By Chuck Gallagher — Business Ethics Keynote Speaker and Trainer
TL;DR: Chuck Gallagher, business ethics keynote speaker, examines why the nine Big Law firms that pledged $940 million in free legal work to avoid Trump executive orders are now facing Justice Department subpoenas — and what their calculation reveals about how smart people rationalize choices made under pressure.
Picture the room. Late March, 2025. A managing partner on a high floor in Manhattan is staring at an executive order with his firm’s name printed on it. Security clearances revoked. His lawyers barred from federal buildings. His clients with government contracts told they’d have to disclose the relationship. Perkins Coie, one of the first firms hit, told a court it began losing business within hours. The judge who halted the order against WilmerHale wrote that the firm’s survival was at stake.
Now sit in that chair. A thousand partners. Families depending on the distribution. And a man on the phone who says this can all go away.
Nine firms took the call.
What Did the Firms Actually Agree To?
In late March 2025, nine of the country’s largest firms pledged a combined $940 million in free legal work toward causes the administration favored. Paul Weiss went first at $40 million. Kirkland & Ellis, Latham & Watkins, Simpson Thacher and A&O Shearman each committed $125 million. Milbank, Skadden, Cadwalader and Willkie Farr each put up $100 million. Nobody admitted wrongdoing. Several later told Congress the agreements were legal and ethical. Simpson Thacher called the suggestion of a violation wholly without merit.
Here’s what that money bought. Nothing.
On July 14, the New York Times reported that the Justice Department has subpoenaed all nine firms, seeking depositions from their leaders and communications with Boris Epshteyn, the president’s personal lawyer who brokered the deals. Bloomberg Law reported the firms were caught off guard and have hired outside counsel. Caught off guard. Lawyers, hiring lawyers. Walter Olson of the Cato Institute put it plainly: settling with this president does not buy you legal peace, and it does not buy you certainty about what you owe.
That’s counterparty risk. Every deal lawyer in those buildings could define it in his sleep. Who am I actually dealing with, and what happens if they don’t hold up their end? They knew the term. Not one applied it to himself.
Was the Deal Ever Really a Deal?
Consider what wasn’t in these agreements. No deadlines. No enforcement mechanism. Bloomberg Law reported some were never signed. The Wall Street Journal said the terms were essentially written on a digital napkin. Nine of the finest contract shops on earth made the most consequential agreement of their institutional lives without paper worth the name.
As a business ethics keynote speaker, I have spent two decades asking people one question: what were you thinking when you made that choice? Nobody says they woke up that morning wanting to do wrong. Almost nobody, anyway. What they describe is three things lining up — need, opportunity, and rationalization.
The need was survival. Revenue. Partners threatening to walk with their books of business.
The opportunity was the offer itself, a door swinging open while the room was on fire.
And the rationalization was the prettiest part. It’s pro bono. We do pro bono anyway. Where’s the harm in pointing some of it at causes the White House likes? It’s citizenship. No harm, no foul, so to speak. Now, the way I see it, rationalization is the most dangerous of the three. It’s the one that lets a smart person sleep. And these were very smart people.
What Happened to the Firms That Said No?
Four firms got hit and fought back: Perkins Coie, WilmerHale, Jenner & Block, and Susman Godfrey. All four won. Every order against them was struck down in federal court as unconstitutional, and few expect them overturned on appeal.
Read that again. The firms that took the deal are now hiring defense counsel. The firms that refused are practicing law.
I don’t say that to be smug. Nobody in that March room knew how the rulings would come out. That’s the entire point — real ethical choices get made in the fog, before you can see the consequence. But here’s a pattern I’ve watched in courtrooms and boardrooms both. The party who folds fastest, hoping to make it stop, often lands in the worst spot. Cooperation isn’t the problem. Fear is what drives a fast decision, and fear skips the questions you’d ask on any ordinary Tuesday. Trust me.
Is Any of This Ethical?
Fair question. The answer depends on where you’re standing. The administration argues in court that a president gets to decide whom he trusts, and that his deliberations are shielded by presidential communications privilege. The firms told Congress they voluntarily agreed to donate legal work and broke no law. Voluntarily. The American Bar Association argues the orders were part of a deliberate policy to discourage lawyers from taking positions against the president. Here’s the uncomfortable wrinkle: the Justice Department has itself pointed to the nine settling firms as evidence the policy worked as designed.
Set the politics down a minute. I’m not interested in which team wins. I’m interested in what happens when the people whose job it is to check power start pricing out whether it’s worth the cost. A lawyer’s duty runs to the client. That isn’t a nice sentiment somebody stitched on a pillow in the reception area. It’s the floor the whole structure sits on. When a firm asks whether taking a client will cost it, rather than whether the client has a case, the floor moves. ProPublica reported that Big Law began backing away from certain clients almost the minute the administration returned to power. No order required. The possibility of one did the work.
The subpoenas will make the headlines. The chill is the actual consequence.
What Should a Leader Take From This?
As a business ethics keynote speaker, I get asked constantly for the rule that prevents this. There isn’t one. We want to believe that a code of conduct, signed at orientation and filed away, will stop a person who has already talked himself into something. It doesn’t. Not even close. What works is a question, asked out loud, before the choice: if this gets read back under oath in three years, does it still look right?
Nine firms didn’t ask it. Their leaders may answer it under oath anyway.
Every choice has a consequence. You don’t get to pick the consequence. You only get to pick the choice.
Frequently Asked Questions
Why did nine law firms make deals with the Trump administration?
Fear, mostly. Beginning in March 2025, the Trump administration issued executive orders against several major law firms that revoked security clearances, barred attorneys from federal buildings, and threatened clients holding government contracts. Perkins Coie told a court it started losing business within hours of being targeted. Hours. Nine other firms reached settlements with the White House to avoid orders of their own, pledging a combined $940 million in free legal services toward administration-favored causes.
How much did each firm pledge in the Big Law Trump deals?
The nine committed $940 million collectively. Paul Weiss pledged $40 million; Milbank, Skadden, Cadwalader and Willkie Farr pledged $100 million each; and Kirkland & Ellis, A&O Shearman, Latham & Watkins and Simpson Thacher & Bartlett pledged $125 million each. Reporting has noted the agreements contained no deadlines and no enforcement mechanism, and that some were never signed. A $940 million handshake.
Are the Big Law settlements with the Trump administration legal?
The firms say yes, and so far no court has said otherwise. In May 2025 letters to Congress, most of the nine defended the agreements as legal and ethical, with Simpson Thacher calling allegations of violations wholly without merit. Congressional Democrats have questioned whether the deals amounted to improper inducements. No court has ruled on the settlements themselves. The executive orders that prompted them, however, have been struck down as unconstitutional in every case litigated so far.
What happened to the law firms that refused to settle with Trump?
All four that fought won. Perkins Coie, WilmerHale, Jenner & Block, and Susman Godfrey each challenged their executive orders in federal court, and judges found the orders unconstitutional. Those rulings are on appeal, but few observers expect them to be overturned. I’ve made the point on stage more than once since: the firms that fought are practicing law today, and the firms that folded are answering subpoenas.
What is counterparty risk and why does it matter here?
Counterparty risk is the possibility that the other side of an agreement won’t honor its end. Every one of these firms prices it for clients constantly. Then the July 2026 subpoenas landed. They had treated a handshake with a counterparty holding enforcement power as though it were a binding release, with no deadlines, no enforcement mechanism, and no paper worth the name. They knew the term.
Continue the Conversation
Most organizations will never face an executive order. Every organization will face the moment those nine firms faced: pressure on one side, a shortcut on the other, and a rationalization sitting right there waiting to be picked up. The firms that handled it best weren’t braver than the rest. Bravery had nothing to do with it. They had simply decided, in advance, what they would and wouldn’t trade. That decision gets made in calm rooms. I bring audiences inside the need-opportunity-rationalization pattern that drives these choices — drawn from the boardroom, the courtroom, and my own consequences. If you want this conversation in front of your leadership team, association, or firm, visit ChuckGallagher.com.
Five Questions for Reflection
1. The nine firms had the offer on the table and the fire in the room at the same moment. Where in your organization does urgency currently outrun scrutiny?
2. Each settling firm publicly maintained the deal was legal and ethical. What’s the difference between the two, and which one are your people actually being measured against?
3. Counterparty risk is something these firms price for clients every day. What risk do you assess for others that you have never once assessed for yourself?
4. The four firms that refused had no way of knowing they’d win. What would you have to believe about your organization to say no before you knew the outcome?
5. If a choice you’re weighing this quarter were read back to you under oath in three years, does it still look like the right call?
