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This episode is brought to you by Progressive Insurance. Do you ever think about switching insurance companies to see if you could save some cash? Progressive makes it easy to see if you could save when you bundle your home and auto policies. Try it@progressive.com Progressive Casualty Insurance Company and affiliates. Potential savings will vary. Not available in all states. Welcome back to the Tara Palmieri Show. You know something big is happening when lawyers start walking away from million dollar salaries to defend the rule of law. My guest today, Matthew Wallen, was an attorney at William Hale. It is one of the most prestigious law firms in the country. You might recognize its glass walled offices from the HBO show succession. So he saw up close how President Trump's attack on the entire legal industry affected his firm before he left to become a journalist. We talk about why so many law firms caved settling with Trump before he even came after them. And what it says about the state of American institutions when even the lawyers who are supposed to be the defenders of democracy and the rule of law are settling with the very man challenging it. We also dive into the quiet rebellion among young associates and law students refusing to work for firms that capitulated. And how a handful of new rule of law startups emerging in their place. A silver lining, you could say. Matthew wrote about all of this in the New Republic in a piece called the Lawyers who Gave Up Big Money to Fight Trump. It's a story that raises a bigger question, though. If the people who are supposed to uphold the law are folding, who's left to fight? And it's not just happening in law. We're seeing it across the board in media, tech, finance and academia. So let's get into it. My conversation with Matthew Wallen. Matthew, thank you for joining the show. First of all, I want to ask you, what made you decide to come to the dark side of journalism? Leave Big Law yourself. How do we manage to get you over here?
B
Yeah, for sure. I mean, is journalism the dark side? If it is, I'm still finding out, I guess. But so far, no, no.
A
I mean, we would say in, in journalism, PR is the dark side, but not everybody tends to want to go into the journalism business as it's not quite as lucrative as Big Law. So that's why I'm curious.
B
It's true. I mean, I think Big Law was great. I worked, my job was great. I learned a ton. I worked on a lot of amazing things. But I also, I mean, I, I feel like I'm a writer fundamentally and I like writing to large audiences. You know, like, I find it more interesting to communicate with non experts, basically, to kind of take what I know and help share it with the world. And I felt like there was both a need and like a. A place for that in the world these days, particularly with law stuff. You know, there's like, legal stuff is very important nowadays. It's very, like, in the news, obviously, but lawyers are by and large pretty terrible at explaining it and talking to normal people and sounding interesting and doing all of those things, because lawyers love their legalese and they're darkened and stuff like that. And so I kind of thought there was a place for me there in part because my career has been very all over the place. I'm pretty good at translating between worlds. And so I kind of started to publish some stuff. It was going well, and then decided to take the jump.
A
Yeah. Wow. Good for you. And what law firm were you working at?
B
Wilmer Hill. Okay.
A
Wow, that's a big one.
B
It is, yeah, it is. Yeah. It's one of the big law. Or it's one of the. What's called big law firms. I'm sure we'll get into this more, but it's one of the set of the biggest and kind of most prestigious law firms. There's a big office in New York. The claim to fame for the office is that it was literally the set for succession. So if you're getting a sense of what the vibe was like at the office, at least visually, it's that all glass boardroom sort of look.
A
And how many years did you work there?
B
About five years.
A
And what college did you go to or law school?
B
I went to NYU Law School.
A
Yeah. That's a really good one.
B
Yeah. I mean, NYU Law is a really good school. Wilmary Hill, it's a very intimidating place to work. You know, everybody is incredibly smart. Half my bosses had clerked for Supreme Court justices and like, other similarly impressive stuff. And it's one of those environments where being good is just kind of like normal, you know?
A
Yeah.
B
You almost start. You almost start to. Or I, at least just out of, like, selfishness, almost started to hope to encounter someone. Like you keep waiting to encounter someone who's not good at the job so you can just be better than them. And that never happens because somebody is good at their job.
A
Right. A lot of type A people, I'm sure.
B
Very much so, yes.
A
Right. So everything sort of changed, though, in February 2025, when Trump put out this initial memo targeting Covington and Burling. How did this set off a chain of events inside of the industry. Were you still working there?
B
I was, I was still working there until March it started. I mean, it was kind of shocking. I mean, both shocking and not shocking knowing Trump, you know, but it was shocking because normally lawyers are kind of off limits even in like the worst political battles. You know, I think in a lot of ways lawyers are seen as, and see themselves as kind of neutral people basically who will represent either side. You know, like they, they kind of hold access to the law, but they are usually not the targets. And so when Trump went after the lawyers themselves, the law firms, it was just from my standpoint as like a lawyer and someone who learns in law school, you know, what the law supposed to represent. It was kind of shocking. And it was like, who's going to be next? And certainly I worked at Wilmer Hill, which, again, great place to work. It is like pretty widely known as like a very progressive, generally Democratic leaning firm. And so it certainly felt like it was only a matter of time before his gaze moved towards where I was working. And so there was definitely an increased awareness of that, that being on the horizon. For sure.
A
There is this sort of paradox though, like you said that you did work for a progressive Democratic firm, but yet the law is seen as not political. You know, I remember when I was a kid, my mom worked, worked at Cory Booker's law firm and it was very much a, felt like a, I mean, what she was doing wasn't political work. But it, law tends to be political, so it's, it's hard to sort of divorce the two. Not to say that that should be a reason to be targeted, but it's hard to play the game of like neutral arbiter when so many of the law firms do see, do seem to have one. You know, like Jones Day is very conservative and you see various people that work from the Trump administration coming from there. So how do you sort of make the argument that there are neutral arbiters while working at these law firms that tend to take on cases that reflect their own views?
B
Yeah, I mean, you cut to the heart of the issue, like almost immediately right there. Particularly the heart of the issue when it comes to big law firms in particular, in that they are this kind of paradox of a modern workplace where there is this kind of democratic lawyerly ideal that all lawyers learn in law school, you know, where, where like, they're integral to the proper functioning of American democracy, they ensure the court systems work. Right. The kind of adversarial in courts back and forth is how the truth comes out. It's how justice is served. And then there is the reality of like being a modern day lawyer, particularly at a big law firm where you are often working on behalf of like the highest paying clients. And often a lot of these firms too do have kind of like idea, ideological leanings in one direction or the, and devote their free time towards doing a particular kind of work. I think when it comes to that latter part, when it comes to like Jones Day leaning conservative, for instance, or Willmah leaning kind of Democratic, a lot of that is seen by the people who work there as kind of like a side thing, almost like a little outside the normal like day to day business of being a lawyer, which is much more like a company comes in and hires you to sue this case or defend them or help them with a merger or do whatever. And all that I think is regarded as pretty neutral. And it's kind of like on the, on the fringes with pro bono stuff, with other things where the firms kind of provide a venue for the lawyers who work there to invest time in things that they care about.
A
So that's when it usually gets political.
B
Yeah, I mean it's hard to, it's like hard to generalize too much, but yeah, it's not, it tends to not be in the day to day stuff. You know, like the day to day stuff is a lot more corporate law, you know, by and large big companies.
A
Because that's what you make money on.
B
Really. Yeah, for sure. And so, so most of the firm's day to day business in my experience is taken up with stuff like that. My, my personal experience was a little unusual just because I, what I focused on at Wilmar was largely they have an anti discrimination practice. And so I worked on a lot of like rights based and constitutional law stuff. But that is not, that's a little unusual, by and large. It is like corporate stuff that takes up people's time at big law firms.
A
Hmm, interesting. So one thing that I found to be really surprising, when President Trump, you know, made it known that he was going to go after the big law firms. Right. Many of them reached out to him first to settle. And I kind of think it's one of the worst stereotypes about lawyers that they often settle first. And Trump himself said he was surprised by his own success that law firms agreed to make deals with him on such shaky grounds. That says something, doesn't it?
B
Yeah, I mean if, if, as I said to someone else, if Trump is surprised at his own success, you know, that it's like it was really must have Been weak ground because he is not a man who tends to be surprised at his own success. And so, yeah, it was really, really shocking, particularly because these law firms are just to, like, take a step back. The executive orders that he issued, targeting them, from my standpoint, were just, like, terribly weak orders from. From a constitutional standpoint. So, like, these are cases that the law firms that if they. If they fought, the ones that did choose to fight, they won. Like, it was not a close case, you know, and so it was particularly shocking to see these lawyers, who were kind of supposed to be the biggest, fanciest lawyers in the world, capitulate on something that they almost certainly could have won. And it's just weird because it really felt to me just like even stepping it back from the kind of politics of it, it felt like shooting yourself in the foot as a professional, you know, to be like, if you make your money being like, we are the best fighters in the world, we are the best at representing our clients, to then roll over on an easy fight, the moment that, you know, it comes to you, it feels a little bit shocking just as like, a professional. From a professional standpoint.
A
Yeah, but they do this a lot, though, lawyers. They. They tend to lean towards settling.
B
What are you thinking of in particular?
A
I don't know. It's just in my. Like, I Just. From the stories that I've covered and my experience, like, I feel like the first people are more likely to just come to the table and say, okay. I mean, maybe I'm thinking of sexual harassment cases.
B
Okay.
A
In particular.
B
Yeah. Yeah. I mean, that's interesting. That's a very different context, I think. I mean, I think you. You are absolutely right. And I'm trying. What I'm trying to do is reconcile this with the stereotype of my head that lawyers will sue at the drop of a hat, which is also true to some extent, you know, and so I think lawyers. I mean, lawyers are a complicated beast. They tend to be very litigious, but they also tend to use, like, litigation as a route to settlement, basically. So, you know, like, whereas I think non lawyers tend to think of suing as, like, always ending up in front of a jury, where someone says who's right and who's wrong. With lawyers, it tends to be a little bit more of a negotiation tactic.
A
Right.
B
And so I think that might be what's happening here, where these firms or some lawyers, like, they just decided to try and cut out the middleman as opposed to, like, fighting this and doing litigation that got halfway and then settling Perhaps these terms were just like, you know, we're going to jump to the end point because we know how most litigation ends, we know that it settles. And so we're just going to settle with Trump right off the bat.
A
Right. You also have to think to yourself that they may be preoccupied with their shareholders or thinking about the fact that insurance companies might not be willing to carry them for very long. Right.
B
I mean, I think they are definitely preoccupied with their profits, for sure. Law firms don't have shareholders generally, they're partnerships. So it's not set up quite the same way. But the principle of what you're saying is correct in that these firms were absolutely concerned with their business, they were concerned with their profits. And it was really a moment where it was. You could see lawyers in real time choosing to prioritize business interests over legal interests from. And, and that was what made it so interesting to me because it's this kind of conflict that you already alluded to that normally kind of goes along below the surface of the day to day lawyering. But this really brought it into the open and suddenly these lawyers took a stand. And what they took a stand on was not the thing that lawyers are supposed to like. You know, they went the other way. They went towards business interest, they went towards kind of like protecting their income streams for the most part. And that was striking.
A
And that's not unlike the media and what we've seen in their settlements with President Trump. Cbs, abc.
B
Yeah, it's fascinating. I also, I also think it's fascinating in terms of what the universities are doing too, though. It's obviously not like taken exactly the same route. But yeah, I think it's very possible. There was actually just a piece about this in the New Yorker like a couple days ago that what the big law firms did by capitulating was kind of set a standard, like a really unhelpful standard for other industries basically to, you know, also roll over a little bit when this fight came to them. And because lawyers are supposed to be the standard bearer when it comes to fighting legal fights, basically that's what they do. That it almost certainly had a kind of example setting effect.
A
What do these deals look like that they're making?
B
That's a great question. And nobody really knows. I mean, really. Yeah, I know. It's part of what's so fascinating is that so for instance, the. They made these deals, they're incredibly vague. They generally involve a commitment to contribute a ton of pro bono, meaning free services from the firm to kind of favor trousers Causes of Trump, like what? But for. It's very vague, which is part of the problem. So, like, the. Some of the firms claim that it was just stuff they would have done anyway, but Trump was clearly did not see it that way and was like, no, they're going to help me negotiate trade deals. They're going to help me defend police officers accused of misconduct. A lot of kind of like PR dicey stuff that I imagine these firms would not want to get into. And just as an example of how incredibly ambiguous these are when. So there was a bit of. There was congressional inquiry where they asked the firms to send them the contents of the deals, basically because Congress was worried that it might be unconstitutional. And the firms responded in incredibly weird and unhelpful ways, like quite literally telling Congress to go look at Trump's tweet, you know, for the full contents of the deal, which is not.
A
And what did it say again?
B
I. I don't remember exactly, but it was basically, you know, it was a classic Trump media post where it was kind of like, exactly. Yeah, yeah, it wasn't. It was definitely not what you think of as a legal deal. And another one said Congress should go look at an internal email that had been reposted in an industry trade magazine that was behind a paywall. So. So clearly the firms were not. They didn't have a piece of paper somewhere that was like, here is exactly what we agreed to. And again, from the standpoint of being a lawyer, that's pretty bad lawyering, to agree to something when you don't know what you're agreeing.
A
Yeah, I was going to say, what lawyer would sign off on a document like that?
B
Yeah, if you know anything about lawyers, even more than they don't care about.
A
The fine print when it comes to the President, I mean, they're completely held.
B
Hostage, absolutely everything in writing. And for that not to be done here was just, like, really shocking from a professional standpoint.
A
Wow. Do you think this is a betrayal of legal ethics?
B
I do, for sure. Yeah. I think. I mean, lawyers have a. I think it's a betrayal of their job in several ways. Like, in the legal ethics standpoint, for sure. I like. Lawyers are supposed to uphold the rule of law in the country. And like, these attacks were a very direct attack on the rule of law, but arguably the most direct attack on the rule of law to date. And to kind of like roll over and capitulate that to that without even a fight is a pretty big betrayal of what lawyers are supposed to stand for. I also think it's a pretty big betrayal of like lawyers being good at their job and what they're like, the function they're supposed to serve, even to their clients. Where we were talking before, how if you, you're supposed to be an effective advocate for your clients to like roll over in this way is, is I think kind of a betrayal of what lawyers are even supposed to be doing in a day to day sense.
A
Yeah, I'm sure it's a conflict of interest for the rest of their clients too. I mean, do they no longer represent people who are being targeted by Trump now?
B
So, I mean, it's a great question. In, in general, there's been stuff written about and it seems like this, these attacks and the capitulation have had an effect similar to that where it's harder to get representation if you're fighting against Trump. There's been some notable counterexamples. For instance, I mean, like, and this is the piece that I wrote a little while ago, there's been some notable counterexamples of small new firms and new things starting up explicitly to take up this fight that the big law firms would not. And so there's definitely like, representation is not gone. But of course, like seeing big law firms capitulate in this way to the President has had a chilling effect on anybody else who was trying to get representation for, you know, against the President.
A
I mean, you need like the fire brands like Abby Lowell who have already made their bones, right? He's created his own firm. And just for context, Abby Lowell has really represented every major case in the past, you know, modern political history, you know, at least since I've been alive. I remember covering him in the John Edwards trial. John Edwards was acquitted. He covered, he worked for Josh Jared Kushner and then went on to work for Hunter Biden. He's everywhere. And now he is representing Tish James. He's left his law firm to be able to do that. But that's a, I think that's a pretty stark example of a prominent lawyer leaving to create his own firm to take on the Trump administration. I know you wrote about some associates that left and, and, and, and law students who have boycotted in a way. They've said that, you know, they're going to withhold their talents from these big law firms that are trying to recruit them. Has that been successful?
B
We'll find out. That's not going to be an overnight thing. The recruiting thing specifically happens on a very rigorous year to year schedule. And so this will be something where we see the effects on these firms in years to come, basically, I think in terms of the reputation, it's already had an effect. As someone who went to law school and went through this process, reputation among these firms is kind of everything law students view these firms as. It's the start to your career. It's like, like getting into one of these firms is like a golden ticket sort of situation because it just sets you up in so many ways. And so you don't want to screw that up, you know, you don't want to, like, choose a firm whose reputation is going to work against you in the long run, for sure. And so I suspect it is. I suspect it is like sending more students away from the firms that capitulated. But it's going to be a, like, it'll be one of those things that'll be really interesting to track in the coming years, how these firms evolve, because I think this has changed their trajectory in some ways.
A
And let's just talk a little bit about what they're resisting or giving up at one of these big law firms. $250,000 a year starting salary, and I.
B
Think that's the latest.
A
Yeah, yeah. And you could go up to making as much as 6 million or more. Right. And that's hard to say no to when you're leaving law school with up to $130,000 in debt, right?
B
Oh, for sure. It's wild. I mean, there is like, part of what makes these law firms, these big law firms, such a. Like, a crucible for all these difficult forces is that there's so much. It's so desirable to go there, and there's so much pressure to go there in some ways, particularly going to law school, which is famously very expensive and like, often leaves people with a lot of debt. When you're graduating that debt, it's hard to say no to an opportunity that promises to pay it off pretty quickly. And particularly when you're looking at an opportunity like big law, as compared to if you wanted to go do something kind of purely, I don't know, like, purely public interest oriented, that was kind of less morally complicated. Those jobs pay drastically, drastically less. And so, like, yeah, it takes a real conscious effort to turn away from this kind of opportunity.
A
Yeah, no, it, it does. And that's why I wonder if it's real. I wonder if they'll really be able to do it.
B
Yeah, it's a good question. I mean, I think. I think there is serious doubt that it'll lasts, that this kind of, like, new resistance movement will last so to speak. But I also think that's one of the reasons that it's worth talking about, because I think sometimes with movements like this or things happening, like talking about, it's like a matter of perception, if people perceive it to be a real thing, as opposed to kind of just like being a flash in the pan.
A
Right.
B
Which is why I think it's like a story that is like, like dig deep in reach and is worth. Exactly. Because I think like, leaving it unexplored ensures that it won't happen.
A
It really depends on how the economy is as well and what kind of opportunities they have.
B
Yeah, for sure. And I, I don't know. I am not an economist and who the heck knows what's going to happen currently with the economy in the next few years?
A
But don't read 1929, otherwise you put all your money in your underwear. Draw Doug Emhoff, by the way, First Gentleman, is still working for Wilkie Farr, a. A major law firm that obviously settled with Trump. And there was a mass exodus at the firm, but it did not include Emhoff, who, you know, is essentially working at a firm that's helping a man who may run again in 2028 when his wife wants to run, or as at least they both have hinted at the possibility that they both could run. And, you know, it's said some pretty horrible things about her and the party that she represents.
B
Yeah, I mean, I think it just goes to show how complicated these big law firms are. You know, like, there is. There was definitely an exodus of some people, but those people were the outliers. Like the vast majority of people who worked at these places kept working there. And I think it's because to leave is like a huge personal and professional risk. You know, it means putting your name out there into the public as someone who's willing to quit because of what you believe in, which is generally not a super hireable quality from, you know, most companies and places. Yeah. It means giving up a lot of money.
A
Yeah. And then they're like, oh, you're dramatic. You're not going to go along with things. Right.
B
Exactly. And although it's for the right reasons, like, you know, I mean, just like real world, it's hard to get rid of that kind of like mark on you. It just means taking a lot of risk, particularly early in your career. I feel like there's a risk too, for partners later in the career, but at least from my standpoint, it feels like they have some more power in this situation. But also, I would imagine you know, people who are lawyer partners at big law firms are realists for the most part. I would be like a little bit surprised to like encounter a ton of really naive, pure hearted idealists. And so it doesn't shock me that a lot of the partners stayed because they're just, I don't know.
A
And they have their lives now and their homes and their kids go to private schools and they spend time with the, they spend time with people who work in the administration and this is their, these are their lives.
B
Living in and, and disrupting your life that majorly is, is a big thing. And I get it. And like, I, I, I don't mean to judge them too harshly for it because I get leaving my law firm, which I did not do in protest. I, I liked working there a lot. But even like quitting a normal job for normal reasons also already a big disruption to your life and.
A
Because I'm a journalist.
B
Yeah, I know.
A
When I told my parents I was going to be a journalist, they were like, you are going to be a waitress for the rest of your life. Just so you know.
B
Yeah. I mean it, Yeah, I mean, but, but parental approval is a tricky thing always, no matter what you do. I feel right.
A
It would have been much happier if I went to law school, I'm sure.
B
Yeah, well, imagine how my parents were when I left the law job to go do other things. For sure. Yeah, that's true. But yeah, I mean, so leaving your job in the best of times is a difficult thing. Leaving your job under pressure, having to make a decision like that and like tell everyone you know and not just tell everyone you know, but tell the whole world that this is what you believe and what you stand in. It's a big deal, you know, and.
A
You don't really see the max mass exoduses out of media companies either. Really. And you're not really seeing them out of academia. It's very rare. People are getting jobs.
B
It's true. The, the, the lawyers. Right. That's a really good point actually. And I haven't thought about that. It's interesting because when I think of media training, I don't know, I am not a, I'm not a journalist, but I am a journalist. But what I mean is like I didn't go to journalism school, so I.
A
Was not, it doesn't matter. You don't learn anything there anyway.
B
Okay.
A
Trust me, I would have been better off studying anything but communications.
B
Well, I'm glad to know that I didn't. Good. That I made the right decision there but my point is that lawyers do have this particular worldview, particularly in their education where you're trained, that, like, not just in how to do your job, but, like, there is a moral aspect to your profession.
A
Right.
B
Like, like, we have that too, though.
A
We have moral codes. Yeah, keep going though.
B
Yeah, yeah. No, I mean, that's why just so, just to talk about the, like, the lawyer side, like, where it's like, you are a representative of democracy. Like, like, like you are, like, like.
A
So are we, though, as journalists. We're representatives of defenders of democracy too.
B
No, you're right. And now I'm like, as we're talking it out, I'm like, I was trying to come up with, like, a reason.
A
We don't sign any oaths, though. But do you sign an oath when.
B
You become admitted to the bar? You generally have to take an oath of office. It's called, and it's in front of a court. And it does say things like, I promise to uphold the law and like, administrate justice and do a lot of the things that arguably lawyers don't do all the time. So there is, there's like a pretty high level of intensity around, like, you know, you are representative of the US Democracy at its finest. And so perhaps that is, like, why some of these young lawyers, especially left. But you're right, like, journalists have, are trained to like, a really high standard of ethical conduct too. And so it's surprising. I mean, not surprising, but it is curious that there's this particular exodus of lawyers. And it's not clear that there's been a similar exodus in these other industries. Yeah.
A
I mean, it's funny, you have attorney client privilege. We have off the record that finds us. It's obviously different. I think yours is illegal, where you can actually be sued. If, if we break off the record, there's no suing. It's just our reputations and we lose our sources. Right.
B
So it's true. There's a lot of similarity. The more that we talk about it, the more I'm like, wow, there's a lot of similarities. And I, I found this already in writing or just like writing news pieces and going through fact checking and stuff. The first time I went through a really intensive fact checking process with multiple layers of fact checking. For a news piece I was publishing, I was like, oh, this is so easy. I did this all the time as a lawyer. That kind of intensive level of making sure things are right and citing everything is deeply familiar to me as a lawyer. They're very compatible. Professions in a lot of ways.
A
Yeah. I could tell from your writing in your piece in the New Republic, which everyone should check out. It is called. Hold on one second, let me get it. The lawyers who gave up big money to fight Trump. Not that many of them. Teaser. What does that say about the Times? But tell me what these new firms look like anyway.
B
Yeah. So interestingly, after all the stuff we talked about, after all the, like, big law firms capitulating, there was this little mini cre, I don't know, creation of several new little organizations or like wings of existing organizations that are expressly devoted to kind of defending the rule of law. And so for instance, one of them is a, is Lowell and associates of who you were just talking about. And he scooped up two of the associates who Squit who quit from Skadden in protest, which is a big law firm that capitulated and has made a name for themselves kind of representing like high profile public figures who are, were either, you know, Trump tried to fire or in other ways were like fighting for the kind of integrity of their jobs. Like Lisa Cook of the Federal Reserve Board.
A
Right.
B
And so they like who's being investigated for mortgage fraud.
A
Right.
B
Yes, I believe that is the case, though it seems, I mean, like, I, I'm sure her representation and as it seems to be outside it is primarily a politically motivated.
A
Right.
B
Matter. No. And so that's one, the Washington Litigation Group is another one which is representing, is like brand new and is representing similar kinds of cases. But basically there's like been a couple of new little startups, I guess is the right word, that are really taking on this fight that the big law firms would not and like fighting for specifically for the rule of law for like cases where it feels like the power of the executive offices abusing the legal system for political ends, Basically.
A
Yeah. So is there any good that can come out of all of this?
B
I mean, this, what I'm talking about, feels like a weird good silver lining. I mean, as we were talking, will.
A
It continue, though, after a Trump administration if Democrats are in office?
B
I don't know. I think, I mean, look, I barely knew what Trump was going to do last week, let alone what's going to happen in the next three years. So. So predicting what happens after Democrats get back in office is like beyond my current predictive. Right, Right. But I will say that generally law firms don't go away or even pop up overnight. So that's why this is so striking is because so many of these new ones were created, but lawyers and law Firms are not like, it's not a really agile industry. You know, it's not like startups or tech or something where there's, like, new companies being born and going away every two seconds, like, they're slow to move. And so I kind of expect that if these firms continue to pick up these fights, they're going to keep hiring people, they're going to be around, and then they're going to be big enough that they're not going to just go away overnight if in several years a Democrat ends up in the executive office. So I think it probably is not like a watershed change in the way that the whole industry operates, but I think it is like a little bit of a new thing that's going to stick around.
A
I mean, let's be serious. You've already heard Abbey Lowell say that Attorney General Bondi has carried out Trump's wrongdoing more than any attorney general since John Mitchell with President Nixon. So I've got to think that these firms might be also investigating Trump administration officials after his term, much like he is doing to Biden and Obama administration officials. Right.
B
You mean that a future Democratic president would hire them to help investigate stuff? I disagree. I don't think they'll be doing that. I think they are like, I think doing an affirmative investigation of someone like that is a very different matter from representing someone defensively in a legal action. And I think that these firms are. It's just like a different competency. So, like, let alone that, setting aside the politics of it, they're not set up to do that kind of thing.
A
Right. I mean, maybe they would be retained by the president if that was what they wanted to do.
B
Maybe, though, again, is it just a different. It's like a different world of legal stuff. I mean, maybe I'll eat my words. Maybe, maybe everybody will just be the same in another three years. But I kind of suspect that these firms are not going to serve that particular function in three years. I think they are.
A
Maybe they'll be defending Pam Bondi.
B
I think unlikely. But again, who knows? We'll find out.
A
Right?
B
I do think, like, these firms specifically on their site, they say, you know, we are devoted to defending the rule of law and to at least lawyers, at least to me right now, how that means something and they're signaling a particular thing. And that doesn't just mean going after Republicans. It means defending the integrity of the system as a whole. And so perhaps they'll all change. Like, like, certainly politics seems to influence absolutely everything. But I would be surprised because it would really sacrifice these specific lawyers reputations. And they seem to have hired a lot of zealots, you know, a lot of people who are like zealous about the rule of law and so they would be throwing their own careers in a FL hired to do that.
A
They could also create a podcast company on top of all of that, I'm sure.
B
Oh, abs, that. That totally. I think, to be honest, I think more lawyers should like, invest in talking to the public. I think there's a real dearth of understanding among people as to how the law works. So I'm all for that. If they want to create podcast companies, by all means, go for it.
A
Yeah, it could help their reputations. Thank you so much for that, Matthew. I'm gonna have to wrap it up because I think my dog is having a panic attack.
B
Oh, I'm so sorry.
A
And I'm not going to drug her as other friends of mine drug their do. Apparently everyone's dog's on Xanax now. She has an anxiety little belt on her. But no, I don't know.
B
Well, yeah, by all means, go, go soothe your anxious dog. I do not want to be the source of more anxiety for.
A
Yeah, yeah, Pancetta, she's, she's off the charts. But this was a really interesting conversation. Thank you so much for coming on the show and I hope everybody who is listening feels like they know more about possibly a movement afoot of, you know, law of really, you know, future ace lawyers and current, you know, associates and lawyers who are giving up money to fight Trump. I mean, says something, you're not seeing it in another industry.
B
So yeah, I mean, it was a great conversation. Thank you so much for having me. And I will say if anybody, like just to plug myself too, if anybody would like to know more about legal stuff in particular, feel free to join me on my media social substack too, which is called should you care. And specifically my purview is kind of talking about explaining legal stuff for non lawyers, which I feel like is a pretty needed thing these days.
A
So, yeah, thanks so much. Yeah, check out his substack. Should you care. And I should note that there are a lot of journalists who have left their companies because of, you know, clashes in terms of editorial content. But usually it's the company that pushes them out. Right? It's not, not always that they go out on their own. Obviously I started my own company with my own independent vision. Wasn't necessarily because an editorial clash, but because I have a different view and, and it's not necessarily because I'm thinking, oh, this is designed to go after Trump specifically. You know, this is independent media, investigative media. But it is happening. But it does feel like it's a little bit more of the people who are not fitting in with the culture are being pushed out with a wave of new shareholders and leaders that are, that care more about, you know, surviving in a Trump administration. So it is, in some ways it's similar.
B
Yeah, for sure. I mean, I, as I said, the more we talked about the before, the more I was convinced that the two professions are very similar in a lot of ways. But I agree, it doesn't feel like the lawyers, perhaps I'm just more aware of it because I am a lawyer. But it feels a little bit like, like there's momentum in this direction. I'm not sure if in journalism it feels like there's momentum in that direction of, like, leaving organizations. So I think that that's maybe where it feels a little different for me.
A
Right. Well, thank you so much for your time. I really appreciate it. And thank you to catch up again soon when there's any update.
B
Yeah, sounds great.
A
That was another episode of the Tara Palmeri Show. Thank you so much for tuning in. Please, like, subscribe. Leave a comment Share this with your friends. I would love to hear what you think about this episode. Very thought provoking and it really makes me think too, about the media and why so few have really stood up as well. I want to invite you to support my independent journalism. I am not controlled by shareholders or corporate boards who are in compliance with Trump and want to have a good relationship with the White House. So you can go to tarapaulmieri.com that's T A R A P A L m e r I.com to support that. I write whatever I know and know to be the truth, thanks to my sourcing and relentless investigative journalism. You can support that by joining the Red Letter. It is a community that I am building based on trust. And yeah, please become a subscriber. It's a way to get my exclusive reporting straight to your inbox as well. I want to thank my producer, Eric Abenate. I want to thank Abby Baker, who does the research and social media. And I want to thank Adam Stewart, who handles my graphics. I will see you again tomorrow.
B
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Episode: The Lawyers Who Gave Up Millions to Fight Trump
Host: Tara Palmeri
Guest: Matthew Wallen (ex-WilmerHale attorney, legal journalist)
Date: October 27, 2025
This episode explores the unprecedented phenomenon of elite lawyers leaving lucrative “Big Law” positions to stand against Donald Trump’s legal pressures on the profession—the ethical, economic, and institutional ramifications of law firms capitulating to Trump, the challenges and risks facing those who resist, and the small but significant rise of new rule-of-law-focused legal startups. Host Tara Palmeri and guest Matthew Wallen examine whether these lawyers’ revolt signals a broader crisis within American institutions expected to uphold democracy.
“I feel like I'm a writer fundamentally...I find it more interesting to communicate with non-experts...particularly with law stuff. Legal stuff is very important nowadays…but lawyers are by and large pretty terrible at explaining it.” (02:29–03:20)
“There is this kind of democratic lawyerly ideal…[but] you are often working on behalf of the highest paying clients…It’s kind of on the fringes with pro bono where the firms provide a venue for lawyers to invest time in things that they care about.” (07:12–08:42)
“If Trump is surprised at his own success, you know that it really must have been weak ground, because he is not a man who tends to be surprised at his own success.” (09:57)
“Lawyers…tend to use litigation as a route to settlement…With lawyers, it tends to be a bit more of a negotiation tactic.” (11:31–12:08)
“These deals…generally involve a commitment to contribute a ton of pro bono…to Trump’s causes…very vague, which is part of the problem.” (14:26–15:33)
“I think it's a betrayal of legal ethics. Lawyers are supposed to uphold the rule of law…to roll over and capitulate to that without even a fight is a pretty big betrayal.” (16:34–17:22)
“Seeing big law firms capitulate…has had a chilling effect on anybody else who was trying to get representation…against the President.” (17:32–18:16)
“Reputation among these firms is kind of everything…you don't want to screw that up…It's going to be really interesting to track in the coming years, how these firms evolve.” (19:17–20:10)
“It takes a real conscious effort to turn away from this kind of opportunity.” (20:21–21:23)
“To leave is a huge personal and professional risk…not a super hireable quality from most companies and places." (23:04–23:44)
“Law firms don't go away or even pop up overnight…so many of these new ones were created, but lawyers and law firms are not a really agile industry…it's going to stick around.” (30:24–31:41)
This episode offers both an insider’s account and an institutional analysis of why elite law firms caved to presidential pressure, the ethical and professional quandaries involved, and who is actually fighting for the rule of law in America’s fraught political era. The dialogue between Palmeri and Wallen is sharp, personal, and grounded in the realities facing both established professionals and those daring enough to build something new.
Wallen’s mantra: new organizations defending democratic norms are a rare “silver lining”—but whether they endure will hinge on the next generation’s appetite for risk and on the evolution of American democracy itself.