The Daily - Why One Lawyer Resigned When His Firm Caved to Trump: An Update

Episode Date: December 29, 2025

This week, The Daily is revisiting some of our favorite episodes of the year and checking in on what has happened in the time since.President Trump has used executive orders to wage war on law firms, specifically targeting those whose lawyers have investigated or sued him, or represented his enemies in court.Michael Barbaro speaks to Thomas Sipp, a lawyer who chose to quit after his firm, Skadden, negotiated a deal to placate the president.Guest: Thomas Sipp, a lawyer who left his firm after it negotiated a deal with Mr. Trump.Background reading: Listen to the original version of the episode here.Read about how Paul Weiss, a major democratic law firm, ended up bowing to Mr. Trump.Ever since the elite law firms Skadden and Paul Weiss reached deals with the Trump administration, top partners have closed ranks in support of the agreements.Photo: Graham Dickie/The New York TimesFor more information on today’s episode, visit nytimes.com/thedaily. Transcripts of each episode will be made available by the next workday.  Subscribe today at nytimes.com/podcasts or on Apple Podcasts and Spotify. You can also subscribe via your favorite podcast app here https://www.nytimes.com/activate-access/audio?source=podcatcher. For more podcasts and narrated articles, download The New York Times app at nytimes.com/app.

Hey, it's Michael. This week, the Daily is revisiting some of our favorite episodes this year, listening back and hearing what's happened in the time since they first ran. Today, we return to our conversation with Thomas Sip, the lawyer who quit his job at a prestigious corporate law firm after his bosses gave in to legally dubious demands from President Trump, and we hear how SIP views that moment now eight months later. It's Monday, December 29th.

Thomas, welcome to The Daily. Thanks for having me. I'm getting the small sense that this is a nerve-wracking experience for you even before it started. I'm just seeing it on your face. Yeah, it definitely is. I want to start by asking you to explain, Thomas, how it is that you came to be a lawyer in the first place and ended up at this very prestigious firm

where you worked until just a few days ago, Scadden Arps. What's that story? So going all the way to the start, I was born in Japan to an American father and a Japanese mother. And my family moved to the United States when I was 10. My parents separated shortly after, and so I was learning English in middle school

and also learning about what it means to be an American. suddenly becoming this sort of racial minority because I'm mixed race and coming to understand the social fabric that's kind of unique to the United States especially compared to a relatively homogenous country like Japan.

And, you know, growing up with my single mom who doesn't speak fluent English and getting all those sort of experiences, I think, started to put me on the path that I'm on now. Can you just explain that? Yeah. I mean, there were different days for sure, you know, whether it's not being able to make friends, being made fun from my accent and stuff like that, that really, I think, started to form, like, that sense

of injustice that I think fuels me sometimes, right? But at the same time, I moved to the United States, you know, in 2008 and during that election, and there's all this conversation in America about hopefulness and about, you know, this being a country where there's a place for for anyone right and so I was also absorbing that as well in high school I joined a debate team to practice public speaking and in college I was studying political science at the University of Texas and I had this wonderful opportunity to be an intern at the United States Senate. Wow. This was probably basically like a decade after I moved to the United States, and suddenly I'm walking through the halls of Congress

with my little yellow Senate intern badge and running into senators and congressmen getting to sit in on important hearings, and it's during that time that I really decided I want to be a part of this project here in the United States. And when you say this project, what do you mean? It's, you know, march towards justice, the betterment of everyone, I think there are these core principles that are unique to the United States in many ways.

I'm getting from you a real sense of idealism and a real pure admiration for what the United States represents. Yeah. I'm not blind to the errors in the past, and I know that the United States has not been and still is not a perfect country. But I really still believe that when the United States is doing the right things, the whole world is about. better place because of it. So talk about how this all translates into your decision to become a lawyer, to enter this industry. Well, so a lot of the people with the cool jobs in D.C. tend to have law degrees. And so I figured it was the next best step afterward. And so I go to law school straight out of college. All the law firms, the big law firms, almost by definition, pay the same scale salary. So the way that these law firms distinguish themselves from each other oftentimes

is in things like how their pro bono program operates, how invested they are into diversity initiatives. And I chose Scadden because it had the prestige. And as a 22-year-old trying to pay off a six-figure debt, I was drawn toward a higher salary, among other things. I'm just going to explain to people. Yes. By Scadden, you mean Scadden Arps. Scadden Arps, yes. Big, big law firm has an office here. New York has offices, I think, all over the world.

It's one of the firms that we think of when we think of this concept of big law, law firms that do a huge amount of work in corporate America. That's right. And Scadden really advertised two things. It's a pro bono program and its diversity initiatives. With regard to the pro bono programs, Scadden had a rule, basically, that said that, You can count an unlimited number of your pro bono hours towards your billable hours requirement. And it was a big deal that Scadden does that because not many other firms do. So when did you start to understand that Scadden had entered the president's crosshairs?

So on March 17th when the EEOC, which stands for the Equal Employment Opportunity Commission, basically published this letter listing 20 law firms including my own, saying that These law firms are essentially under investigation for their practices related to diversity. Right, I believe the claim was that these law firms may have practiced discrimination through the application of diversity, equity, and inclusion practices. Right. And these executive orders, I think it's worth reminding listeners, they can feel to the law firms that are being hit with them like death sentences

because they explicitly prevent these firms like Perkins Coup. from interacting with the federal government. And so the people work at these firms fear that they may go out of business. Right, yeah. And one of my friends from the firm sends me an article that the New York Times published, basically stating that Scadden was in talks with the administration to avert an executive order. And this was after Paul Weiss, which is essentially a peer firm, made a deal, including for $40 million pro bono commitment to causes that the president agrees with.

And during that preceding week, there had been, you know, pockets of the law firm trying to organize some sort of, you know, request from a response, nothing publicly, but at least internally seeking clarity and hoping to provide at least some input into what the attorneys who actually work there feel about what's going on and how so many of us believe that it's unconstitutional. The executive orders. Right. Like, this is not a difficult legal question. There's no legal basis for what the president is doing. complete abuse of power. And so we want our firm to stand up for that. But we're feeling like things are moving really fast and we felt voiceless. So what happens next? So there's this email thread that got around to parts of the firm. And so when I see that, I realize at that point,

that's pretty likely that there's going to be a deal and that it's going to be one that the attorneys don't like. And, you know, within hours, I think, we again find out from the news that there is this agreement, and then we hear from the firm. They have done a deal. Yeah. We'll be right back. I just want to summarize what is in this deal that Skadden reached with President Trump.

It promises to provide $100 million in pro bono legal services from Skadden to causes that both President Trump and the law firm both support. it calls for hiring what are known as Scadden Fellows. Those fellows are, at least some of them, supposed to be focused on Trump-friendly issues, and some of them have to be conservative in their ideological outlook. And then there's a part of the agreement that vows that Scaden will not engage

in, quote-unquote, illegal DEI hiring practices. Broadly, this is the deal that every major law firm that has come to an agreement has reached with the president. So what is your reaction to this deal when you finally digested? Personally, I felt ashamed

to work at Skadden and thus such a new experience because of how prestigious a law firm is and then suddenly in the blink of an eye in just a few days, hours even. Like my whole view of the firm has been completely tainted.

Can you just explain what precisely is making you feel the shame. You know, it's a mix of things. This is giving the president a PR win after being bullied. So it seems like I'm working at a firm that, you know, isn't as high caliber as it said it was, right? But more importantly than that,

so many lawyers agree that what the president is doing is wrong. This is a threat to our constitutional fabric, to our democracy, to our civil, liberties. People should be able to be represented by their lawyers freely. Judges should be able to make decisions, even if it goes against the president. And to see Skadden be complicit to aid this attack, I was so ashamed to work there. So what did you do? So I start actually just writing down notes and really my questions. Some of them are practical. Like, how is this going to be enforced, what will actually look like?

And I started thinking about it and finding answers, and so the questions became statements. And then I realized what I had written was a draft of resignation letter. So that's something like... Not necessarily what you set out to do. No. Can I ask you to read from parts of the letter? Yeah, of course.

Dear colleagues and friends, I'm writing to let you know that I am leaving this firm. There was a time when my employment here was so unlikely. For much of my early childhood, I was not a good student. I struggled to focus in class and take anything seriously. But even then, there was one subject I loved, history. I thought it was so wonderful to learn about all that came before me, about the triumphs and tragedies, about the moments of individual bravery

and collective complacency. I would often imagine myself faced with the same dilemmas. Why would I do if I was there? Would I do the right thing? It always felt like there was no way to know. I believe, as I know many of you do, that what the current presidential administration is doing

is wrong, that we were sliding into an autocracy where those in power are above the rule of law. Scadden's agreement with the Trump administration sent our country deeper down this dissent. And then I finish. Scadden is on the wrong side of history. I could no longer stay knowing

that someday I would have to explain why I stayed. what did it feel like to hit send I mean listen to your breathing right now it's like you're reliving it yeah what was it like to send that email if you heard my breath it felt like that maybe a hundred times more though

because I knew that you know that was a pivotal moment in my life maybe just as pivotal as coming to the United States in the first place. I knew that I was closing some doors and, you know, a place like Skadden, I'm grateful for that experience. I think it's only possible in a country like the United States,

and I really, really believe in it. I'm sure you're aware that many people who have spoken out against President Trump and his policies have experienced, at times, ferocious blowback. It can be a life-altering event. Is that something you're worried about now? Yeah, and I was finally able to talk to my mother

after resigning, and she's back in Japan, you know, with the rest of my family. And I told her I quit, and she was like, do you have another job? And I was like, no, mom, you don't understand, like, this is like in the news. and she sort of did a process at first and then she started to cry

and she asked me to come back to Japan and I said no I can't and I won't Many of your colleagues are not leaving their jobs they may feel the way you feel and have two kids they have to put through college they might not feel the way you feel

I'm thinking about reporting my colleagues did inside the upper echelons of Paul Weiss when that law firm did a deal with Trump and it became clear that the majority of the people who run the firm and lots of them felt that the best thing to do was to make a deal to protect the thousands of people who work at these firms and that at the end of the day what they're giving up is small compared to that survival

And the bosses at all these firms that end up capitulating to Trump say some version of, we are the same law firm after we did these deals as we were before. In fact, in a company-wide email, your former boss says just that. Quote, this agreement does not change who we are. What do you make of that? I just don't think that's true. these law firms are agreeing to these deals when they know that there's no legal basis

for any friend executive order and by capitulating they're aiding you know this existential threat against the profession the independence of the judiciary and our democracy and everyone who depends on it it does change who the firm is

in short. Yes. You very clearly have a lot of faith in the U.S., but at this point, how confident are you given everything you've just been through that the version of the United States that seems to be at the center of everything you've done here is now the version of the United States?

Confident because of what so many people, strangers, you know, reaching out to me, have said to me, which is that they're also scared. Everyone is scared But if everyone could You know stand up and speak up about this Then we can turn this back I think we can save it still

But are you a little bit worried That you're making the wrong bad Well of course I'm you know worried I guess You know I'm putting my career on the line For this and I knew that going into this I have student loans. I have a single mom who, you know...

And you just publicly picked a little bit of a fight with the president. That's right. I wonder if this experience made you question going into law. No, I don't regret becoming a lawyer. And going to law school. It's a wonderful education. You know, even my time at Scott, and I learned so much. and it's equipping me with skills, I think,

to advocate for what I believe in and for others as well. And that's what lorries do. Well, Thomas, thank you for coming in here and for telling us this story. We really appreciate it. Thank you. After the break, how Thomas has fared since he quit his job. Let's catch up.

Okay. Formally. Okay. You look well. You look rested. The last time you saw me, I was running on almost no sleeve. Well, catch me up on everything that's happened to you. Last time we spoke, it was just a few days after you quit your job at Scaden.

Right. Suddenly, you're not employed. You're not getting any paychecks. What happened next? I came on this podcast. I remember that part. And it sounded like people generally like. you know, what I said, and I got so many heartfelt messages from people, you know,

feeling that sort of hopefulness that I feel, thinking about these sort of democratic values, what I mean to be an American. Other people reached out because they felt sort of maybe a kinship, a sort of common background, whatever maybe. There were just some parents who were worried about their kids and, you know, listening with their kids, and those are some of the most touching ones. There was one in particular that really struck me. Can you describe it? Yeah. It was a father driving his kids to school. And they're listening to this episode. And he's asking his kids, what would you do? If you were in Thomas's position? Yeah, exactly. And that's the sort of thing that when I was a kid, I would think about in history

class. And I don't know. It was a really great feeling. And it gave me a real, it's like a win in my back. And what ends up happening to your job prospects? Do you end up finding a job? Long story, sure, I do. I'm currently working for a federal judge. And what can you tell me about that work, how you got it, and how it may or may not fit into the way that your last job ended? I can't tell you a lot if I can tell you some things.

Okay. The judge actually found me through his network and mine, kind of colliding. I'm his, the title is I'm a law clerk, and the job is essentially, analyzing the law, explaining it, making recommendations to the judge. So you're basically the judge's assistant. I know when you clerk for a judge, this is my sense, you may not be able to discuss a lot of the intricacies of your work. But it strikes me that if you're working for a federal judge, you're potentially interacting with President Trump's agenda to some

degree. And federal judges are the figures in our legal system right now who are seen as really the most powerful and important potential checks on this president. And I'm sure that hasn't escaped you either. I'm, to be honest, I'm not going to talk about, you know, active cases that may or may not be before my judge. It's because there's pretty serious ethics concerns about, you know, clerks typically don't talk to the media. Right. And I want to make it clear that the judge's job isn't to be a partisan actor. It's to be the adjudicator of what the law says. And as, you know, my judge's clerk, that's also my job and responsibility.

And I take that really seriously. Right. And I think the true interpretation is that, you know, I made this decision on ethics grounds. It was about what I thought, you know, the law was what the Constitution demands. and I was just hoping to explain my own decision in a time when I think a lot of people were facing a similar decision and they weren't sure

what it would look like on the other side and I guess right now I'm speaking to you from the other side of that decision to say I was fine I was actually more than fine there is another side to quitting a big prestigious, well-paying job at a law firm

on principle. Yes. And in the year 2025, you'll end up all right. And specifically speaking to the lawyers,

not everyone in America can safely speak their mind right now. But lawyers can. Obviously,

you may be targeted. But the law firms that fought back and are winning in courts are doing fine financially. They're not

going going underwater, and this, I think, existential fear was completely overblown. It was overstated. I think so. It was a excuse. I think it was putting profits over an oath that lawyers swear to protect the Constitution. And, you know, if someone like me ends up fine, more than fine, then the executive partners and chairpersons of these law firms...

Who make many millions more. Right. would have been completely fine too. And regardless, I think the oaths have to me something. Thank you once again for your time and your candor. The pleasure and the privilege is all mine. I really want to say thank you

because you're a huge part of what happened to me a few months ago. You changed my life. Oh, well, you changed your own life. We just chronicled it. Today's Daily was produced by Olivia Nett, Shannon Lynn, and Muj Zady. It was edited by Patricia Willans, Jody Becker, and Michael Benoit. contains music by Dan Powell and Marion Lozano,

and was engineered by Alyssa Moxley, Rowan Amistow, and Chris Wood. Special thanks to Jessica Silver Greenberg. That's it for the daily. I'm Michael Bobaro. See you tomorrow.