an escape hatch: Their “handshake deals” with Trump are not in writing. They can do what Trump does when he no longer likes his own prior agreement: Walk away.
In fact, even firms with a written agreement can walk away too. Whatever their form, the deals are probably not enforceable. But that was never Trump’s main objective. It was always about intimidation and deterrence. When firms bent the knee to him, he won and scored an invaluable public relations victory.
And his accompanying billion-dollar windfall didn’t hurt.
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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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Making Big Money But Losing Your Soul: The Shame of the Legal Titans
Every lawyer takes an oath to defend the U.S. Constitution. To abandon that pledge at this moment, when the Constitution is in mortal danger, is shameful.
Apr 11, 2025
As part of U.S. President Donald Trump’s seemingly endless journey on the Good Ship Retribution, he has, as widely reported, now fired shots across the bow of a number of law firms. Their “crime” has been having the audacity to employ lawyers Trump dislikes or representing people or causes he dislikes. The sanctions he wants to enforce are significant, including barring the offending firms’ attorneys from receiving federal contracts, striping them of security clearances, and even barring them from entering federal buildings. And this is in addition to launching federal investigations into their DEI policies.
Because, after all, what could be worse than diversity, equity, and inclusion?
The law firms Trump is attacking are, at least mostly, huge operations, the type of firms that are collectively known as “Big Law.” While some of these firms are fighting back, many have chosen to cut a deal. In other words, they’ve caved. Large firms that have folded include Milbank, Paul Weiss, Skadden Arps, and Willkie Farr & Gallagher. The “honor” of being regarded as the leader of the pack, however, goes to Paul Weiss, as the first to cave.
While earning a living is important, being a lawyer is about much more than money.
As an attorney practicing in a small law firm in Wichita, Kansas, I have little in common with lawyers working in Big Law firms. A Paul Weiss lawyer and I are both attorneys, but we practice in different worlds. For 40 years I have defended healthcare providers in malpractice cases. These lawsuits sometimes involve millions of dollars. That’s chicken feed to these guys. The top Big Law litigators will at times handle litigation involving hundreds of millions of dollars or even more, while, at the same time, the firm’s business lawyers represent corporations in transactions involving multiple billions of dollars.
These Big Law firms are immense. Paul Weiss has over 1,000 lawyers.
My firm has six, and that includes one who is basically retired.
Top partners in Big Law firms like Paul Weiss can charge $2,400 an hour or more.
My usual billing rate is less than a tenth of that number.
The annual pay last year for an equity partner in Paul Weiss was $7.5 million.
My pay is, shall we say, somewhat lower.
A true multinational firm, Paul Weiss has offices located from Asia to Europe and their home base in North America, with offices in both the U.S. and Canada.
My firm has just the one office and none of us have practiced law outside the United States. But I have visited Canada a few times.
I do, however, have one thing in common with Big Law attorneys. We all took the same oath to support and defend the Constitution which, by definition, includes supporting and defending the Rule of Law.
Very few lawyers specialize in constitutional law or professional ethics. Most of us practice in areas like divorce cases (family law), defending or prosecuting criminal cases (criminal law), trying civil lawsuits (trial lawyers), probating wills (estate practice), and representing corporations in business transactions (business law). Working in these specialized areas of the law there’s little occasion to think deeply about concepts like defending the Constitution. But the oath, and the lawyer’s obligation to follow it, is always there.
Law is a profession, but also a business—and, as they say, the business of business is business—in other words, making money. And there is nothing wrong with this. EMS providers save lives, but they also have bills to pay. The need to pay bills is just as true for lawyers. But while earning a living is important, being a lawyer is about much more than money.
Those leaders of Big Law, still refusing to vigorously defend or even speak out in support of the Rule of Law, need to consider what matters most to them. What they would most want to be remembered for—maximizing profit or defending freedom?
Defending the Constitution when, and if, the need arises must always come first. This is true even when doing so is painful, which at times it can be. As a publication of the American Bar Association has said, lawyers “are obligated to act in support of the U.S. Constitution in all situations, especially where it’s the hardest for you.”
Many lawyers have gone through an entire career never having to face an issue like this. But those of us practicing today aren’t that lucky. We live in a time when the survival of the Constitution and the Rule of Law are in the greatest jeopardy since the Civil War. The American people decided to give the staggering power of the presidency to a man who has never tried to conceal his hunger for absolute power, nor his love of cruelty.
Making matters worse, the separation of powers, which is supposed to protect us from presidential overreach, has, in the words of Don McLean, caught the first train to the coast. Congress is moribund. The Supreme Court hasn’t clearly spoken yet. There is reason for concern, given the majority’s far-right ideology, as to how they will rule when the time comes. And even if the Supreme Court rules against Trump he may refuse to accept it, creating a constitutional crisis.
To be honest, I can live with a constitutional crisis. What scares me more is if there isn’t one. That when the general public is finally forced to face up to Trump’s authoritarian agenda, people will yawn and go about their lives. And why wouldn’t they, given the example set by institutions like Columbia University caving to Trump’s extortion/ And the same goes for much of Big Law—choosing the easy route of ignoring their oath to keep the cash flowing into the firm accounts.
Big Law does have much to lose if they fight. Crossing Trump has the potential of creating a serious crimp in their cash flow. Not only would they be risking government business, but they would face a real risk of losing major corporate clients—their biggest cash cow. Corporations will have no problem recognizing that if they continue to retain lawyers who are on Trump’s enemies list, they will face a significant risk that Trump will sic MAGA on them, which could seriously damage their business. If Columbia University and Big Law are willing to kiss Trump’s ring, can anyone doubt that for-profit corporations will do the same?
So yes, Big Law has much to lose. But realistically we aren’t talking about closing the doors of a firm. The worst-case scenario is probably something like equity partners at Paul Weiss only taking home $4 million a year for a few years instead of $7.5 million. But the fact remains, they took an oath. This is part of the quid pro quo inherent in becoming a lawyer. You are allowed to practice your profession, but to do so you must first take an oath accepting the obligation to support and defend the Constitution. This is a duty all lawyers share, whether they work in big firms, small firms, corporate legal departments, the government, or a nonprofit entity. It’s a big part of what defines us.
To abandon that pledge at this moment, when the Constitution is in mortal danger, is shameful. Those leaders of Big Law, still refusing to vigorously defend or even speak out in support of the Rule of Law, need to consider what matters most to them. What they would most want to be remembered for—maximizing profit or defending freedom?
It shouldn’t be a hard decision.
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