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Some law firms that cut deals with Trump take cases opposing his administration
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Some law firms that cut deals with Trump take cases opposing his administration
Sep 16, 2025 3:22 AM

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Law firms represent clients against Trump despite deals

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Cases involve transgender rights and "sanctuary cities"

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Other cases involve immigration and an offshore wind farm

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Firms pledged to do pro bono work for Trump causes

By David Thomas and Mike Scarcella

Sept 16 (Reuters) - 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.

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