Law Firms Who Cut Deals Take Cases Against Trump Policies
By Reuters | 16 Sep, 2025

Of the nine mega-firms Trump bullied into agreeing to provide free legal services for the government, four have continued taking cases that oppose his policies.

When nine U.S. law firms struck agreements with President Donald Trump in March and April to head off a crackdown on their business, it prompted broad concern that the deals would deter them from taking cases against his policies. Months later, at least four of them are involved in lawsuits opposing Trump's administration in cases involving transgender rights, immigration, tariffs and wind power, court records show.

The four firms are Latham & Watkins; Willkie Farr & Gallagher; Skadden, Arps, Slate, Meagher & Flom; and Milbank. They represent clients that have sued the administration since May, after the agreements were reached. 

It is unclear whether these four firms or others may still be steering clear of certain cases for fear of drawing Trump's ire or imperiling their agreements with the Republican president. Some legal experts said law firms may be wrestling with competing pressures, since representing clients against the government is a key driver of business and prestige. 

"A lot of litigation is opposed to the federal government," said Michael McCabe, a business lawyer who advises other attorneys on ethics matters. "All of that work is an important part of a law firm economy."

A joint venture backed by Orsted retained Latham & Watkins to sue the administration this month after the federal government halted construction on the Danish energy company's Rhode Island offshore wind farm. 

Willkie Farr is representing school districts in Virginia's Arlington and Fairfax counties that sued the administration last month. They are seeking to protect federal funding threatened by Trump's Department of Education, which decided that their policies of letting transgender students use bathrooms and locker rooms that align with their gender identity violated federal education law that bars sex discrimination. 

Milbank in June began representing small businesses that sued to challenge Trump's use of emergency powers to impose sweeping tariffs. The firm in July also began representing the New Jersey cities of Newark and Hoboken, which were accused by the administration of unlawfully shielding residents from federal immigration enforcement.

Skadden partnered in May with the National Immigrant Justice Center, a nonprofit that advocates for low-income immigrants, to sue the administration on behalf of a Mexican woman who was denied a visa designed for crime victims.

The firms and the White House did not immediately respond to requests for comment.

'WEAPONIZING' THE LEGAL SYSTEM

Trump, who returned to office in January, issued executive orders against five firms that he accused of "weaponizing" the legal system against him and his allies and promoting workplace diversity policies he called discriminatory. The directives sought to strip the firms of security clearances and restrict their access to federal officials, buildings and contracting work.

The targeted firms had represented Trump's political adversaries or clients bringing legal challenges to his policies, or had employed attorneys who took part in past government investigations aimed at the president.

Four of the targeted firms sued Trump to challenge the executive orders. A fifth, Paul Weiss, reached an agreement with Trump, and the president rescinded the directive against the firm. All told, nine firms entered into such agreements, pledging to donate a total of nearly $1 billion in free legal work to causes favored by the administration.

The agreements, touted by Trump on social media, did not appear to bar the firms from representing clients in cases against the administration, but critics warned they could have a chilling effect.

The firms "decided to permit President Trump to suppress their speech and dictate who they can and cannot take as clients," U.S. Senator Richard Blumenthal and U.S. Representative Jamie Raskin, both Democrats, wrote in an April 18 letter to five of the firms that made such agreements.

In internal emails and written responses to the lawmakers, leaders of firms have defended their deals and said they retain control over the legal matters they handle.

The four firms that sued Trump won rulings declaring the orders a violation of the U.S. Constitution's First Amendment protections against government abridgment of freedom of speech. The administration has appealed those decisions.

A Reuters investigation in July found that dozens of major law firms, wary of retaliation, have broadly scaled back pro bono work, workplace diversity initiatives and litigation that could place them in conflict with Trump. Reuters also found that top firms had pulled back from litigation against the U.S. government. 

IMPORTANT CLIENTS

Legal industry experts said the lawsuits involving the four firms that have reached agreements with Trump include the kinds of matters large firms cannot easily give up, serving important clients or spearheaded by key lawyers at the firms.

For example, Orsted has relied on Latham for years, turning to the firm in a $680 million financing deal with JPMorgan last year and in prior litigation related to a New Jersey offshore wind project during Democrat Joe Biden's presidency.

Orsted's joint venture Revolution Wind said in its new lawsuit that it already had spent about $5 billion on the Rhode Island project halted by the administration and could lose another $1 billion if it is not restarted. The lawsuit accuses the administration of violating its due process rights under the Constitution and violating federal laws and regulations.

The company did not respond to a request for comment on its work with Latham.

Arlington and Fairfax counties, located in the Washington suburbs, are being represented by a leader of Willkie's government investigations practice, Timothy Heaphy. He previously served as U.S. attorney for the Western District of Virginia, appointed to that post by Democratic former President Barack Obama. 

The Arlington and Fairfax school boards are appealing a federal judge's dismissal of their lawsuits. They did not respond to questions about their relationship with Willkie.

Milbank partner Neal Katyal, who often argues cases before the U.S. Supreme Court and is a Trump critic, has had a lead role in the tariff litigation brought by small businesses since June. 

Katyal and Milbank's Gurbir Grewal, a former New Jersey attorney general who was the U.S. Securities and Exchange Commission's enforcement director under Biden, are defending Newark and Hoboken against Trump's "sanctuary cities" crackdown.

Milbank has the experience in arguing cases before the Supreme Court needed in the tariff case, according to Sara Albrecht, board chair of the Liberty Justice Center, which is serving as co-counsel. Lower courts sided with the plaintiffs, and the Supreme Court is due in November to hear arguments in the Justice Department's appeal. 

Officials for Newark and Hoboken did not respond to requests for comment. 

Skadden and the National Immigrant Justice Center had worked together on asylum cases before Trump's second term as president. Neither responded to requests for comment.

(Reporting by David Thomas in Chicago and Mike Scarcella in Washington; Editing by David Bario, Amy Stevens and Will Dunham)