Robert Giuffra, the head of one of the country’s most powerful law firms, was headed to the gym when he got an unexpected phone call.
When Giuffra picked up, the president of the United States was on the other end.
Donald Trump was in an Oval Office meeting with Paul Weiss chairman Brad Karp, whom Giuffra considered a personal friend.
Five days earlier, Trump issued an executive order that would have stripped security clearances from Paul Weiss lawyers and limited their access to government property. As Karp later described, the deal “could easily have destroyed” the firm. In that March 19 Oval Office meeting, Karp wanted a way out, according to five people familiar with the meeting. Could Giuffra — Trump’s personal lawyer — help?
Privately, Giuffra had expressed concerns about the order, seemingly worried about its implications for the legal industry, according to two people. Over the next day, Giuffra helped hash out an agreement between Trump and Paul Weiss: the law firm pledged tens of millions in pro bono work toward Trump’s political priorities, and Trump rolled back the executive order.
The phone call drew Giuffra deeper into an ethical drama familiar to many Trump lawyers: the blurring of lines between government work, the president’s priorities, and the law itself.
This time, the stakes are higher. Giuffra isn’t an outsider lawyer plucked from obscurity like Alina Habba or a longtime political ally like Rudy Giuliani. He leads one of the most powerful law firms in America.
As the chair of Sullivan & Cromwell, Giuffra is a titan of the legal industry. The 146-year-old firm made $2 billion in revenue last year, and its highly paid lawyers have represented the likes of OpenAI in its partnership with Microsoft and Discover in its merger with CapitalOne, and participated in the thorny bankruptcy of FTX.
Giuffra, with no official role in the White House, was weighing in on how the president of the United States used the powers of his office to subjugate a rival law firm.
The art of the deal
The Giuffra-negotiated deal between Trump and Karp to roll back the March 14 executive order stunned and divided the legal profession.
It also became a template. Following Paul Weiss, eight firms agreed to deals with the president, collectively pledging over $900 million in free work to advance his policies. The deals have introduced myriad logistical and ethical legal issues; it’s not even clear if they’re legal, and no one has publicly said how their terms are supposed to be enforced.
Four other firms, all targeted by executive orders, chose to fight and won court rulings blocking the president’s decrees.
Sullivan & Cromwell has been spared either fate, thanks in part to Giuffra’s deft hand.
Shortly after Trump’s second inauguration, Giuffra announced that the firm would represent the president in two appeals: a Manhattan criminal conviction and a half-billion dollar judgment over falsified tax and bank loan documents from the Trump Organization.
At the same time, Giuffra has helped Trump collapse the distinction between the presidency and personal matters. During the negotiations with Paul Weiss, Giuffra didn’t appear to draw any distinction between his role as Trump’s personal lawyer and as someone who was weighing in on how Trump would use his presidential powers, one person familiar with the negotiations told Business Insider.
Shortly after Trump issued the executive order, Karp brought on Bill Burck, one of the leaders at the firm Quinn Emanuel, to represent Paul Weiss in suing the administration. Burck engaged with people working in the White House, including the White House Counsel’s office, to determine whether they could reach a resolution, a person familiar with the discussions said.
But Giuffra — along with Trump’s personal senior counsel, Boris Epshteyn — took over the negotiations several days later, without any apparent involvement from White House lawyers, according to the person. Giuffra acted as an intermediary between Epshteyn and Burck in the discussions, two people said.
A spokesperson for Sullivan & Cromwell said Giuffra served as a go-between, helping “the Administration and Paul Weiss reach a mutually acceptable resolution.” A spokesperson for Paul Weiss declined to comment on the record.
The White House referred questions to Epshteyn, who declined to comment for this story.
The blurred lines raise “very severe issues of ethics and professional responsibility,” according to Harold Koh, a law professor who served as the top State Department lawyer in the Obama administration.
Epshteyn and Giuffra played a role in how Trump should use his government powers. But as Trump’s personal lawyers, rather than government employees, it’s not clear if they’re acting on behalf of the people of the United States, or on behalf of Trump’s personal interests, Koh said.
“Government lawyers should do the government’s business and personal lawyers should deal with personal matters,” Koh added. “And the fact that we can’t tell whether these lawyers are operating in official or personal capacity shows why they’re so problematic.”
The betrayal
Despite Giuffra’s hope that the deal would ultimately help his industry, it created public friction between two of its most powerful figures.
Karp and Sullivan & Cromwell have each been telling slightly different stories about how the deal came to be. The firms can’t even agree on when Giuffra became involved, itself a sign of how blurred the lines had become between Trump’s personal and official business.
In Sullivan & Cromwell’s telling, Paul Weiss — rather than Trump — initiated Giuffra’s involvement. Giuffra’s involvement was a personal favor for a peer firm, not part of his representation of Trump.
According to a letter Sullivan & Cromwell partner Sharon Nelles sent to Congress, Giuffra contacted people within the Trump administration after he “received an outreach on behalf of” Paul Weiss on March 15, a day after the executive order, to help reach a deal.
Karp, meanwhile, has said he was unaware of Giuffra’s involvement until March 19. On that day, Karp met with Trump in the Oval Office, and Trump dialed Giuffra into the meeting, according to three people familiar with the negotiations.
Trump announced the deal on March 20 and rescinded the executive order the next day.
Giuffra had believed he was offering Karp and Paul Weiss a boon, according to one of the people familiar with the deal.
Instead of being treated as a peacemaker, Giuffra found Sullivan & Cromwell under attack.
He was hurt by the publication of a story in the New York Times, published several days after the deal, reporting that Karp felt pressured to make a deal because rival firms — including Giuffra’s — were trying to snap up its partners and clients. Giuffra fumed that Paul Weiss insiders had thrown his and other firms under the bus to try to justify their deal.
In a letter to Congress, a Sullivan & Cromwell partner said many lawyers at the two firms were “law school classmates, neighbors, former partners and longtime friends and colleagues” and denied the firm had tried to “poach” anyone from Paul Weiss.
In a March 23 letter to employees explaining the deal, Karp said he was dismayed that other law firms had not rallied to Paul Weiss’s side. Instead, he wrote, “certain other firms were seeking to exploit our vulnerabilities by aggressively soliciting our clients and recruiting our attorneys.”
The president’s lawyer
In his second term, Trump has demonstrated his confidence in Sullivan & Cromwell, and there’s no doubt the firm has benefitted.
In the same Truth Social post where he designated several of his personal lawyers to high-ranking Justice Department positions, he also named Sullivan & Cromwell lawyer Jay Clayton to lead the US Attorney’s office for the Southern District of New York. And in May, Giuffra filed papers to represent the president, Donald Trump Jr., Eric Trump, and the Trump Organization itself in the civil fraud case.
Still, Giuffra and his firm are engaged in a delicate dance. Trump has churned through a number of lawyers over the years. More than a dozen, after acting on Trump’s behalf, have been disbarred or sanctioned. Even more have been bench-slapped by judges in hearings and trials.
Trump’s second term is already claiming casualties. Eric Trump fired Burck from his role as an outside ethics counsel for the Trump Organization in April after the lawyer agreed to represent Harvard University, which Trump has also targeted with executive orders.
Giuffra isn’t staking just his own reputation on working for Trump. Since Trump became involved in politics, elite law firms have typically shunned him. Todd Blanche, his lead lawyer in most of his criminal cases, quit Cadwalader, Wickersham & Taft to represent Trump after the firm’s leadership disapproved of taking him on as a client.
In embracing Trump, Sullivan & Cromwell, with its 900 attorneys and high-profile client list, is marking a different path for Big Law.