President Donald Trump has taken aim at Big Law in recent months. Some law firms struck deals with the president, while others instead chose to challenge his orders in court.
Trump has accused the Big Law firms — including Paul Weiss, Perkins Coie, and Covington & Burling, among others — of weaponizing the judicial system. His orders have, in turn, made it harder for the firms to continue conducting business as usual, ordering reviews of each firm’s government contracts, canceling security clearances for some employees, and, in certain cases, blocking them from entering federal buildings, including courthouses.
Several firms have alleged in lawsuits that the executive orders intended to chill free speech and deter clients from doing business with them. So far, many of the firms that have fought back are winning in court.
Still, other firms agreed, at times preemptively, to work with the administration to avoid punitive executive actions against them. Several of these firms have seen high-profile resignations in response, and faced criticism from others in the industry for their refusal to challenge the legality of the orders.
The law firms that the president has singled out are those that he says have wronged him in some capacity, typically by representing his political opponents, or those that have implemented diversity initiatives in their hiring practices that are counter to his anti-DEI efforts.
In addition to the initial executive orders, Trump has also instructed Attorney General Pam Bondi to identify firms with “frivolous” cases against the administration so that they could be targeted for further punitive action.
Whether they’ve challenged the administration or struck a deal, here are the firms Trump is taking on, how they’ve responded, and where the legal process stands for those who have fought back in court.
Paul Weiss
On March 14, Trump issued an executive order directed at the prominent New York City-based law firm Paul Weiss, where he railed against the attorney Mark Pomerantz and decried what he said was “unlawful discrimination” from diversity, equity, and inclusion initiatives at the firm.
Pomerantz previously left Paul Weiss to aid the Manhattan District Attorney’s office as it probed Trump’s finances. When Pomerantz resigned as special district attorney in February 2022, he wrote in a departing letter that he believed Trump was “guilty of numerous felony violations.”
In the order, Trump sought to revoke security clearances and bar access to government buildings for attorneys of the firm. Such a sweeping directive could also include federal courthouses, a scenario that would be detrimental to the firm’s work.
However, Trump just days later rescinded the executive order and announced an agreement with Paul Weiss chairman Brad Karp. Trump said the firm would provide $40 million in pro bono work for causes that the administration supports and end its DEI policies.
Karp received a heap of criticism, with many questioning why Paul Weiss didn’t challenge Trump’s order. In an email to the firm’s attorneys, he said there was a desire from the outset to challenge the directive. In the same email, though, Karp argued that even if Paul Weiss won in court, it would become “persona non grata” with the Trump White House, which could prompt a wave of clients to switch to other firms and subsequently threaten the viability of the firm.
“It was very likely that our firm would not be able to survive a protracted dispute with the administration,” Karp wrote in the email.
On May 23, four top partners at the white-shoe firm — Karen Dunn, a star litigator who has helped Democratic candidates prepare for presidential debates, her longtime partners Bill Isaacson and Jessica Phillips, and the former prosecutor Jeannie Rhee — announced that they would be leaving Paul Weiss to start their own firm.
Perkins Coie
On March 6, Trump targeted the law firm Perkins Coie, issuing an executive order to suspend the security clearances of the firm’s attorneys and criticizing its diversity and inclusion policies.
In the order, Trump called out what he said was the firm’s “dishonest and dangerous activity.”
The president, in his order, highlighted the firm’s representation of former Secretary of State Hillary Clinton — his rival in the 2016 presidential election — during that year’s tumultuous campaign.
However, Perkins Coie struck back, filing a lawsuit against the administration for actions that it said “violates core constitutional rights, including the rights to free speech and due process.”
“At the heart of the order is an unlawful attack on the freedom of all Americans to select counsel of their choice without fear of retribution or punishment from the government,” Perkins Coie managing director Bill Malley said in a statement in March. “We were compelled to take this action to protect our firm and our clients.”
The day after Perkins Coie filed its suit, a federal judge agreed to temporarily block part of the president’s executive order.
Perkins Coie, in a statement, said the ruling was “an important first step in ensuring this unconstitutional Executive Order is never enforced.”
On May 2, US District Judge Beryl Howell, in a scathing ruling, struck down President Donald Trump’s executive order against Perkins Coie, declaring his effort to target the Big Law firm unconstitutional.
“Eliminating lawyers as the guardians of the rule of law removes a major impediment to the path to more power,” Howell wrote in her ruling. “In a cringe-worthy twist on the theatrical phrase ‘Let’s kill all the lawyers,’ EO 14230 takes the approach of ‘Let’s kill the lawyers I don’t like,’ sending the clear message: lawyers must stick to the party line, or else.”
A spokesperson for Perkins Coie told Business Insider in a statement that the firm was pleased with the judge’s ruling.
“This ruling affirms core constitutional freedoms all Americans hold dear, including free speech, due process, and the right to select counsel without the fear of retribution,” the statement said. “As we move forward, we remain guided by the same commitments that first compelled us to bring this challenge: to protect our firm, safeguard the interests of our clients, and uphold the rule of law.”
Covington & Burling LLP
Trump on February 25 signed a memorandum to evaluate federal contracts and direct the suspension of security clearances for some employees at Covington & Burling, a DC-based law firm known for its antitrust work.
The president in the memo said he was suspending the clearances of individuals who advised former special counsel Jack Smith.
Smith brought two federal cases against Trump — one for election interference in the 2020 presidential election and the other for retaining classified documents — but both were dropped after the president won reelection to a second term in November 2024.
In the memo, Trump went after individuals whom he said were “involved in the weaponization of government” and named Peter Koski, a lawyer at Covington representing Smith.
A Covington spokesperson in March said it was representing Smith in an “individual” capacity.
“We recently agreed to represent Jack Smith when it became apparent that he would become a subject of a government investigation,” the spokesperson said in a statement. “We look forward to defending Mr. Smith’s interests and appreciate the trust he has placed in us to do so.”
The firm has not taken any public action against the administration in response to the executive order against it.
Skadden, Arps, Slate, Meagher & Flom LLP
Skadden made a deal with Trump, acting before it was singled out in any executive orders. The firm promised to provide $100 million in pro bono legal services “to causes that the President and Skadden both support,” Trump announced on March 28.
Skadden also affirmed its commitment to merit-based hiring and employee retention, Trump said. The firm also agreed that it would refrain from engaging in “illegal DEI discrimination,” according to a copy of the agreement that Trump shared on Truth Social.
In a statement, Jeremy London, Skadden’s executive partner, said the firm “engaged proactively” with the administration to reach the agreement.
“We firmly believe that this outcome is in the best interests of our clients, our people, and our Firm,” London said.
Speaking from the White House, Trump referred to the deal as “essentially a settlement.”
Within the firm, some associates and employees expressed frustration about the deal, calling it the beginning of the end for Skadden.
In the weeks leading up to the agreement, Skadden associate Rachel Cohen publicly resigned and circulated an open letter among associates at top firms calling out their employers for what she has described as inaction in the face of the administration’s attacks.
After the deal was announced, another employee, Brenna Frey, also resigned publicly in an announcement on LinkedIn.
Elias Law Group
The chair of Elias Law Group took a different approach after it was targeted by the administration.
Trump named the Elias Law Group in his “frivolous” lawsuits memo, formally titled “Preventing Abuses of the Legal System and the Federal Court.”
It claimed that the law firm was “deeply involved in the creation of a false ‘dossier’ by a foreign national designed to provide a fraudulent basis for Federal law enforcement to investigate a Presidential candidate in order to alter the outcome of the Presidential election.”
The memo went on to say that the firm “intentionally sought to conceal the role of his client — failed Presidential candidate Hillary Clinton — in the dossier.” However, the memo did not order security clearance revocations or contract reviews as similar orders against other major law firms did.
Marc Elias, the Democratic election lawyer who founded and chairs the group, released a statement swinging back at Trump, whose actions target “every attorney and law firm who dares to challenge his assault on the rule of law,” he said.
“President Trump’s goal is clear,” Elias said in the statement. “He wants lawyers and law firms to capitulate and cower until there is no one left to oppose his Administration in court.”
Adding that American democracy is in a state of “peril,” Elias said his law firm would not cower.
“Elias Law Group will not be deterred from fighting for democracy in court,” he said. “There will be no negotiation with this White House about the clients we represent or the lawsuits we bring on their behalf.”
Jenner & Block
Trump on March 25 signed an order targeting Jenner & Block, revoking security clearances from the firm’s attorneys, and ordering a review of the firm’s contracts with the federal government.
Related stories
Business Insider tells the innovative stories you want to know
Business Insider tells the innovative stories you want to know
Trump’s order singled out Andrew Weissmann, a former Jenner attorney who Trump accused of building his career around “weaponized government and abuse of power.” Weissmann was a lead prosecutor in Robert Mueller’s Special Counsel’s Office, which investigated Trump’s 2016 presidential campaign and its ties to Russia.
Jenner issued a statement calling the order an “unconstitutional executive order that has already been declared unlawful by a federal court.”
“We remain focused on serving and safeguarding our clients’ interests with the dedication, integrity, and expertise that has defined our firm for more than one hundred years and will pursue all appropriate remedies,” the statement from Jenner said.
Jenner also fought back with a lawsuit. The firm is represented by Cooley LLP, a liberal-leaning firm that has hired lawyers from Democratic administrations.
On March 28, Judge John D. Bates of the US District Court for the District of Columbia issued a temporary restraining order that keeps the Trump administration from taking action against Jenner. On April 1, Bates extended this order until a final judgement has been made. Both the Justice Department and Jenner consented to the extension.
Following the ruling, Jenner said in a statement that the order holds “no legal weight.”
“We will continue to do what we have always done, our job as lawyers and fearless advocates for our clients,” the firm said.
On May 23, Judge Bates said Trump’s order against Jenner & Block retaliated against the firm for protected speech, striking it down in its entirety and declaring it unconstitutional.
“The order raises constitutional eyebrows many times over. It punishes and seeks to silence speech ‘at the very center of the First Amendment,'” Judge Bates, of the District Court of DC wrote in his ruling, adding that Trump’s order did so “via the most ‘egregious form of content discrimination — viewpoint discrimination,'” and “in an unacceptable attempt to ‘insulate the Government’s laws from judicial inquiry.'”
A spokesperson for Jenner & Block directed Business Insider to their public statement following the ruling, which said that the firm is “pleased with the court’s decision to decisively strike down an unconstitutional attack on our clients’ right to have zealous, independent counsel and our firm’s right to represent our clients fully and without compromise.”
“Our decision to fight the executive order in court is rooted in Jenner & Block’s history and values: we fiercely advocate for our clients under all circumstances,” the firm’s statement continued. “This ruling demonstrates the importance of lawyers standing firm on behalf of clients and for the law. That is what Jenner will continue to do for our clients — paying and pro bono — as we look to put this matter behind us.”
WilmerHale
The Trump administration has also targeted WilmerHale, which employed Mueller and other lawyers who worked with the Justice Department to investigate ties between Russia and Trump’s 2016 campaign.
On March 27, Trump signed an executive order that suspended security clearances for WilmerHale employees and limited their access to federal buildings. The order also revoked WilmerHale’s government contracts for engaging in “partisan representations to achieve political ends” and “efforts to discriminate on the basis of race.”
In contrast with other firms that have inked deals with the president, WilmerHale filed a lawsuit.
The firm hired Paul Clement, the conservative legal superstar of the firm Clement & Murphy, to fight back against the Trump administration.
“This lawsuit is absolutely critical to vindicating the First Amendment, our adversarial system of justice, and the rule of law,” Clement told Business Insider in a statement.
On the afternoon of March 28, Judge Richard J. Leon of the US District Court for the District of Columbia approved a motion for a temporary restraining order to halt executive actions against WilmerHale.
“There is no doubt this retaliatory action chills speech and legal advocacy, or that it qualifies as a constitutional harm,” Leon wrote.
A spokesperson for WilmerHale called the executive order unconstitutional and praised the court’s “swift action.”
WilmerHale was handed a legal victory on May 27 after Judge Leon struck down the order in its entirety, saying that the executive order was a form of “coercion” against the firm to “suppress WilmerHale’s representation of disfavored causes and clients.”
“I have concluded that this Order must be struck down in its entirety as unconstitutional,” Judge Leon wrote. “Indeed, to rule otherwise would be unfaithful to the judgment and vision of the Founding Fathers!”
“The Court’s decision to permanently block the unlawful executive order in its entirety strongly affirms our foundational constitutional rights and those of our clients,” a spokesperson for WilmerHale told Business Insider. “We remain proud to defend our firm, our people, and our clients.”
Harrison Fields, principal deputy press secretary, told Business Insider in a statement that the White House opposes Judge Leon’s ruling.
“The decision to grant any individual access to this nation’s secrets is a sensitive judgment call entrusted to the President,” Fields said. “Weighing these factors and implementing such decisions are core executive powers, and reviewing the President’s clearance decisions falls well outside the judiciary’s authority.”
While the federal government can appeal Judge Leon’s decision, in which case the proceedings will be heard in the court of appeals, no appeal has yet been announced.
Milbank
On April 2, Trump announced on Truth Social that he had struck a preemptive deal with Milbank without targeting the firm for executive action.
The terms of the deal, according to the president’s announcement, include the firm’s agreement to end any DEI-based hiring practices, and to perform at least $100 million worth of pro bono legal work to advance causes supported by the Trump administration, such as “assisting veterans” and “combatting antisemitism.”
In addition, Milbank’s pro bono committee will ensure the firm takes on cases representing “the full political spectrum, including Conservative ideals,” and commits that it “will not deny representation to clients” based on the personal political views of individual lawyers, per Trump’s announcement.
“Milbank LLP approached President Donald J. Trump and his Administration, stating their resolve to help end the Weaponization of the Justice System and the Legal Profession,” reads a statement from the White House included in Trump’s post. “The President continues to build an unrivaled network of Lawyers, who will put a stop to Partisan Lawfare in America, and restore Liberty and Justice FOR ALL.”
Milbank’s chairman, Scott Edelman, said in a statement posted by Trump that, after a “constructive dialogue,” the firm was “pleased we were so quickly able to find common ground” with the administration.
When reached by Business Insider, a spokesperson for the firm provided a letter sent by Edelman to Milbank’s staff in which he said the agreement “is very much in Milbank’s interest.”
“The Administration’s expressed concerns about big law firms, and in some cases its entry of Executive Orders against particular firms, have created uncertainty for law firms like ours,” Edelman’s letter to staff reads. “With this agreement, we believe we have gone a long way to putting these issues behind us. But we have done so in a way that allows us to continue to focus on the Firm’s values and missions, including with respect to pro bono and our hope to foster an inclusive, non-discriminatory community where all of our members have an equal opportunity to succeed.”
Edelman added: “Having now reached an agreement with the Administration, we can continue to do what we do best — focus on providing the best possible advice, counseling and service to our clients.”
Susman Godfrey
On April 9, Trump signed an executive memorandum targeting Susman Godfrey, a specialized litigation firm.
In a fact sheet, the White House accused Susman of spearheading “efforts to weaponize the American legal system and degrade the quality of American elections.”
Trump’s order sought to immediately suspend any Susman security clearances held by the firm’s employees, “pending a review of whether such clearances are consistent with the national interest.” The federal government said it would also terminate any contracts with the firm.
The firm’s hiring practices will also be reviewed “to ensure compliance with civil rights laws against racial bias.”
On April 11, Susman filed a complaint against the Trump administration, arguing that Trump’s executive order was in violation of the Constitution.
“Unless the Judiciary acts with resolve—now—to repudiate this blatantly unconstitutional Executive Order and the others like it, a dangerous and perhaps irreversible precedent will be set,” the complaint reads.
“If President Trump’s Executive Orders are allowed to stand, future presidents will face no constraint when they seek to retaliate against a different set of perceived foes. What for two centuries has been beyond the pale will become the new normal,” it adds.
A final decision in the case remains pending, although a judge has placed a restraining order preventing the implementation of Trump’s order.
Willkie Farr & Gallagher
Willkie Farr & Gallagher, which employs Doug Emhoff, husband of former Vice President Kamala Harris, struck a deal with the administration, pledging at least $100 million in pro bono legal work for conservative causes, Trump said in an April 1 social media post.
Related stories
Business Insider tells the innovative stories you want to know
Business Insider tells the innovative stories you want to know
“Willkie Farr & Gallagher LLP proactively reached out to President Trump and his Administration, offering their decisive commitment to ending the Weaponization of the Justice System and the Legal Profession,” the White House said, according to Trump’s post on Truth Social.
The firm’s ties to Trump go to the 1990s when it represented the then real estate developer in a bankruptcy case.
In 2023, Willkie brought Tim Heaphy as partner. Heaphy was the former chief investigative counsel for the congressional committee that investigated the January 6, 2021, attacks on the Capitol.
The firm also represents X, Elon Musk’s social media platform.
Trump said that Willkie Farr & Gallagher also committed to “Merit-Based Hiring, Promotion, and Retention,” which touches on the Trump’s efforts to dismantle DEI initiatives.
Wilkie Farr lost its longest-serving lawyer in April after Joseph Baio, a partner who’d worked there for 47 years, resigned over the firm’s preemptive deal with Trump, The New York Times reported.
A representative for Willkie Farr & Gallagher did not respond to a request for comment.
Cadwalader, Wickersham & Taft
Trump said in a Truth Social post April 11 that the administration had come to an agreement with Cadwalader, Wickersham & Taft, saying the law firm agreed to provide $100 million in pro bono legal services.
The services would go toward causes supported by Trump and the law firm, including assisting veterans and law enforcement, combating antisemitism, and “ensuring fairness in our justice system.”
The statement said the firm also agreed to “not engage in illegal DEI discrimination and preferences” or to deny legal representation “because of the personal political views of individual lawyers.”
“The substance of our agreement is consistent with the principles that have guided Cadwalader for over 230 years: We always put our client’s interests first; We believe that Justice should be available to everyone; and We are committed to attracting, retaining and nurturing the very best talent from all backgrounds,” Patrick Quinn, managing partner at Cadwalader, said in a statement shared by Trump.
Cadwalader did not respond to a request for comment.
Kirkland & Ellis
Trump also announced on April 11 that the administration had come to an agreement with an additional four law firms, including Kirkland & Ellis. The president said in a Truth Social post the firms agreed to provide a total of $500 million in pro bono legal services to go toward the same types of causes, with each firm contributing $125 million.
The firms also agreed to engage outside counsel to oversee their hiring practices and ensure they comply with antidiscrimination laws.
Trump said as a result of the agreement, he would end an Equal Employment Opportunity Commission investigation into the law firms over their DEI practices, which was initially announced on March 17.
In a joint statement shared by Trump, the senior executives at the four law firms said: “We have resolved this matter while upholding long-held principles important to each of our Firms: Equal Employment Opportunity; providing pro bono assistance to a wide range of underserved populations, and ensuring fairness in the Justice System; and representing a broad spectrum of clients on various matters.”
In a firm-wide internal memo obtained by BI, the Kirkland & Ellis executive committee said the agreement “resolves the EEOC’s investigation, including its broad request for information about our people and our clients, which we no longer will be required to provide, and we will not be the target of an executive order.”
“We made the decision to pursue this solution because at our very core our mission is to protect and support our people and our clients, and this agreement does both,” the memo said.
Jacqui Pittman, an associate at Kirkland, publicly resigned after the deal was announced.
A&O Shearman
A&O Shearman was among the law firms with which Trump said on April 11 that his administration had reached an agreement. The firm agreed to provide $125 million in pro bono legal services to causes supported by the administration. It also agreed to engage outside counsel to oversee its hiring practices, and the EEOC investigation into the firms has stopped.
A&O Shearman did not respond to a request for comment.
Simpson Thacher & Bartlett
Simpson Thacher & Bartlett also reached an agreement with the White House to provide $125 million in pro bono legal services to causes supported by the firm and Trump, as well as engage outside counsel to ensure its hiring practices comply with antidiscrimination laws.
As a result of the agreement, the EEOC investigation into the firm’s hiring practices was stopped.
Los Angeles-based attorney Siunik Moradian, an associate at the firm, resigned after the deal was announced. He told Business Insider he’d considered leaving Big Law since the Paul Weiss deal was announced and found “firms were a lot more willing to cut a deal than I thought.”
“I think what becomes really concerning for me is that these law firms are not making deals because of the strength of the Trump administration’s claims or potential claims,” he said. “They’re extra-legal extortionist tactics, and it just seems like a dangerous precedent and something that the Trump administration is going to add to their playbook of weaponizing the legal system in the courts.”
Simpson Thacher & Bartlett did not respond to a request for comment.
Latham & Watkins
Latham & Watkins was also among the four firms that reached an agreement with Trump, according to the April 11 announcement. The firm agreed to provide $125 million in pro bono legal services as well as engage outside counsel to oversee its hiring. As a result, the Trump administration ended the EEOC investigation into the firm.
Sam Wong, an associate at Latham, announced his resignation from the firm on LinkedIn following the announcement of the deal.
Latham & Watkins did not respond to a request for comment.
