• A federal judge appeared impatient with a DOJ lawyer defending a Trump Big Law executive order.
• Jenner & Block asked a judge to permanently block the order, saying it was illegally targeted.
• A Justice Department lawyer struggled to come up with legal rationales at a Monday hearing.

A federal judge appeared poised to hand Big Law another win after he snapped Monday at a Justice Department lawyer attempting to justify President Donald Trump's executive order targeting one firm.

During Monday's court hearing, Richard Lawson, the Justice Department attorney, argued that Trump's order could not possibly be illegal because it required federal agencies to act "consistent with applicable law."

Lawson appeared to struggle through arguments, at times not giving direct responses to questions from the judge.

Lawson said Trump could target Jenner & Block, the Big Law firm, because the president said "Jenner discriminates against its employees based on race" — even though no court or government agency had come to that conclusion.

"Give me a break," US District Judge John Bates snapped, as Lawson said federal agencies should be allowed to follow the order because the firm engaged in "racial discrimination."

The oral arguments, in a Washington, DC, federal court, were part of Jenner & Block's lawsuit seeking to permanently block Trump's March 25 executive order targeting the firm. Bates previously ordered the federal government to pause the implementation of Trump's order.

Jenner & Block, represented by the elite law firm Cooley LLP, is one of four firms that sued the government seeking to stop Trump's executive orders. Nine other Big Law firms all made deals with Trump, collectively promising nearly $1 billion in pro bono work, to avert orders targeting them.

The law firms fighting the Trump administration, so far, are winning. Federal judges have swiftly issued temporary restraining orders preventing the executive orders from going into effect. And in court hearings for other cases, federal judges have been similarly impatient with Lawson's arguments, Business Insider reported Sunday.

During one hearing last week, for the law firm Perkins Coie's lawsuit seeking to stop an executive order, a judge referred to some of the Justice Department's positions as "hyper-technical legal arguments that may have no merit."

'A pretty strange reading'

Bates, an appointee of former President George W. Bush, appeared impatient Monday as he questioned Lawson over the legal basis for Trump's order.

Trump, in the first section of the order, said he targeted Jenner & Block in part because the firm previously hired a lawyer who worked for former Justice Department Special Counsel Robert Mueller, among other reasons.

The order would strip Jenner & Block employees of security clearances, cancel any contracts with the firm and its clients, and ban all employees from government buildings and from meeting with government officials.

"Ordering guidance specific to Jenner & Block that limits access to federal buildings, access to federal employees, access to federal agencies — the rationales in Section One that warrant that are what? Are what?" Bates asked Lawson.

In court filings and in Monday's hearing, Lawson has argued that judges should give broad leeway to Trump's power to target people and companies through executive orders, especially for purported national security issues.

Lawyers for Jenner & Block say the order is effectively government retaliation for free speech, violating the First Amendment. They also say Trump's order would violate their clients' right to counsel, as well as Jenner & Block's obligation to advocate on behalf of their clients without government interference.

The law firm argues that the order would also effectively kick several Jenner & Block lawyers out of their military reserve service because that service depends on their having security clearances.

Lawson said federal agencies would review security clearances on "an individual-by-individual basis" rather than issuing a blanket suspension of everyone at the firm to remain "consistent with applicable law."

Bates said he found that to be "a pretty strange reading" of the executive order.

"You think an agency official, given this executive order, is going to say, 'Well, I'm going to do a person-by-person analysis to decide whether I will suspend the security clearances of these seven Jenner people subject to my agency,'" the judge asked incredulously. "Is that what you think?"

Bates also reserved sharp questions for Jenner & Block's attorney, Michael Attanasio, during the hearing.

He asked whether it was necessary to strike down the entire executive order, or just the parts that directly harmed the law firm.

Attanasio asked the judge to issue a permanent injunction against the entire order, much like Trump withdrew the executive order he issued for Paul Weiss, which struck a deal with the president. The lawyer said Trump issued the order against Jenner & Block as "retribution."

"It was set up to be one form of punishment, and it should be taken down the same way, just as the President did for Paul Weiss," Attanasio said. "The difference being this time it gets taken down not on bended knee, but because this court enforces the constitution."

Bates said a written opinion in the case was "forthcoming."

Correction: April 28, 2025 — An earlier version of this story misstated the amount of pro bono work the nine other firms collectively promised. It is nearly $1 billion, not $1 trillion.

• Prosecutors want to seal Sean Combs' "freak off" videos in sex-trafficking trial.
• Combs is accused of sex trafficking and racketeering, with Cassie Ventura as a key victim.
• The judge is hammering out resolutions for different legal issues before the trial in May.

Prosecutors want to make sure the public doesn't see the "freak off" videos made by Sean "Diddy" Combs, which they say they'll present as exhibits in his upcoming criminal sex-trafficking trial.

Even the audio from those videos shouldn't reach the ears of the public and the press, argued Assistant US Attorney Madison Smyser in a court conference on Friday.

"These are extremely sensitive videos, they are going to involve videos of 'freak offs,'" Smyser said. "They involve other parties, victims, and, in some videos, Mr. Combs."

Smyser said prosecutors and defense lawyers were working out a way so that only jurors would be able to see and hear the videos when they're presented in court.

The indictment, brought by federal prosecutors in Manhattan, accuses Combs of sex trafficking and racketeering.

The primary victim prosecutors identified is Cassie Ventura, who was in a romantic relationship with Combs for 10 years. According to prosecutors, Combs sexually abused Ventura through "freak offs," which they described as elaborate and lengthy sexual performances that Combs staged, masturbated during, and often recorded.

Prosecutors have identified another four accusers who are expected to testify as victims in the trial. The judge has also allowed one "propensity witness," a yet-identified former romantic partner who is set to testify by name about alleged prior abuse, but who is not considered a victim in the criminal charges. Some of the witnesses are also expected to include sex workers who were recruited for the "freak offs."

Combs was attentive during Friday's court conference, the penultimate one before jury selection begins on May 5.

The hip-hop artist wore khaki jail garb and what appeared to be laceless Vans slip-on shoes.

Before the start of the hearing, Combs hugged his three female attorneys and then shook hands with one of his male lawyers. Throughout the conference, he sipped water from an unusually small plastic cup on the defense table before him.

US District Judge Arun Subramanian, who is overseeing Combs' criminal case, asked prosecutors to provide legal justifications for sealing the "freak off" videos, which would become court records if they were to be entered into evidence.

Prosecutors said they'd file a letter providing examples where similar procedures were followed in other cases. In R. Kelly's trial in Brooklyn, the court had jurors watch videos of sexual abuse on small screens in front of their jury seats while wearing earphones, while journalists and members of the public were kept out of the courtroom.

A victim's 'medical procedure'

During Friday's hearing, prosecutors also said they wanted an accuser to testify about a "medical procedure" that they said was a result of a "freak off."

Combs's defense attorneys argued that the procedure wasn't sufficiently related to the conduct described in the indictment, and that the accuser shouldn't be able to testify about the experience.

Submaranian ultimately concluded that he'd wait and see what else the victim would testify about before deciding if prosecutors could ask questions about the purported medical procedure.

The judge also issued a ruling narrowing the scope of what Dawn Hughes, an expert on interpersonal relationships, would be allowed to testify about. Hughes, who previously testified in the trial between Johnny Depp and Amber Heard, and is expected to testify in Harvey Weinstein's ongoing trial, is expected to testify on behalf of Combs. Combs's lawyers have said she would partly testify about the "swingers" lifestyle the singer participated in.

Subramanian previously resolved most of the other legal issues ahead of the trial, which is set to take place in the same lower Manhattan courtroom where Combs's jailmate Sam Bankman-Fried had his trial.

The judge allowed Combs's team to obtain drafts of Ventura's memoir for cross-examination, but did not allow them to obtain other notes, emails, or bank records they had requested.

Subramanian also forced Warner Bros. to give Combs' lawyers interview footage with two accusers taken for a Max documentary, "The Fall of Diddy." An attorney for Combs said in Friday's hearing that they expected to receive the footage next week.

The contents of Ventura's memoir have never been made public, and little information about it is known.

Combs's lawyer Marc Agnifilo discussed the memoir in a September court hearing, where he unsuccessfully asked a judge to allow Combs to stay out of jail ahead of the criminal trial.

Agnifilo said Combs and Ventura had a consensual, if complicated, 10-year relationship, and that she essentially tried to extort him with the memoir draft after it ended. In November 2023, Combs settled a civil sexual abuse lawsuit that Ventura brought against him.

"'My client has written a book, and she is going to publish it, but if you want to buy the rights, then you will have the exclusive rights, and she won't be able to publish it.'" Agnifilo said, characterizing an offer from one of Ventura's previous lawyers. "'And you know what, you can buy the rights for $30 million.'"

Later, Ventura retained a different lawyer and sued Combs under New York's Adult Survivors Act, alleging sexual abuse,

"'I am not really here to embarrass you anymore to the tune of $30 million; I am going to bring this civil sex claim against you,'" Agnifilo said, purportedly quoting Ventura's other attorney.

Agnifilo's arguments were not successful. Combs has been detained in Brooklyn's Metropolitan Detention Center since September.

• President Donald Trump has issued a wave of executive orders targeting high-profile law firms.
• Trump has restricted clearances — ultimately limiting the way they do business — for firms that have clashed with his administration.
• While some firms have agreed to Trump's demands, others have sued the administration.

As Donald Trump has taken aim at Big Law law firms in recent weeks, some firms have made deals with the president, while others are refusing to throw in the towel.

The president's wide-reaching orders have prompted reviews of each firm's government contracts, canceling security clearances for some firm employees and, in some cases, blocking them from entering federal buildings — including courthouses.

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. Several firms have alleged in lawsuits that the executive orders intended to chill free speech and deter clients from doing business with them. Others have agreed to work with the administration to avoid punitive executive actions against them.

The president has singled out a string of law firms that he says have wronged him in some capacity, have worked with his political opponents, or have had diversity initiatives that are counter to his anti-DEI efforts.

What's more, Trump instructed Attorney General Pam Bondi to identify firms with "frivolous" cases against the administration so that they could be targeted for further executive action.

Whether they're on the ropes or down for the count, here are the firms Trump is taking on, how they've responded, and where the legal process stands for those who have challenged him 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.

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."

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."

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."

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 signed an order naming Jenner & Block on March 25 that revoked security clearances from the firm's attorneys and ordered a review of the firm's contracts with the federal government.

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.

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."

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 immediately suspends any Susman security clearances held by the firm's employees. The federal government will 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."

Susman said it would fight Trump's order.

"Anyone who knows Susman Godfrey knows we believe in the rule of law, and we take seriously our duty to uphold it," the firm said in a statement to Business Insider. "This principle guides us now. There is no question that we will fight this unconstitutional 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.

"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.

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, combatting 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 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.

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.

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.

Latham & Watkins did not respond to a request for comment.