'Beyond wildest dreams': Experts claim Trump can't believe law firm ploy worked
U.S. President Donald Trump sits in the Oval Office at the White House, in Washington, D.C., U.S., June 10, 2025. REUTERS/Nathan Howard

President Donald Trump's executive orders targeting law firms are being shot down in court, and his administration's refusal to challenge those losses should encourage firms to renounce their surrenders, according to a report.

The administration typically files quick appeals to its court losses, but Trump lawyers have not done anything to challenge rulings that rejected his attempts to punish prominent law firms that represent clients or causes he doesn't like – which experts say gives away the game, reported the New York Times.

“They knew that these were losing positions from the beginning and were not actually hoping to win in court, but rather to intimidate firms into settling, as many firms did,” said W. Bradley Wendel, a law professor at Cornell who is an authority on legal ethics. “Now that they have racked up the four losses in district courts, it is not surprising that they are not appealing, because I don’t think they ever thought these were serious positions.”

Three rulings permanently blocked executive orders targeting the law firms Perkins Coie, Jenner & Block and WilmerHale, and a judge temporarily blocked another order against Susman Godfrey. But some firms – Paul Weiss, Skadden and Latham & Watkins – chose to surrender to the president and agreed to provide hundreds of millions of dollars in free legal work.

“The Trump administration probably feels like it has already succeeded beyond its wildest dreams,” said Yale Law School professor Harold Koh. “It never expected such capitulation. Through blatantly unconstitutional actions, it extracted deals from nine leading law firms for approaching $1 billion in coerced pro bono legal services and has chilled litigation and public opposition from law firms nationwide.”

The precise terms of the deals remain somewhat mysterious, even to the courts.

"Are the precise terms of the deals cut with the law firms and President Trump written down or memorialized in some way?” asked federal judge Beryl Howell at an April 23 hearing, and government lawyer Richard Lawson admitted that he didn't know much more than “what I have read in the papers.”

Another judge, Loren AliKhan, asked a similar question two weeks later in another case, and Lawson again said he didn't know anything more than "the generally publicly available information."

Judges have repeatedly ruled that Trump's orders were clearly unconstitutional, but its strategy has succeeded in pushing law firms the president doesn't like.

“Its legal arguments have been resoundingly rejected by all lower courts who have ruled, so why appeal and have that illegality confirmed?” Koh said. “It could only weaken the administration’s posture.”

Koh added that the administration's decision not to challenge those losses should encourage the firms that surrendered to awal away from the murky deals they made.

“All the more reason why the nine firms who ‘settled’ should now renounce the coerced deals and make clear that they still control their own pro bono case selection," Koh said.