Big Law’s Trump Deals Pose Ongoing Risks, Keker Leaders Warn

Sept. 8, 2025, 9:30 AM UTC

President Trump’s deals with Big Law firms pose ongoing risks to the profession, said leaders of a law firm that was among the first to criticize the pacts.

There’s risk the White House will call on dealmaking firms to justify rolling federal troops into US cities or some other legally suspect tactic, said Steven Ragland, associate general counsel at Keker, Van Nest & Peters. The administration also may again use threats to bend law firms to its will, he said.

“When the bully says, ‘OK now it’s time to give me your lunch money again,’ what’s going to happen?” Ragland said in an interview. “We will see what will be done and what sort of damage might be done.”

Steven Ragland
Steven Ragland
Keker, Van Nest & Peters

Keker, Van Nest & Peters, a single-office group of boutique litigators in San Francisco known for representing tech clients, was one of the most outspoken partnerships pushing back against Trump’s orders and criticizing firms for signing the deals.

Bloomberg Law’s wide-ranging interview Sept. 4 with Ragland and Laurie Mims, the firm’s managing partner, show that some legal leaders remain as concerned about the Trump deals as when they first spoke out against them more than five months ago.

In addition to the deals, Mims said she is concerned about Trump’s personal attacks against judges who have ruled against him. District court judges she knows have received “terrifying” hate mail and threats, she said, without identifying those judges.

Trump in March personally attacked US District Judge James Boasberg, calling for his impeachment and labeling him a “radical left lunatic” on social media after the jurist ruled against a Trump administration anti-immigration campaign it tried to justify under the Alien Enemies Act of 1798. That led to a rare public statement from Chief Justice John Roberts rebuking calls to impeach judges for disagreeing with their rulings.

“Many jurists, at significant personal risk, are willing to follow the rule of law,” Mims said. “That is heartening. And it remains to be seen whether the Supreme Court will do what it should do in these cases.”

The Deals

Nine Big Law firms in March and April pledged $940 million in free legal services to Trump to avoid punitive executive orders. While it’s unclear what if anything the firms have since done to honor their commitments, at least one of them, Kirkland & Ellis, has worked on trade deals for the government, lobbyist Brian Ballard confirmed during a Bloomberg Government roundtable on Sept. 3.

In the weeks after Trump’s attacks, Keker, Van Nest signed an amicus brief backing Perkins Coie’s fight against an order, senior partners penned an essay in the New York Times titled, “Our Law Firm Won’t Cave to Trump. Who Will Join Us?,” and firm co-founder John Keker appeared in a “60 Minutes” segment where he called firms’ deals with Trump “bribery.”

There’s a risk firms that cut deals with the administration could be perceived as having a conflict of interest fighting for clients against the government, Ragland said. “If I’ve basically signed on to not challenge the administration in certain ways, or that’s the implication, I don’t know whether it actually creates a conflict, but I think it is a concern,” he said.

Laurie Mims
Laurie Mims
Keker, Van Nest & Peters

Mims said the firm’s nearly 50 partners unanimously supported the decision to speak out. Clients “pretty universally” responded well to the firm’s stand, and some new business came to the firm because of its stance, she said.

“There are still risks of losing clients or the government taking action against our firm or others,” Mims said. “We’re aware the risks are there. But it was the thing we all felt we had to do. It was just such a clear violation of what we understand to be our constitutional system.”

New Recruits

Lawyers have sought to join the firm after its opposition to the Trump administration, Ragland said.

“Our associates were united in thanking us for doing it and telling their friends, ‘My firm did this, how about yours?’” Ragland said. “It’s only helped with our recruitment.”

Keker in July hired associate JiLon Li from Paul, Weiss, Rifkind, Wharton & Garrison, one of the dealmaking firms, which has seen departures from its litigation group in the aftermath of its agreement, Mims said. “These firms have suffered a significant reputational hit with law students,” she added.

In addition to speaking out, the firm has taken on clients adversarial to Trump.

Keker, Van Nest challenged Trump in his first term over an executive order denying federal funds to state or local governments with so-called “sanctuary city” policies. The firm won a permanent injunction that was upheld on appeal.

Firm lawyers in February brought a lawsuit on behalf of United Farm Workers over a Department of Homeland Security immigration raid in Kern County, California. It also challenged the administration’s “deferred resignation” program, representing a union of government employees arguing executive orders targeting their employment are unlawful.

Tech Clients

Keker and Yale Law School classmate Bill Brockett founded the firm in 1978, and it has gone on to develop a top-tier reputation as a litigator for companies such as Alphabet Inc.’s Google, Qualcomm Inc., and Electronic Arts Inc.

The firm has been defending OpenAI in copyright infringement lawsuits brought by media companies. In many of the cases it’s going up against another high-powered trial firm, Susman Godfrey. The cases are bogged down in discovery fights, Mims said, indicating there’s no resolution in sight.

“There is basically a discovery scuffle every week, but they are important fights as to the extent of discovery that will be allowed in those cases,” she said.

The OpenAI cases came through a relationship the firm developed with a former Google in-house lawyer, Renny Hwang, who is now at OpenAI. Hwang was a main client contact in the firm’s representation of Google in a landmark patent and copyright trial against Oracle Corp. The firm won for Google in a decade-long case that resulted in a US Supreme Court ruling.

To contact the reporter on this story: Roy Strom in Chicago at rstrom@bloombergindustry.com

To contact the editors responsible for this story: John Hughes at jhughes@bloombergindustry.com; Alessandra Rafferty at arafferty@bloombergindustry.com

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