As a partner at Cadwalader, Wickersham & Taft, Wall Street’s oldest law firm, Todd Blanche had represented people close to President Trump over the years.
But in 2023, when Mr. Trump was facing multiple criminal investigations and Mr. Blanche wanted to represent him, most of the firm’s leadership balked at the idea, according to people with knowledge of the matter.
So, Mr. Blanche left Cadwalader, hanging out his own legal shingle and expressing bitterness to some allies that he had to do so to take on Mr. Trump as a client, one of the people said.
While Mr. Blanche’s loyalty earned him a reward — Mr. Trump appointed him deputy attorney general — Cadwalader is now bracing for some blowback.
As the White House ramps up its attacks on major law firms — imposing executive orders against some and striking deals with others — Cadwalader recently learned that it might become ensnared in Mr. Trump’s wide-ranging crackdown, according to four people with knowledge of the discussions.
One of Mr. Trump’s advisers has been in touch with the firm to suggest that it sign a deal in which it would offer tens of millions of dollars in pro bono legal services to causes that the Trump administration supports.
While Cadwalader was not explicitly threatened with an executive order, people briefed on the matter said, the implicit message encouraging a deal was clear: Sign, or face the possibility of an executive order that, no matter how unlikely it might be that it comes and however legally dubious, could nonetheless hobble the firm’s business.
In those discussions, Mr. Blanche’s split with the firm was not cited as the impetus for the outreach, and the precise reasoning behind it remained unclear. It was also unclear whether Cadwalader would ultimately reach a deal or face an order, and a spokesman for the firm declined to comment.
Cadwalader is hardly the only firm on Mr. Trump’s radar. Kirkland & Ellis, the nation’s largest firm by revenue, has had discussions with Mr. Trump’s advisers, a person with knowledge of the matter said.
And over the last two weeks, Skadden Arps, Willkie Farr & Gallagher, and Milbank met the Trump team’s demands, each promising to dedicate $100 million of pro bono work to causes that Mr. Trump supports and to represent clients no matter their political views. The deals enabled the firms to avoid an executive order.
The White House is working on a number of such deals with other firms, one person briefed on the matter said, and it is likelier that those would be announced first, even if Cadwalader ultimately agrees to one. Some firms might be announced together.
A White House spokesman did not respond to emails seeking comment. A Justice Department spokesman declined to comment.
Mr. Trump hit other firms with executive orders that jeopardized their ability to represent government contractors and limited their access to federal buildings. One of those firms, Paul Weiss, struck a deal with Mr. Trump. Three others have opted to fight in court, where federal judges have largely blocked the orders from taking effect for now.
While some of the firms have supported Mr. Trump’s political opponents, worked with prosecutors investigating him or hired lawyers who have been critical of the president, Cadwalader does not fall into any of those categories. It does, however, speak to Mr. Trump’s complaint that some big law firms were, for four years, reluctant to support polarizing conservative clients — in this case, Mr. Trump himself.
Lawyers who worked on the Trump legal team when he was a candidate, or who represented some of his many advisers swept up in various investigations, almost uniformly say that they unjustly became pariahs in the legal and business communities for their connections to Mr. Trump. Big law firms, they said, feared reprisals from Democrats or that clients would leave if they worked with Mr. Trump.
But those decisions were made by businesses, not the White House using presidential power to enforce those measures.
And officials at many major firms privately said they did not want to take Mr. Trump on as a client because for years, including during his first presidency but also well before it, he refused to follow any kind of conventional legal advice. Many of those firms’ other clients considered Mr. Trump’s behavior leading up to the attack on the Capitol by a mob of his supporters on Jan. 6, 2021, to be a true threat to democracy.
Given Mr. Trump’s history of stiffing firms that worked for him, many top officials at major firms were also worried that they would not get paid for their work.
Despite not taking on Mr. Trump as a client, Cadwalader had previously not shied away from representing his aides and allies.
The firm represented several Trump business associates, including Allen H. Weisselberg, the longtime chief financial officer at Mr. Trump’s family company. And when Mr. Blanche was at the firm, he defended Paul Manafort, who was Mr. Trump’s 2016 campaign chairman. Mr. Blanche also represented Boris Epshteyn, an outside legal adviser to Mr. Trump who has remained a powerful figure with the president.
Mr. Weisselberg pleaded guilty in a financial fraud case and served a brief jail sentence. Mr. Blanche successfully got a New York-based case against Mr. Manafort dismissed. Mr. Epshteyn was not among the people charged in the investigations in which Mr. Blanche represented him.
Mr. Epshteyn has been closely involved in Mr. Trump’s efforts to tighten his grip on a wide number of firms. And although it is unclear who in Mr. Trump’s orbit initiated the recent contact with Cadwalader, Mr. Epshteyn was involved in those discussions, according to people with knowledge of the matter.
Mr. Epshteyn, who oversaw the legal team managing Mr. Trump’s various lawsuits and criminal cases over the last four years, helped bring Mr. Blanche on as the lead lawyer for Mr. Trump.
In the New York criminal case in which Mr. Blanche defended Mr. Trump, the jury ultimately convicted Mr. Trump of falsifying business records to cover up a sex scandal. But under a strategy that Mr. Epshteyn and Mr. Blanche worked on with the rest of the team, Mr. Trump’s sentencing in that case was postponed after he was elected president again in November.
Ten days before Mr. Trump took office again in January, the judge in the case granted him an unconditional discharge, which was effectively no sentence at all.
Devlin Barrett and Matthew Goldstein contributed reporting. Susan C. Beachy contributed research.
