In Trump’s $940 Million Deals With Firms, the Jury Is Still Out

Nearly five months after major law firms began striking deals with President Donald Trump, there’s little outward sign that the agreements have impacted their business operations.

Some of the nine firms that pledged a collective $940 million in free legal services as part of the pacts have continued to take the kinds of cases that appear to have made them targets in the first place. At least one is fighting the Trump administration in court over immigration and trade issues central to the president’s agenda.

The vague terms of the deals made them attractive to firms seeking to avoid war with the White House and hoping Trump would quickly move on. Still, the looseness around the agreements also creates risk for firms trying to navigate an administration that thrives on unpredictability.

“Trump’s own conception of them is subject to repeated change, so it’s hard to analyze them as if they were regular contract or client arrangements,” said Walter Olson, a senior fellow at the Cato Institute.

There are signs that Trump allies are angling to put the firms to work with assignments that may never become public. Kirkland & Ellis, the world’s largest law firm by revenue, worked on new US trade deals with Japan and Korea after being connected with administration officials by Boris Epshteyn, Trump’s personal lawyer, The New York Times reported this week. The president said in the wake of the deals that he would look to enlist the firms on tariff issues, as well as efforts to boost coal mining and defend law enforcement officers accused of civil rights violations.

Four major firms that opted to challenge Trump in court after being hit with punitive executive orders say the president’s efforts to intimidate lawyers are attacks on the rule of law. All four won rulings striking down the orders—which threatened to bar access to federal buildings and kill clients’ government contracts—as unconstitutional.

Proud Boys, Sanctuary Cities

The most noticeable impact of the deals may be on the firms’ websites, where they have largely scrubbed references to diversity and inclusion initiatives they once trumpeted. The firms have also seen some lawyers hit the exits in the wake of the agreements, most notably a group of high-profile litigators who left Paul Weiss to launch their own firm.

Harder to track is how the deals have impacted firms’ decisions on what cases to take, whether it’s pro bono matters that clash with Trump’s agenda or lining up directly against the administration in court. Mayer Brown, a large firm that stayed off Trump’s target list and did not make a White House deal, has been “being very careful about picking our spots” when to comes to issues that are “personal to the president,” Jon Van Gorp, the firm’s leader said in a July interview.

Lawyers from New York-founded Milbank LLP have continued to represent clients opposing Trump directly in litigation on hot button issues after cutting a deal. Neal Katyal, a former acting solicitor general in the Obama administration, is part of a team challenging the president’s authority to impose steep tariffs on imports from other countries. Katyal and Milbank partner Gurbir Grewal also are defending New Jersey cities against a Justice Department lawsuit over immigration-related policies, agreeing to slash their hourly rates for the work.

Katyal and a Milbank spokesperson didn’t respond to comment requests.

Paul Weiss was the first firm to make a deal with Trump, days after the president hit it with an executive order. The president in the March 14 order slammed the firm for its ties to attorneys who worked on special counsel Robert Mueller’s investigation of alleged Russian interference in the 2016 presidential election and the Manhattan district attorney’s investigation into Trump’s finances. He also singled out the firm for pro bono work on a lawsuit against right-wing groups Proud Boys and Oath Keepers, which were accused of vandalizing a church amid the Jan. 6, 2021 riot at the US Capitol.

Paul Weiss has continued to fight the groups, however, filing an Aug. 4 lawsuit in New York accusing Proud Boys and its leader of infringing trademarks awarded to the Metropolitan African Methodist Episcopal Church after the attack on the church. A firm spokesperson did not respond to a request for comment.

Business Decisions

A Kirkland & Ellis spokesperson declined to comment on the report of its trade work for the Trump administration. A spokesperson for Skadden, which the report said was contacted for similar work, did not respond to a request for comment.

Advising on the new trade deals is an attractive way for firms to pay off their free legal services tab, said legal ethics professors Rebecca Roiphe and Stephen Gillers.

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The work could offer “extraordinarily valuable” experience to lawyers at the firms, which are some of the country’s most profitable and advise corporate clients around the world.

“These are businesses, and what they’re really attentive to is not doing anything that will explode their business model and force clients to flee,” said Rebecca Roiphe, an ethics professor at New York Law School.

Still, it’s not clear if firms are feeling any heat to make good on the White House promises.

The deals do not impose deadlines on the free legal services or specify how they will be enforced. At least some of the agreements were never signed.

The court rulings against the executive orders targeting other firms have also likely tamped down any sense of urgency. The Justice Department is appealing the decisions, but the president has said little publicly about the orders and the deals with the firms in the months since the last agreements were announced.

(An incorrect AI summary previously at the top of this story was removed.)