Trump vs. Big Law

A former attorney explains why some firms are capitulating to the president while others are fighting back

Since February, Donald Trump has been issuing a series of executive orders targeting the biggest law firms in the country. In response, some firms — including Paul, Weiss; Kirkland and Ellis; and others — have capitulated to the president, striking deals to provide free legal services to his favored causes. Other firms decided to fight back, suing Trump over the orders in federal court.

Last week, former President Barack Obama was quoted criticizing the firms that struck deals with Trump — saying that top attorneys did so not because they were “going to get thrown in jail, but because they might lose a few clients and might not be able to finish their kitchen rehab at their Hamptons house.”

Attorney Matthew Wollin spent five years as a litigator at one of the Big Law firms targeted by Trump — WilmerHale — before he quit in March. He now writes about legal and other issues at his newly-formed Substack, as well as for numerous media outlets. We asked him to explain exactly what is going on.

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What exactly is in these executive orders?

Trump basically went after these firms’ ability to make money and operate effectively for their clients. Part of that involved attempting to revoke certain privileges. One of the things he did was attempt to take away security clearances for attorneys who work at these firms. Another was ordering reviews — and possible termination — of their government contracts.

Why did he target these firms specifically?

The real reason is that these firms are associated with Democrats or people who went after Trump in some way. So, for example, the one issued against WilmerHale — my former firm — was because Robert Mueller used to be a partner there.

The executive orders themselves give kind of a nonsense reason — mostly just name-calling, saying the firms are abusing the justice system. But it's very, very clear that he’s targeting them because they’re associated with people he personally does not like.

Big Law is just one of the institutions that Trump has gone after — along with universities, media outlets, and others. Why Big Law? What do Trump and the Republican Party have to gain?

Part of what makes this unique and important is that it’s a direct attack on the rule of law itself. It’s an attack on the system that allows opponents of the person in power to use the legal process to pursue their own ends. Going after these law firms is an attempt to use the power of government to limit the ability of political opponents to access the system that gives them a voice.

Why did some of these firms capitulate? And what did capitulation look like?

A bunch of these firms agreed to vaguely defined deals. Basically, they agreed to commit pro bono resources — meaning services for free — to causes Trump approves of. That presumably includes an implicit promise not to support causes he doesn’t approve of.

Why they did this, I can only speculate — although it’s so bewildering that I’m still trying to understand it. These agreements are incredibly vague. And if you know one thing as a lawyer, it’s not to agree to a vague deal. The bottom line is that they basically promised not to make Trump angry again.

My understanding is that Paul Weiss pledged $40 million in pro bono work to support the administration, and Skadden committed $100 million. That’s a pretty significant amount of money. And there is also a chilling effect, right? Any firm that is thinking about doing pro bono work on the other side is being told, you better not do it, or you might be next.

Yeah. It’s a message to any firm that's thinking about doing work on the other side — pro bono or not. A lot of these firms regularly represent clients who are adverse to the government in some way. It’s part of normal business. The intent here seems to be making sure these firms are less likely to take on causes in opposition to Trump.

One particularly interesting thing about the deals is that some firms capitulated preemptively. They reached out to Trump to make a deal, hoping to avoid being targeted by an executive order. So if you're looking for a chilling effect — it's already happening.

Now the head of Paul, Weiss — I'm going to give his defense. He said his firm was in danger of going out of business if it didn't cut a deal. What do you think of that?

I think that is, uh – not right. I'm trying to keep my language much nicer than I am inclined to. But I think that is basically lawyers trying to convince themselves that they know how to do business. Big law lawyers have a strange mindset, and it's a strange place to work. And I know this because I worked there for many years. There are incredibly smart people. They're great at their jobs and incredible intellectuals. But also it's a real echo chamber of narrow-minded thinking. Everybody went to law school, and everybody works exactly with people like them.

What happened when Paul, Weiss and some of these other firms started capitulating, it was a bunch of lawyers who don't have experience thinking through the long term PR and business consequences of their decisions. And them not having the ability to see the obvious truth that this is going to be not just a bad decision, but a very obviously stupid one that's going to lose them business. And that has been already happening in a very dramatic way.

People have been quitting very publicly. They are speaking out against these firms. They’ve lost some significant business. There has been a parade of consequences for the firms that have capitulated, which still continue to unfold — up to and including things like Barack Obama badmouthing them, which as a law firm is not something you're super excited to have happen.

On that point, is there a divide within the firms between the younger associates and the partners? I know your firm did not capitulate, but you know a lot of attorneys. I’m wondering what is going on inside these firms.

From the outside, these firms all seem very impressive, very monolithic. They're all called some string of last names that nobody can ever keep straight. They seem like a giant, homogeneous group of people. And one of the things that this has done is really blown open that myth. It has exposed that these are firms made of people who think different things.

As you're suggesting, we are seeing certain divides emerge within the firms. It has tended to be the younger associates quitting, probably because they have not lost their law school idealism and are sticking a little bit closer to their principles. But there have been some people at the upper echelons who have left as well, just perhaps not quite as vocally.

If you look at the timing of some of the partners leaving from these firms, they left in the immediate aftermath of all this. Even if they have not made public statements about the reason they are doing so, you can put two and two together. It certainly seems like the capitulation of some of these firms is making the lawyers within them at all levels rethink whether or not it is a place they want to be.

It feels like a really, really bad thing when the biggest, most powerful law firms in the country are essentially rolling over for any administration — Republican or Democrat.

It is. I cannot emphasize how much it is. And also how personally frustrating it is to me as someone who worked at one of these law firms. These firms are best situated to fight back against the administration of literally anyone.

I worked on cases that were not dissimilar from this. They weren’t against Trump, but they were constitutional, rights-based litigation about similar issues — and honestly, those were harder cases to win.

These firms know they could have won if they fought back. These executive orders are blatantly unconstitutional in a way that is very unusual to see. And so to have these giant, powerful law firms capable of winning this fight roll over without even trying to fight — that is pretty startling and frustrating and frightening for sure.

We've seen some firms, including your former firm, WilmerHale, that did fight back. Why did they fight back, and what did that look like?

First, let me caveat that this happened right after I left the firm, so I’m not speaking for them — just as someone who has experienced that world.

Fighting back here basically looks like bringing a lawsuit. After the executive orders were issued against them, they sued the Trump administration, asking the court to declare the order unconstitutional. And I imagine they did so because they knew they could win. And they also understood that it's not a great look for a law firm, whose business is predicated on effective representation, to immediately roll over the moment that somebody comes to fight you.

I think they probably saw that it was good business for them to fight — and also saw that by not fighting, they would be undercutting the value of what they do as lawyers in the first place. If you are going to help undermine the rule of law — which is the thing that enables big law lawyers to charge so much money — you would be helping to undermine the system that justifies your whole existence.

Have their lawsuits been successful?

They have. What is notable — and not surprising to me at all — is that every single firm that has fought back has been successful so far. They brought lawsuits at the lowest federal court level, and they've gotten courts to say that these executive orders are unconstitutional and thus don't apply to them.

It’s a striking statistic when 100% of the firms who fought back have been successful.

I want to ask about your decision to quit. You spent five years at a big law firm. I assume you were making quite good money. What was your frustration ultimately? Because these are jobs that a lot of people would kill to have.

I wish I could say it was related to the executive orders — it would make for a better story. But it was just an independent decision. I’d started publishing more legal journalism — like the kind we’re talking about now — and I wanted more time to do that.

These are amazing jobs in many ways. I worked on some really incredible litigation I was proud to be part of. I learned a ton. But they’re also intense work environments — you basically turn over your life to working 100% of the time. I didn’t want to do that anymore.

And as someone eager to make legal issues intelligible to a general audience — because lawyers are often terrible at speaking normal human language — I wanted the chance to try explaining things like this to people. I couldn’t have done that in the same way if I’d stayed at the firm.

Let's talk about the Supreme Court. Despite the rightward shift of the court, I think a lot of progressives still see it is the last, best hope to prevent some of the worst excesses of the Trump administration. Do you see it that way? Or is the court essentially just an extension of the administration at this point?

I think progressives need to stop thinking the Supreme Court is going to save them. That mindset is actively harming progressive causes — especially social ones. Every time a case involving trans or LGBTQ issues reaches the Court, you’re basically asking a bunch of ornery conservative uncles to rule on things that make them uncomfortable. That rarely ends well.

There’s a century or more of precedent of the Court making progressive, forward-thinking decisions — from Brown v. Board to Roe to early affirmative action rulings. For decades, the Supreme Court acted like the adults in the room. Progressives internalized that idea, so they keep bringing litigation to protect those rights. But it’s not working anymore.

In my view, progressives need to start looking elsewhere — to state courts, grassroots legislation, or other ways to advance their goals.

What gives you hope?

What’s been most encouraging is not just criticizing the Trump administration, but actively looking for examples of people building the kind of world I want to live in.

For example, one thing I wrote about last week on my Substack was that Rhode Island recently passed an anti-censorship law. I didn't even know that could happen — that there could be state legislative protections to help prohibit ideological censorship.

It is very easy to get overwhelmed in this news cycle, because Trump dominates it so completely. And it is very worth it to seek out things that help you envision a better world — and not just live in this kind of chaos reaction, fear-based news cycle.

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