The elite law firm Skadden, Arps, Slate, Meagher & Flom has had discussions with President Trump’s advisers about a deal to avert the type of executive order that the White House has been imposing on many of its competitors, according to five people briefed on the matter who were not authorized to speak publicly about private conversations.
The talks represent an extraordinary turn in Mr. Trump’s campaign against law firms and the legal system more broadly, marking what appears to be the first time that a major firm has tried to cut a deal with the president before he could issue an executive order. Recent orders targeting other law firms have restricted the work they can do with the federal government.
The Skadden discussions are also the latest example of how large law firms, afraid of a protracted battle with Mr. Trump, are eager to strike deals.
The White House has signaled that more firms are in the president’s sights to receive executive orders, particularly those that employ lawyers who have worked on investigations into Mr. Trump or on causes that his supporters object to.
On Thursday night, Mr. Trump took aim at an additional law firm, issuing an executive order suspending the security clearance for WilmerHale, a large firm that was once home to Robert Mueller III, the former F.B.I. director who served as special counsel on the investigation into alleged Russian interference in the 2016 presidential election on behalf of Mr. Trump.
Mr. Mueller returned to WilmerHale after his investigation and formally left the Washington-based law firm in 2021.
The executive order blasted the firm for hiring lawyers who “weaponize” the legal system, engage in “partisan representations” and abuse its practice of providing free legal services to organizations.
In a statement, WilmerHale said, “We look forward to pursuing all appropriate remedies to this unlawful order.”
While WilmerHale vowed to fight the order, Skadden was not the only firm in discussions with Mr. Trump’s team, according to two people briefed on the matter, and multiple deals could be announced in the coming days.
It is unclear how the talks got started or whether Skadden will reach an agreement with Mr. Trump. But on Wednesday, the president hinted that such deals might emerge and boasted about his track record of bringing big law firms to heel.
“They’re all bending and saying, ‘Sir, thank you very much,’” Mr. Trump said, adding that law firms are saying, “‘Where do I sign? Where do I sign?’”
A spokeswoman for Skadden did not respond to several requests for comment. A White House spokesman declined to comment.
Although it is unclear precisely why Skadden drew the White House’s attention, there were recent signs that the firm could be next. In a post on his social media platform, X, on Sunday, Elon Musk singled out Skadden’s work assisting in a lawsuit against Dinesh D’Souza, the right-wing media critic and political commentator.
“Skadden, this needs to stop,” Mr. Musk wrote in his post, referring to the firm’s work on behalf of a private citizen who said Mr. D’Souza had falsely accused him of ballot fraud in a documentary about the 2020 election.
The post was somewhat surprising because lawyers from Skadden represented Mr. Musk during his acquisition of Twitter in 2022.
The discussions between Skadden and the Trump advisers come one week after another prominent law firm, Paul Weiss, cut a deal with Mr. Trump that was widely criticized in the legal community as a capitulation to a brazen and possibly unconstitutional executive order.
Mr. Trump’s order against Paul Weiss, which has extensive ties to Democrats and anti-Trump causes, had gone so far as to restrict the firm’s lawyers from entering government buildings.
Mr. Trump agreed to drop the order in exchange for Paul Weiss’s commitment to represent clients no matter their political leanings and a donation of $40 million in free legal service to causes Mr. Trump has championed.
The leaders of Paul Weiss said that Mr. Trump’s order would have decimated their business — and that rivals were looking to poach some of their top lawyers. But the firm’s agreement appears to have emboldened the president and encouraged other firms to consider making their own deals.
The flurry of actions taken by Mr. Trump against law firms has, for the most part, been met with silence from industry leaders. Lawyers have been reluctant to speak out for fear of making their firm a target.
In this void, law school deans and bar associations have issued statements denouncing the actions taken by the president and warning that punishing law firms because of whom they represent is a serious threat to the rule of law.
On Tuesday, Jenner & Block became the latest big law firm to receive an executive order. The order, like the ones against Jenner’s competitors, accused the law firm of engaging in “lawfare.” The order also singled out Jenner’s pro bono practice, claiming that the law firm had used it “to engage in activities that undermine justice and the interests of the United States.”
One of Jenner’s former partners, Andrew Weissmann, had worked closely with Mr. Mueller in his investigation of the ties between Mr. Trump’s campaign and Russia during his first term.
Skadden also found itself swept up in Mr. Mueller’s investigation into Russian potential interference in the 2016 election, though the issues had little connection to Mr. Trump. Mr. Mueller’s inquiry had focused on some of the lobbying work Skadden lawyers had done for Ukraine’s former pro-Russian government.
So far, Perkins Coie is the lone law firm willing to go to court to fight Mr. Trump over one of his executive orders — and it is having some initial success.
In an order temporarily barring a major portion of Mr. Trump’s order from taking effect, a federal judge in Washington suggested that it was unconstitutional.
“I am sure that many in the profession are watching in horror at what Perkins Coie is going through,” the judge, Beryl A. Howell of the Federal District Court for the District of Columbia, said. She added, “It sends little chills down my spine.”
On Wednesday Judge Howell rejected a Trump administration motion that she recuse herself from the case. She said the disqualification motion was “rife with innuendo.”
Lauren Hirsch and Rob Copeland contributed reporting.