How the Trump Administration Got $940 Million Without a Single Court Victory

Last updated 9 hours ago. Our resources are updated regularly but please keep in mind that links, programs, policies, and contact information do change.

Nine major law firms had already pledged a combined $940 million in pro bono legal services to Trump administration-approved causes. This happened before the Justice Department filed a brief notice with the U.S. Court of Appeals for the D.C. Circuit on March 2, 2026. The government was dropping its appeals in four cases where federal judges had struck down executive orders targeting Perkins Coie, WilmerHale, Jenner & Block, and Susman Godfrey. No explanation accompanied the filing. No White House statement. No substantive explanation from the Justice Department about why it was walking away from its own legal fight, though a DOJ spokesperson directed reporters to the filing when asked.

Most coverage framed it simply: the administration had lost. Courts had ruled. The rule of law had held.

That framing is accurate as far as it goes. But none of those nine firms settled because courts ordered them to. None had lost a legal battle. They had simply decided that settling was cheaper than fighting.

The administration never won in court. It didn’t need to.

What the Executive Orders Did

The first executive order targeting a law firm was issued against Covington & Burling, before the March 6, 2025 order against Perkins Coie, a Seattle-based firm that had represented Hillary Clinton’s 2016 campaign and had hired the research firm that hired Christopher Steele to produce the infamous dossier. The order accused the firm of “dishonest and dangerous activity” and directed federal agencies to suspend employee security clearances, terminate government contracts, and restrict building access.

Three more orders followed in rapid succession. On March 25, an order targeted Jenner & Block, which had employed Andrew Weissmann, a prosecutor on Robert Mueller’s Russia investigation. Two days later, an order went after WilmerHale, which had employed Mueller himself. On April 9, Susman Godfrey, a national trial firm headquartered in Houston, Texas, with offices in New York, Los Angeles, and Seattle, that had represented Dominion Voting Systems in its defamation case against Fox News, received its own order.

The pattern was clear: firms were being targeted for representing clients or employing lawyers who had, at some point, worked against Trump’s political interests.

The orders also cited diversity, equity, and inclusion policies and alleged racial discrimination as grievances, but their operative sections focused on security clearances, government contracts, and building access — not EEOC investigations.

The administration’s stated legal argument, however, was not simply retaliation. The White House framed the orders as legitimate exercises of procurement and contracting authority. The federal government, it argued, has wide discretion over which firms may access federal buildings, hold security clearances, and receive government contracts. It may tie that access to firms meeting standards of conduct in line with the public interest.

The orders cited specific alleged misconduct, including what the Perkins Coie order called “dishonest and dangerous activity” related to the Steele dossier. Supporters of this approach pointed to long-held executive authority over contractor relationships and argued that firms doing government work have always been subject to conduct requirements.

Four courts unanimously rejected these justifications, finding that the orders targeted protected First Amendment activity and that the procurement rationale was a pretext. But the administration’s core legal argument was this: executive control over government access is a legitimate policy lever. That was the argument courts had to address and defeat on the merits before issuing those injunctions.

Courts moved fast. U.S. District Judge Beryl Howell issued a temporary restraining order blocking parts of the Perkins Coie order six days after it was signed. She wrote that it cast “a chilling harm of blizzard proportions across the legal profession” — threatening not just one firm but the profession’s ability to take on unpopular clients. She also wrote that it “stigmatizes and penalizes a particular law firm and its employees due to the Firm’s representation of clients pursuing claims and taking positions with which the current President disagrees.”

Judge John D. Bates, ruling on the Jenner & Block order, found it violated the Constitution in two separate ways. He called it “doubly violative of the Constitution” for targeting both the clients the firm represented and the lawyers it employed. He wrote that the order “seeks to chill legal representation the administration doesn’t like, thereby insulating the executive branch from the judicial check fundamental to the separation of powers.”

Judge Richard J. Leon found that WilmerHale “faces crippling losses and its survival is at stake.” He also found that the order constituted “a staggering punishment for the firm’s protected speech” (meaning expression the First Amendment shields from government punishment). Judge Loren AliKhan issued a permanent injunction, a final court order blocking the executive order from ever taking effect, against the Susman Godfrey order. She wrote that it “threatens the independence of the bar — a necessity for the rule of law.”

Four judges. Four rulings. Unanimous on the constitutional violations.

None of the orders ever took full effect.

The Nine Firms That Settled Before Any Court Required It

While those four cases were moving through the courts, a separate negotiation was happening in boardrooms across the country. Nine other firms, watching what was happening, reached a different conclusion.

The first to move was Paul Weiss, Rifkind, Wharton & Garrison. Trump had signed an order against Paul Weiss on March 14, citing the firm’s former association with Mark Pomerantz, who had worked at the Manhattan District Attorney’s Office on a case involving Trump’s finances. Pomerantz had left the firm to join the Manhattan DA’s office, resigning from that role in February 2022; the precise date of his departure from Paul Weiss is not independently confirmed. No matter. On March 20, less than a week after the order was signed, Paul Weiss struck a deal.

The firm agreed to abandon its DEI initiatives and commit $40 million in pro bono legal services to causes the President and the firm both support (including the administration’s antisemitism task force and “other jointly agreed-upon projects”). It also agreed to issue a public statement that Pomerantz had committed “wrongdoing.” Pomerantz later disputed this characterization, saying he had done nothing wrong. In return, Trump revoked the order.

Then the pace accelerated. The table below shows how the settlements stacked up:

Sources: Wikipedia’s documentation of law firm targeting; Axios reporting on Big Law pro bono deals. Note: Several firms settled preemptively, before any executive order was issued against them.

Eight of the nine firms settled without any executive order ever being issued against them — not seven, as some early reporting suggested. Skadden’s executive partner Jeremy London said the firm was “pleased to have achieved a successful agreement with President Trump.” A senior associate at Skadden, Brenna Frey, resigned publicly within days. She posted on LinkedIn that she was leaving because of the settlement.

The math across all nine firms: roughly $940 million in pro bono legal services, all of it directed toward causes the administration approves. To put that in context: among firms that voluntarily report pro bono hours, the typical contribution runs between 2 and 4 percent of total attorney hours annually — a figure that may overstate the broader top-100 average. A $100 million pledge at market billing rates makes up a large share of a firm’s entire annual pro bono capacity. That capacity is now locked in advance to government-approved causes.

Every settlement contained language about “mutually agreed causes” or similar wording showing the administration had input into which cases and causes the firms would work on. The exact details were deliberately vague, and the full settlement agreements were not made public. Because so little was disclosed, legal scholars at Lawfare noted the agreements were riskier than they appeared. The terms were kept secret, which contributed to that assessment.

The Four Firms That Won in Court and the Nine That Didn’t Fight

Here is the uncomfortable arithmetic at the center of this story.

The four firms that litigated, Perkins Coie, WilmerHale, Jenner & Block, and Susman Godfrey, won complete legal victories. Permanent injunctions. Constitutional vindication. Their lawyers had successfully shown that the government cannot punish law firms for representing unpopular clients. That is not a small thing.

But consider their position relative to the nine settling firms. The injunctions protect against the specific orders as written. They do not stop the administration from issuing new orders with different language, investigating the firms through different regulatory channels, or targeting their clients through other means. The four firms that fought are free, but they are also at risk. They have no agreement with the administration. They bought no peace.

The nine settling firms bought something different: stability. As long as they meet their pro bono pledges and stay within whatever unspoken understanding they reached with the White House, they have, in effect, a guarantee against future targeting. They gave up control over a large portion of their pro bono practice. They bought protection not from courts, but from the administration itself.

Whether the litigating firms or the settling firms made the better institutional choice remains genuinely uncertain. The injunctions provide legal protection against the specific orders as written, set constitutional precedent, and have given the litigating firms a strong reputation in the legal community. Those are not trivial assets.

The settling firms, by contrast, bought implied political assurance. That assurance rests on unclear agreements whose enforceability is untested and whose terms were never made public. As Lawfare scholars noted, those agreements may be riskier than they appear. The litigating firms remain open to future executive action. The settling firms face future demands from the same party that pushed through the first round of concessions.

Marc Elias, a well-known voting rights lawyer, captured the practical meaning of this when Trump issued an April 2025 executive order. That order directed the Attorney General to create a mechanism for pro bono services to law enforcement officers defending their actions in civil rights litigation. Elias posted with dry humor: “Hey Paul Weiss associates — meet your new pro bono clients. It’s ok, the Skadden associates are getting the coal companies.” The point was not that defending law enforcement is inherently wrong. The point was that where those services went had been decided by administration pressure. It was not decided by the firms’ own judgment about where legal help was most needed.

Why the DOJ Dropped the Appeals Without Explanation

Rep. Jamie Raskin of Maryland, the top Democrat on the House Judiciary Committee, issued a statement titled “Ranking Member Raskin’s Statement on Court Victory for Law Firms That Refused to Capitulate to Trump” — framing the withdrawal as a victory for the rule of law — and he was describing something real. Courts had rejected the administration’s arguments. The constitutional principles had been vindicated.

But the withdrawal also helped the administration in a way that framing doesn’t capture.

By dropping the appeals without explanation, the DOJ avoided a formal ruling from the U.S. Court of Appeals for the D.C. Circuit. That matters greatly. The D.C. Circuit is one of the most consequential federal tribunals in the country. It is the court that handles most challenges to federal agency action and executive power.

A ruling finding this type of executive action unconstitutional would have set binding precedent across the federal judiciary. Such a ruling would have limited the White House’s ability to use similar tactics against universities, media organizations, nonprofits, or any other sector it might want to pressure.

By pulling back before that ruling could be issued, the administration avoided the risk of binding appellate precedent that could limit similar future action. The most likely explanation, given the timing, is that further litigation was both unnecessary and risky. The $940 million in redirected pro bono resources had already been secured. A ruling against them at the D.C. Circuit would have locked in constitutional limits across the entire federal judiciary. The withdrawal also fits a simpler reading: the administration’s lawyers decided their arguments were unlikely to hold on appeal, and preferred to cut losses rather than pile up adverse circuit-level rulings on the merits.

The administration has shown a steady willingness to force immediate behavioral change through executive pressure. It then pulls back before courts can set binding limits on that pressure. The coercion works on the timeline of business decisions. The litigation works on the timeline of federal courts. Those timelines do not match.

The Unconstitutional Conditions Question Nobody Has Answered

If the four litigated executive orders were unconstitutional, what about the nine settlements? This question has not been litigated. Legal scholars genuinely disagree on the answer.

The relevant doctrine is called “unconstitutional conditions.” It holds that the government cannot condition a benefit on waiving constitutional rights. Whether it applies identically to lifting punishments rather than granting benefits is less settled, but the core principle is the same: coerced agreement is not free choice. The classic example: a state cannot tie welfare benefits to a recipient’s willingness to give up free speech rights. The Supreme Court has recognized this principle in various forms for decades.

Applied here: the administration threatened economically devastating executive orders, then offered relief in exchange for pro bono pledges to government-approved causes. If the underlying orders were unconstitutional, as four courts found, then tying their withdrawal to the firms’ acceptance of those pledges might itself be constitutionally suspect. You cannot, in theory, use an unconstitutional threat to force a concession.

No court has ruled on this. The four litigating firms challenged the executive orders themselves, not the broader constitutionality of the settlements. The American Bar Association filed a separate lawsuit in June 2025 arguing that the executive orders and settlements together make up an unlawful “law firm intimidation policy” violating the First Amendment. That case remains pending.

Legal ethics scholars David Luban at Georgetown Law and Bruce Green at Fordham Law have raised related concerns in writing about lawyers’ ethical obligations. They argue that directing lawyers’ pro bono services to government-approved causes raises questions about whether those lawyers can stay independent enough to fully represent all clients regardless of political affiliation.

If a major firm is contractually committed to spending significant pro bono hours on Trump administration priorities, can that same firm’s lawyers strongly defend Trump opponents in private litigation without at least an appearance of compromise?

The settling firms have argued their commitments align with their core values. Paul Weiss managing partner Brad Karp stated the settlement would not require the firm to “compromise our core values and fundamental principles.”

The strongest version of the settling firms’ position is this: practical institutions facing unequal timelines made a reasonable choice. Suing the federal government is costly, slow, and uncertain in outcome. The harm to a firm’s lawyers, staff, and existing clients during a long fight is real. That harm falls on people who had no role in the underlying political dispute.

The pro bono commitments the firms accepted, veterans’ legal services, antisemitism task force work, and similar causes, may truly reflect values the firms hold regardless of how the conversation started. The services those commitments produce will be delivered to real clients with real legal needs, whatever the origin of the pledge. Firms routinely make strategic compromises to keep their ability to serve clients. This, the argument goes, was a large version of a familiar institutional calculation, not a surrender of principle.

That case has merit. But it does not resolve the constitutional concern, and here is why: the unconstitutional conditions doctrine applies even when the substance of the condition is harmless. The government cannot use an unconstitutional threat as a tool to force concessions, even concessions the recipient might have made freely under different circumstances. The coercive structure itself is what the doctrine forbids. A firm that would have freely chosen to fund veterans’ legal services stands in a different legal and institutional position than a firm that accepted that commitment to avoid being economically destroyed by the White House. That distinction, between a firm choosing its pro bono work freely and a firm choosing it under threat, is not one the firms’ public statements have been eager to address.

The Chilling Effect on Firms That Were Never Targeted

The thirteen named firms — four litigants and nine settlers — are the visible part of this story.

In July 2025, Reuters reported that major law firms, including some that had not settled, were substantially reducing their pro bono work, particularly work challenging government policies. After interviewing dozens of lawyers and reviewing major law firm websites alongside court records, Reuters found that “many firms are making a strategic calculation: withdraw from pro bono work frowned on by Trump, or risk becoming the next target.” Fourteen civil rights organizations told Reuters that firms they had relied on for pro bono representation were now hesitating to work with them. Some were keeping their representation secret or declining cases altogether.

This is the real policy outcome. Not the four court victories. Not even the $940 million. The goal was to change what the entire legal profession considers safe to do, and by that measure, the campaign has had clear success.

Judge Howell had identified this dynamic in her Perkins Coie ruling: the order was “intended to, and does in fact, impede the firm’s ability to effectively represent its clients.” The lasting harm was not just to Perkins Coie but to its clients and, through them, to the legal system’s ability to check executive overreach. Injunctions against four specific orders do not address that wider effect. If firms believe the administration can issue new orders or retaliate through other regulatory channels, the fact that courts struck down the first round of orders provides limited comfort. The balance of power has shifted.

The threat itself changes behavior, often before any court has a chance to review it.

The ABA Lawsuit and the Unanswered Constitutional Question

The American Bar Association’s lawsuit is the one remaining thread that could pull this whole episode into a formal legal reckoning. The ABA argues that the executive orders and the settlements together make up a systematic attack on attorney independence, violating the First Amendment not just in individual cases but as a coordinated policy. The administration has sought to dismiss the case.

If the ABA case gets past dismissal, it would push courts to face the question the four individual firm cases left unanswered: whether the settlement track itself is unconstitutional — specifically, whether pulling $940 million in redirected pro bono resources through the threat of unconstitutional executive orders violates the Constitution.

That is a much harder question than whether any individual order violated the First Amendment. It would require courts to look at the whole scheme of threats and settlements together, not just its individual parts.

Princeton sociologist Kim Lane Scheppele, who specializes in the sociology of law and has studied democratic erosion in Hungary, Poland, and other countries, has noted a pattern in this episode. She argues that pulling back after achieving coercive goals through executive action is a common feature of how governments operate in countries where courts are independent. They do not need to win in court because the threat itself changes behavior. Once behavior changes, the litigation becomes unnecessary. A 2025 Carnegie Endowment report analyzing the Trump administration’s approach concluded that “the administration is curtailing the basic forms of bottom-up political accountability that are fundamental to a democratic system,” meaning the ways ordinary citizens and institutions can hold government power in check.

That framing represents one scholarly perspective. Other legal scholars reach different conclusions. They point to the four permanent injunctions, the unanimous judicial rebukes, and the DOJ’s ultimate withdrawal as evidence that Article III courts worked exactly as the constitutional design intended. On that view, the courts checked executive overreach before it could become entrenched. The episode is then less a story of democratic backsliding than a stress test the system passed, though at real cost to the firms that took on the burden of litigating it.

The Scheppele comparison to Hungary and Poland, some scholars argue, is stretched too far — applied to a system whose independent courts blocked the challenged orders and whose institutional constraints stayed in place throughout.

The four firms that litigated proved that courts can stop unconstitutional executive orders. What remains unresolved is a harder question. Can courts stop an executive that uses unconstitutional threats as a bargaining tool, gets the concession it wants, and then walks away from the litigation before any binding ruling can limit its future options? That question is now sitting in federal court, waiting for an answer.

Our articles make government information more accessible. Please consult a qualified professional for financial, legal, or health advice specific to your circumstances.