How Trump Is Putting Law Firms in a No-Win Situation

New York Times

09-04-2025

Willkie Farr & Gallagher last week became the latest law firm to strike a deal with the White House and escape President Trump's wrath. But the firm, which pledged $100 million in legal services to causes that the Trump administration supports, traded one problem for another.
Willkie has faced a backlash to the deal in recent days, including within its ranks, as concerns mount over Mr. Trump's broader law firm crackdown.
Doug Emhoff, former Vice President Kamala Harris's husband and one of Willkie's most prominent partners, publicly assailed the agreement with Mr. Trump. Congressional Democrats are now demanding information about the deal. And Willkie's longest-serving lawyer, Joseph T. Baio, resigned rather than stay at a firm that gave in to the White House's demands.
In an email to the firm's executive committee, Mr. Baio wrote that he had left so he could 'join the fight against governmental tyranny, unconstitutional decrees and social injustice, particularly at this critical time.'
The fallout at Willkie, which counted Mr. Trump among its clients decades ago, illustrates the no-win predicament facing law firms caught in Mr. Trump's cross hairs. If they resist, the firms jeopardize their bottom line, exposing themselves to executive orders that, while legally dubious, imperil their businesses. But if they buckle, they are seen by critics as having compromised their integrity, drawing rebukes from across the broader legal community.
'We know this news is not welcomed by some of you, and you would have urged a different course of action,' Willkie's executive committee said in an email to the firm last week explaining the deal. 'Needless to say, this was an incredibly difficult decision for firm leadership.'
The negotiations that led to the deal, recounted in interviews with people briefed on the matter, demonstrate Mr. Trump's new strategy for bringing law firms to heel. Mr. Trump's advisers have begun contacting firms before the president issues an executive order — sometimes through a friendly intermediary — to suggest that they sign a deal, or else.
Willkie learned in late March that it was potentially next on Mr. Trump's list. The firm's chairman, Thomas M. Cerabino, spoke with Thomas J. Barrack Jr., a Willkie client and longtime friend of Mr. Trump's. Mr. Cerabino then spoke with Boris Epshteyn, Mr. Trump's outside legal adviser, who indicated that it would be best for both sides if a deal was reached, according to people briefed on the matter.
Other firms, including Cadwalader, Wickersham & Taft, were recently contacted under similar circumstances. Cadwalader has yet to reach a deal, but several other firms have done so.
Soon after Willkie reached a deal, the law firm Milbank did the same, saying later that 'the Trump administration suggested to us that we enter into an agreement similar to one recently agreed to by Skadden,' another large firm that proactively struck a deal.
The alternative, those firms concluded, was worse. Over the last month, Mr. Trump targeted several other firms with executive orders that jeopardized their ability to represent government contractors, and limited their access to federal buildings. Those firms, including Perkins Coie and Jenner & Block, are fighting the orders in federal court, where judges have already blocked most of the restrictions.
Perkins Coie has disclosed that Mr. Trump's order has taken a financial toll on the firm. And although Willkie's agreement required it make certain concessions, the firm's executive committee said in its statement to employees that an executive order would have imperiled 'our clients' rights and those of our firm.'
Karoline Leavitt, the White House press secretary, said in a statement that 'Big Law continues to bend the knee to President Trump because they know they were wrong, and he looks forward to putting their pro bono legal concessions toward implementing his America First agenda.'
Mr. Cerabino, the Willkie chairman, did not respond to requests for comment.
Mr. Baio, 71, a former Willkie partner and member of the firm's executive committee, said in an interview that he understood the difficult situation.
But Mr. Baio, who had been working full time as a senior counsel in Willkie's litigation department, decided he could no longer stay after the deal. So he resigned, leaving the firm after 47 years.
Andrew Silberstein, an associate at Willkie, also resigned in protest, lamenting in an email to colleagues that the firm's principles had been 'so deeply compromised,' and that 'they have come for us, and we did not speak out.' Associates at other firms targeted by Mr. Trump have also resigned.
Mr. Emhoff has remained at Willkie. But at a charity event last week, he denounced the firm's decision to capitulate to Mr. Trump, according to a person with knowledge of the matter.
'I wanted them to fight a patently unconstitutional potential executive order,' he said at the event. Mr. Emhoff's criticism was reported earlier by CNN.
Democratic lawmakers have also expressed concern about the deal. In a letter to Willkie this week, the top Democrats on the Senate Permanent Subcommittee on Investigations and the House Judiciary Committee questioned how the deal came about and raised what they called 'the troubling prospect that the president has successfully and unlawfully coerced' the firm.
'The American people and Congress deserve transparency with respect to the president's ongoing assault on constitutional rights and the rule of law,' Senator Richard Blumenthal of Connecticut and Representative Jamie Raskin of Maryland wrote in the letter.
Mr. Blumenthal and Mr. Raskin also sent letters to Skadden and other firms.
While the list of firms on Mr. Trump's radar appears arbitrary at times, Willkie was an obvious target, and not only because of Mr. Emhoff.
The president's advisers were most focused on the firm employing a former top investigator for the congressional committee that scrutinized Mr. Trump's role in the Jan. 6, 2021, attack on the Capitol, according to a person close to Mr. Trump. They also focused on the fact that the firm's clients included two Georgia election workers who had sued Rudolph W. Giuliani, Mr. Trump's former personal lawyer.
Mr. Trump was also once a client. In the late 1980s, when the firm was much smaller, Willkie worked on cases on Mr. Trump's behalf as he built himself into a local player with three casinos in Atlantic City.
One of the people who worked closely with Mr. Trump's company at the time was Mr. Cerabino, now the firm's chairman.
Decades later, Mr. Cerabino was at the center of the discussions with Mr. Trump's White House.
In its internal statement, Willkie's executive committee made oblique references to the discussions with Mr. Barrack and Mr. Epshteyn, without mentioning them by name. The firm, the statement said, was 'invited to contact the administration,' which then 'outlined a proposed alternative to receiving an executive order.'
Mr. Barrack, who was nominated as ambassador to Turkey, was represented by Willkie in a criminal trial in 2022, when he was acquitted on charges that he secretly worked as a foreign agent. Mr. Barrack's private equity real estate firm is also a major Willkie client.
When Mr. Barrack spoke to Mr. Cerabino in late March, he said that the firm may want to get in touch with Mr. Trump's team, and quickly. The firm's leadership took two paths. At the same time that it prepared to go to court to fight any potential order, it began discussions with Mr. Trump's team, according to a person briefed on the matter.
After Mr. Cerabino spoke with Mr. Epshteyn, the firm's leadership conferred in two executive committee meetings, deciding that striking a deal was the most prudent decision. It was announced soon after.