For the legal industry—and Big Law in particular—the second Trump administration is off to a turbulent start.
President Trump has issued executive orders blacklisting several large law firms that have represented clients opposed by the administration.
The orders essentially cut off firms’ access to the federal government, suspending their lawyers’ security clearances, blocking access to government buildings, preventing government hiring of firm employees, and requiring federal agencies to terminate contracts with the firms.
Trump has also targeted diversity, equity and inclusion (DEI) programs and launched a regulatory probe into hiring practices at several major firms.
Since March, he has extracted promises from several Big Law players that they will rethink their DEI initiatives, hire lawyers from across the political spectrum, and offer financial concessions to fund pro-administration legal causes. In exchange, those firms have been spared punitive executive orders.
While some firms are bowing to the pressure, a few major players are fighting back in court, arguing Trump has overstepped his executive authority and violated their First Amendment rights.
All of this comes at a critical moment for law firms and their clients. Both face financial headwinds and deep uncertainty stemming from Trump’s tariff war.
How law firms navigate this volatile political and economic environment could redefine their businesses, client relationships, and reputations.
Changing Course on DEI
On March 6, Trump signed an executive order directing the Equal Employment Opportunity Commission and the U.S. attorney general to review the DEI practices of “large, influential, or industry-leading law firms.”
The order said the EEOC should review whether firms “reserve certain positions, such as summer associate spots, for individuals of preferred races; promote individuals on a discriminatory basis; permit client access on a discriminatory basis; or provide access to events, trainings, or travel on a discriminatory basis.” As he signed the order, Trump said the administration was specifically looking at “15 different firms,” though he did not disclose the firms’ names.
Two weeks later, the EEOC’s acting chair followed up, sending letters to 20 law firms—all from the upper tiers of the Am Law 100—requesting information about their DEI-related employment practices. “The EEOC is prepared to root out discrimination anywhere it may rear its head, including in our nation’s elite law firms,” Andrea Lucas, the acting chair, said in a press release. “No one is above the law—and certainly not the private bar.”
The administration’s moves have chilled DEI efforts at many firms. At least 40 major firms have altered their policies or removed pro-DEI statements from their websites, a trend that began after Trump’s inauguration and has accelerated since the executive order.
Eight large firms have also reached deals with Trump that they will not engage in “illegal DEI discrimination and preferences.”
On April 8, Bloomberg News reported that one of the firms, Skadden Arps Slate Meagher & Flom, had canceled all future events for the firm’s employee affinity groups and had removed mentions of those groups from its website. Skadden, Bloomberg said, supported at least 10 affinity networks “for parents, veterans, Asian-Pacific Islanders, Blacks, and Latinos, among others.”
Preemptive Agreements
Skadden, in its deal with Trump, also said it would spend $100 million on pro bono causes that the administration supports.
Willkie Farr & Gallagher, Cadwalader Wickersham & Taft, and Milbank have also committed $100 million, Paul, Weiss, Rifkind, Wharton & Garrison has pledged $40 million, and Kirkland & Ellis, Allen Avery Shearman & Sterling, Latham & Watkins, and Simpson Thacher & Bartlett promised $125 million.
On Truth Social, Trump said the agreements will “help end the weaponization of the justice system and the legal profession.” For their part, the firms have acknowledged in internal communications that the agreements are a preemptive move to prevent Trump from targeting them with business-crushing executive orders.
The deal terms are broad. The firms have committed to pro bono efforts helping veterans and public servants (including military, law enforcement and first responders), fighting antisemitism, and ensuring fairness in the justice system. They have also agreed to commit to “merit-based hiring, promotion, and retention,” and to give “fair and equal consideration” to job candidates regardless of political ideology. As Milbank noted in its statement about the deal, “the agreement is consistent with [the firm’s] core values.”
The deal terms are broad. Skadden, Milbank, Willkie, and Paul, Weiss have committed to pro bono efforts helping veterans and public servants (including military, law enforcement and first responders), fighting antisemitism, and ensuring fairness in the justice system.
They have also agreed to commit to “merit-based hiring, promotion, and retention,” and to give “fair and equal consideration” to job candidates regardless of political ideology.
As Milbank noted in its statement about the deal, “the agreement is consistent with [the firm’s] core values.”
While the relatively loose language may give firm leaders some comfort, the terms may also allow Trump opportunities to pressure them to represent certain clients. In recent days, for instance, he has said he may also lean on the firms to assist the coal industry with leasing on public lands.
Internal and External Criticism
Many of the firms have received substantial pushback from critics inside and outside the firms. At Willkie, for instance, The New York Times reported that Doug Emhoff, a prominent partner at the firm and husband of Trump’s 2024 opponent, former Vice President Kamala Harris, has “publicly assailed” the deal, and Joseph Biao, Willkie’s longest-serving lawyer, resigned in protest.
Democrats have also questioned the deals.
The ranking members of the House and Senate judiciary committees—U.S. Sen. Richard Blumenthal (D-Conn.) and Rep. Jamie Raskin (D-Md.)—sent a letter to the four firms that have inked deals with Trump seeking information and records. They also wrote to Kirkland & Ellis and Sullivan & Cromwell for material about their role in “facilitating the administration’s unlawful coercion of other law firms."
Blumenthal and Raskin noted that the federal courts have so far sided with law firms over the administration.
“The courts that have considered these vendetta orders to date have universally ruled against them and noted that they violate the First Amendment right to free speech as they are plainly ‘retaliatory action’ meant to ‘chill speech and legal advocacy,’” Blumenthal and Raskin wrote.
President Trump announced agreements on Friday with Kirkland & Ellis LLP and four other prominent law firms to collectively provide hundreds of millions of dollars in pro bono legal services for causes supported by his administration, Associated Press reported.
These agreements also allow the firms to avoid potential executive orders that could have posed challenges to their operations.
The resolutions highlight the administration’s ability to negotiate with major law firms to achieve its goals. These firms, which include Kirkland & Ellis LLP, Allen & Overy LLP, Shearman & Sterling LLP, Simpson Thacher & Bartlett LLP, and Latham & Watkins LLP, have agreed to contribute $125 million each in free legal services. These efforts will support initiatives such as veterans’ affairs and combating anti-Semitism.
In exchange, the administration has withdrawn letters from the EEOC requesting information about potential discriminatory hiring practices at these firms. This resolution reflects a balancing act between the firms’ cooperation with government priorities and their interest in mitigating possible regulatory scrutiny.
The agreements demonstrate the evolving relationship between the legal sector and government policy, providing insight into how law firms navigate compliance while contributing to public causes.
Fighting Back in Court
Perkins Coie, WilmerHale, and Jenner & Block have sued the Department of Justice over Trump’s executive orders targeting the firms.
On March 12, a federal judge issued a preliminary injunction blocking the administration from enforcing portions of the order against Perkins. Judges, in two separate rulings on March 28, followed suit, freezing Trump’s orders against WilmerHale and Jenner & Block.
The three firms are now seeking permanent injunctions against the administration.
They argue that Trump has trampled on their First Amendment rights and is retaliating against them because they have represented clients opposed to the administration and its allies. “These orders send a clear message to the legal profession: Cease certain representations adverse to the government and renounce the administration’s critics—or suffer the consequences,” Jenner said in court documents.
The firms have also mounted a campaign to generate support for their arguments. Hundreds of law firms, law professors, former judges, and advocacy groups have filed amicus briefs in the Perkins case. And Jenner has created a standalone website, “Jenner Stands Firm,” which tracks developments in its case.
As the court fights continue, however, Trump’s orders are inflicting pain.
An Associated Press account of a hearing on Perkins Coie’s injunction highlighted the financial impact the executive order is having on the firm. The firm’s attorney, Dane Butswinkas of Williams & Connolly, said all 15 of Perkins’ top clients have government contracts and that several clients had parted ways with the firm or were considering doing so, the AP reported.
Continuing the order, Butswinkas said, would “spell the end of the law firm.”
Tariffs: Turmoil and Opportunity
Being shut out of the federal government—particularly at the beginning of a new administration when clients are attempting to understand and react to seismic policy changes—is hardly an optimum position for any major firm.
And that’s especially true at the moment, as Trump reels off new tariff policies on a daily basis.
As Bloomberg recently reported, international trade practices are grappling with “a frenzy” of work. “While few would argue Trump has been good for the legal profession writ large — see his revoking of security clearance to pressure firms on his enemies list—trade lawyers have to admit he’s been good for their niche corner of the industry,” Bloomberg said.
In the wake of Trump’s tariffs, companies are scrambling to review and rewrite contracts with suppliers, understand whether free trade agreements may exempt their products, identify and manage risks to their supply chains, and pinpoint and cope with increased costs. Contract renegotiations and fights over who bears the costs of new trade barriers are also likely to trigger a wave of litigation. All of this could mean a windfall for well-positioned firms.
Trump, too, sees a role in the tariffs war for firms that have struck deals with him. "Right now, Japan is flying here to make a deal. South Korea is flying here to make a deal. And others are flying here," Trump said on April 8. "We're going to have to use those great law firms, I think, to help us with that."
Tough Choices
Meanwhile, the administration’s moves against law firms continue.
On April 9, Sussman Godfrey—which won a $787.5 million settlement from Fox News on behalf of Dominion Voting Systems over lies about the 2020 election—was hit with an executive order similar to those against WilmerHale, Perkins, and Jenner. Sussman said it intends to fight the order.
Almost certainly, other firms will face the same choice—whether to accommodate the administration or confront it. Neither option is easy.
On one hand, firms face a real threat to their finances and clients. On the other, a firm’s reputation may be permanently damaged. For firms that have accepted deals, recruiting efforts are already in turmoil, and they are taking critical lumps from their colleagues and peers. It’s not clear how firms caught in Trump’s net can avoid the proverbial rock or the hard place.
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David L. Brown is a legal affairs writer and consultant, who has served as head of editorial at ALM Media, editor-in-chief of The National Law Journal and Legal Times, and executive editor of The American Lawyer. He consults on thought leadership strategy and creates in-depth content for legal industry clients and works closely with Best Law Firms, as senior content consultant.
