Constitutional Showdown as Law Firms Respond to Executive Orders Targeting Their Clients, Hiring Practices, and Pro Bono Work
In an unprecedented campaign against the legal profession, President Donald Trump has launched a sweeping offensive against major U.S. law firms, issuing executive orders punishing those he perceives as politically or ideologically opposed to his administration. The orders target firms for their clients, pro bono work, and diversity-based hiring—raising profound constitutional questions about the separation of powers, First Amendment rights, and the rule of law.
While some firms like WilmerHale, Jenner & Block, and Perkins Coie have chosen to fight the orders in court, others, including Skadden, Arps, Slate, Meagher & Flom LLP and now Milbank LLP, have opted for strategic settlements worth hundreds of millions in free legal work and policy concessions.
Milbank Becomes Fourth Major Firm to Cut a Deal
On Wednesday, Milbank LLP became the fourth major law firm to cut a deal with the Trump administration. The firm agreed to provide $100 million in free legal services for initiatives mutually approved by the White House. The firm also agreed to abandon diversity-based hiring, aligning with Trump’s pushback against DEI (diversity, equity, and inclusion) programs in the legal industry.
Milbank’s deal mirrors previous arrangements struck by firms under pressure from the White House, and underscores the deepening rift within the legal profession over how to respond to the president’s increasingly aggressive tactics.
In a letter to Milbank employees, Chairman Scott Edelman acknowledged the firm had been approached by the administration with concerns about its pro bono and diversity efforts. While the letter doesn’t confirm that an executive order was imminent, Edelman wrote that the agreement would help the firm “put these issues behind us.”
“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 said. “With this agreement, we believe we have gone a long way to putting these issues behind us.”
Edelman had previously signed a 2021 letter urging Congress to certify President Joe Biden’s election victory, placing him on the radar of Trump’s political allies.
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Split Reactions: Some Firms Sue, Others Settle
The legal industry now finds itself at a crossroads: whether to challenge executive power in the courts or negotiate settlements to preserve access to federal contracts, buildings, and classified work.
So far:
- Three firms—WilmerHale, Jenner & Block, and Perkins Coie—have filed constitutional challenges.
- Four firms—Skadden, Paul Weiss, Milbank, and Willkie Farr & Gallagher—have reached deals.
- Covington & Burling has been targeted by a limited order but has not sued or settled.
In its lawsuit, Perkins Coie argued that the executive order poses a fundamental threat to the legal profession. In a recent court filing, the firm warned that if allowed to stand, the order would “set a grave precedent” by enabling the president to punish lawyers for their choice of clients. The Trump administration dismissed the concerns as “pure conjecture and speculation.”
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Trump’s Expanding List of Targeted Law Firms
President Trump has now issued executive orders targeting five law firms, and pressured several more into preemptive settlements. His stated justification: punishing firms for their role in what he calls the “weaponization of the legal system” against him.
Targeted Firms and Responses
| Law Firm | Executive Order? | Response | Reason for Targeting |
|---|---|---|---|
| WilmerHale | ✅ Yes | Sued Trump, injunction granted | Hired Robert Mueller |
| Jenner & Block | ✅ Yes | Sued Trump, injunction granted | Ties to Andrew Weissmann |
| Perkins Coie | ✅ Yes | Sued Trump, injunction pending | Hired Marc Elias, Clinton ties |
| Paul Weiss | ✅ Yes | Settled: $40M pro bono + DEI review | DEI policies, client ties |
| Skadden | ⚠️ Avoided via deal | Settled: $100M pro bono | Promised legal services |
| Milbank | ⚠️ Avoided via deal | Settled: $100M pro bono + DEI retreat | DEI, Trump critic partner |
| Willkie Farr | ⚠️ Avoided via deal | Settled: undisclosed terms | Partner Doug Emhoff |
| Covington & Burling | ✅ Yes (limited) | No lawsuit or settlement yet | Advised Special Counsel |
Legal Firepower on Both Sides
To take on the executive branch, firms have brought in some of the legal world’s biggest names:
- WilmerHale hired Paul Clement, former Solicitor General and leading Supreme Court advocate.
- Jenner & Block retained Michael Attanasio of Cooley, a former federal prosecutor.
- Perkins Coie continues to be represented by internal counsel and constitutional law experts.
Trump, for his part, is backed by allies including Elon Musk, who has publicly attacked law firms like Cooley and Perkins Coie as “white-shoe lawyers” who “thrive on corruption.”
Judicial Developments and Broader Implications
The lawsuits have already prompted judicial intervention. Two federal judges temporarily blocked key portions of the executive orders against WilmerHale and Jenner. One judge said it was “disturbing” that Jenner appeared to be punished for representing transgender people and immigrants. Another warned that the WilmerHale order could cause “severe” spillover effects in the justice system.
These rulings signal serious judicial concern about Trump’s use of executive authority to retaliate against law firms—and suggest that the courts may not ultimately uphold these orders as constitutional.
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Conclusion: The Legal Profession at a Crossroads
Trump’s campaign against Big Law has fractured the industry. Some firms are taking principled stands, suing to uphold constitutional rights and preserve legal independence. Others are choosing the path of least resistance, cutting deals to avoid costly litigation and protect their government-related work.
Either way, the implications of these orders and settlements are likely to reverberate far beyond the courtroom. They could shape the future of legal ethics, executive power, and the attorney-client relationship for decades to come.
