The Law Firms That Appeased Trump—and Angered Their Clients
After firms struck deals to avoid punitive executive orders, some big clients decided to take their business elsewhere
By
Erin Mulvaney, Emily Glazer, C. Ryan Barber and Josh Dawsey
June 1, 2025 9:00 pm ET
At a recent luncheon at Cipriani in Midtown Manhattan, a top lawyer for Citadel delivered a message to leaders of some of the country’s biggest law firms. Brooke Cucinella told them that the hedge-fund company likes to work with law firms that aren’t afraid of a fight.
Cucinella, head of litigation and regulatory inquiries at the business headed by Republican megadonor Ken Griffin, made no mention of politics. But some of the lawyers in attendance took her remarks as reference to a controversy that has been roiling the legal industry.
Some of the listed attendees worked for firms that had cut deals with the White House to avoid punitive executive orders by President Trump. Others were at law firms that had gone to court to fight them.
Support for the law firms that didn’t make deals has been growing inside the offices of corporate executives. At least 11 big companies are moving work away from law firms that settled with the administration or are giving—or intend to give—more business to firms that have been targeted but refused to strike deals, according to general counsels at those companies and other people familiar with those decisions.
Among them are technology giant Oracle, investment bank Morgan Stanley, an airline and a pharmaceutical company. Microsoft expressed reservations about working with a firm that struck a deal, and another such firm stopped representing McDonald’s in a case a few months before a scheduled trial.
In interviews, general counsels expressed concern about whether they could trust law firms that struck deals to fight for them in court and in negotiating big deals if they weren’t willing to stand up for themselves against Trump. The general counsel of a manufacturer of medical supplies said that if firms facing White House pressure “don’t have a hard line,” they don’t have any line at all.
Since late February, Trump has issued a half-dozen executive orders that direct agencies to remove law firms’ security clearances, limit access to federal buildings and remove their clients’ government contracts, citing connections between those firms and the president’s enemies. Trump has said many law firms have weaponized the legal system to hamper the work of the administration.
Four firms—Jenner & Block, Perkins Coie, WilmerHale and Susman Godfrey—elected to fight the administration in court.
The leaders of other firms thought such litigation would destabilize their businesses and send clients running for the exits. In March, one of those firms, Paul Weiss, surprised the industry by reaching a deal with the White House to rescind the order in exchange for providing pro bono work for causes supported by the administration.
Eight other firms, including Kirkland & Ellis, Skadden, Simpson Thacher, A&O Shearman, and Latham & Watkins, reached pacts. In total, the capitulating firms, which include some of the industry’s largest and best-known, agreed to provide about $1 billion in pro bono work.
The agreements were supposed to buy peace and allow the firms to move on, but in the weeks since they have caused rifts between partners, alienated some younger associates and created problems with some longtime clients.
Lost trust
Leaders of the firms that struck deals with the White House said they did so in part to protect their clients, who were at risk of losing their government contracts as a result of the White House’s executive orders against the law firms.
Not long after Latham struck a deal in April, the firm’s chair, Richard Trobman, met with Morgan Stanley’s chief legal officer, Eric Grossman, people familiar with the meeting said. Grossman heard him out about the firm’s reasoning for striking a deal and acknowledged that companies have to do what is best for themselves.
Soon after that meeting, Grossman and other Morgan Stanley lawyers communicated to law firms targeted by the White House that hadn’t signed deals that they were looking to give them new business, the people familiar with the meeting said.
Paul Weiss, a 1,200-lawyer firm that works on many big corporate deals, was one of the first law firms targeted by a Trump executive order. The general counsel of one major financial firm said her anxiety grew by the day when Paul Weiss didn’t sue quickly after being hit with the order. When she heard the firm struck a deal with the White House, she said, she felt “physically ill.”
A top legal executive at another company said she called partners at Paul Weiss before it cut its deal to reassure the firm she would remain loyal, even though doing so risked millions in government contracts. She was shocked when the firm chair Brad Karp announced a deal, she said, and her company has plans to move work away from Paul Weiss.
The day after Paul Weiss struck its deal, female general counsels gathered for a conference in Washington. During a panel at the Women’s General Counsel Network event, a lawyer stood up and said her company had taken steps that morning to pull its business from Paul Weiss. The lawyer received thunderous applause.
About two weeks later, McDonald’s told a court that star Paul Weiss lawyer Loretta Lynch was withdrawing as its attorney in a high-profile lawsuit accusing the fast-food giant of discrimination against Black-owned media companies. Lynch, who had served as attorney general under former President Barack Obama, had been involved with the case for several years. It is unusual for companies to shake up representation close to trial.
Karp, Paul Weiss’s chair and a longtime Democratic donor, has said he made a difficult choice that was necessary to save the firm. In an internal memo, he called the executive order an existential crisis, saying the firm risked losing partners and clients if it sued to block the order. He has told others that handling the executive order was more difficult than managing the firm through the coronavirus pandemic.
Firms that struck deals hoped to find solidarity in numbers. The country’s largest firm, Kirkland & Ellis, which had about $9 billion in revenue last year, lobbied its peers to sign deals.
Trump and the law firms have only disclosed limited details about what pro bono work they have agreed to undertake for the administration. General counsels said that makes it hard for companies to know where conflicts of interest might arise. Trump has taken an expansive view about what is required, openly musing about enlisting the firms to help negotiate trade deals or revive the coal industry.
In April, the general counsel of Microsoft, Jon Palmer, discussed with leaders of Latham his concerns about the deal the firm had struck, including how it could affect Latham’s ability to represent Microsoft, especially before the government, according to people familiar with the discussion.
On April 17, Microsoft put its concerns in writing, removing Latham from a list of about a dozen preferred firms that it has vetted to handle outside legal work, according to a document described to the Journal.
About two weeks later, after a series of conversations with Latham’s leaders that addressed concerns about potential conflicts, Microsoft returned the law firm to its list of preferred firms.
“The Latham agreement created concerns about potential conflict of interest issues that could have affected the firm’s ability to represent Microsoft,” Microsoft’s Palmer said in a written statement. Latham’s leaders, he said, “provided the strong assurances we needed to address our concerns.”
The law firms named in this article declined to publicly discuss client matters. Leaders of firms that struck deals said their business have continued to thrive and that they have received calls from clients supportive of the deals. They have said the agreements won’t force them to take on pro bono work that would create conflicts with existing clients.
The firms that chose to sue over executive orders said in court filings that they had fielded calls from anxious clients and lost business because of the orders. Judges have struck down the orders against WilmerHale, Jenner & Block and Perkins Coie, and the order against Susman Godfrey has been temporarily blocked. Judges have said the executive orders amounted to unconstitutional retaliation against the firms.
On a website touting the firm’s lawsuit, Jenner & Block said relenting to the White House would mean “compromising our ability to zealously advocate for all of our clients and capitulating to unconstitutional government coercion, which is simply not in our DNA.”
Some general counsels said they are giving new work to the resisting firms in a show of solidarity.
Internal strife
At Cadwalader, Wickersham & Taft, managing partner Pat Quinn grew emotional when he announced to fellow partners that their firm—the oldest in New York—had reached a deal for peace with the Trump administration. Days later, in a firmwide meeting, Quinn said Cadwalader’s leadership had strongly considered fighting the Trump administration but ultimately elected to reach a deal out of a sense of duty to the firm and its clients, according to people familiar with his remarks.
Emotions have run high inside some firms that struck deals, particularly among younger lawyers. At Skadden, Simpson, Latham and Kirkland, some associates have quit over the deals. One associate leaving Simpson wrote in his departure email, shared on LinkedIn, that he refused to “sleepwalk toward authoritarianism.” Partners, too, have left some of the firms that made deals.
At Sullivan & Cromwell, some lawyers have bristled at the role that co-chair Robert Giuffra played in facilitating a deal for Trump to drop an executive order against rival firm Paul Weiss. Giuffra, one of Trump’s personal lawyers, participated by phone in an Oval Office discussion with the Paul Weiss leader, who was there to work out a deal.
Giuffra is representing Trump in two New York appeals—one of them a challenge to his conviction in the Stormy Daniels hush-money case. Giuffra told his partners that taking on the cases would give the firm strong ties to the new administration.
Trying to quell discontent within his own firm, Giuffra told partners at an April meeting that he believed the orders were likely unconstitutional and would be blocked by judges, and that he hoped the White House would stop issuing them, according to people familiar with his remarks. White House aides said they weren’t aware of his opposition.
Trump remains interested in the orders, and deputy White House chief of staff Stephen Miller and his allies want to keep the threats of more executive orders on the table because they think it dissuades the best lawyers from representing critics of the administration. Miller has repeatedly complained that some of the country’s top lawyers took on lawsuits against the Trump administration in the first term, which he and other Trump advisers view as stymying the agenda of a democratically elected president.
The White House’s appetite for a fight with the legal industry appears to have waned. There hasn’t been a new executive order since early April.
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