The Daily - ‘I Felt Ashamed.’ Why One Lawyer Resigned When His Firm Caved to Trump

Episode Date: April 7, 2025

Over the past few weeks, 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 they negotiated a deal with Mr. Trump.Background reading: 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.For more information on today’s episode, visit nytimes.com/thedaily. Transcripts of each episode will be made available by the next workday. Photo: John Taggart for The New York Times Unlock full access to New York Times podcasts and explore everything from politics to pop culture. Subscribe today at nytimes.com/podcasts or on Apple Podcasts and Spotify.

From the New York Times, I'm Michael Bobarro. This is The Daily. This is an absolute honor to sign. The president signed an executive order singling out Perkins Coe. What they've done is just terrible. It's weaponization. Over the past few weeks, Donald Trump has used executive orders to wage war on law firm after law firm. Those who made the list are real murderers row, including Covington and Burling.

Paul Weiss, General Block. Big law, white shoe firm, some of the best lawyers in the country. Specifically targeting those whose current or former lawyers have investigated him, sued him or represented his enemies in court. But rather than fighting Trump, many of those firms have buckled. President Trump yesterday rescinded an executive order targeting prominent law firm Paul Weiss. Milbank joins firms Wilkie Farr and Gallagher, which also cut a deal. The question left in the air, of course, is who's next?

Negotiating deals that give Trump much of what he wants and forcing thousands of the lawyers who work at those firms to make a choice. Remain at firms that have capitulated, or quit in protest. Most have chosen to stay. Thomas Sipp chose to quit. Today, I asked him to explain why. It's Monday, April 7th. Yeah, come on in. Put on these headphones.

These. I think, yes, those. Comfy? Yeah. Good. Thomas, welcome to the Okay. Comfy? Yeah. Good. 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. We have been trying here at The Daily for a few weeks to understand what it's like to work at one of the law firms that's now at the center of President Trump's campaign of retribution. And to have watched from within those firms as one by one by one, these very big and powerful firms have capitulated to the president's pretty unusual demands. And it may not shock you to learn this, but attorneys at these firms are pretty reluctant to talk about that, and you are the rare exception.

So thank you for being the exception. I really appreciate it. 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, Skadden 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, you know, I was learning English in middle school and also learning about what it means to be an American. Because before that I was really, you know, just like a native Japanese kid. And was through that experience, including of 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 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 difficult days for sure. I think even though this week has been very difficult for me, I still look back and think of some of the days that I experienced as a kid in middle school. Whether it's not being able to make friends, being made fun of for my accent, stuff like that, that really I think started to form that sense of injustice that I think fuels me sometimes.

Right? What was the first real injustice you can remember as an immigrant, not really knowing English, navigating this new world? I think there was a time when I was in math class. And, you know, math is the same, so I could answer the questions. And I think one of the answers was 33. And you could probably tell that I paused even before I said it. It's because back then I would have pronounced it differently because I couldn't pronounce TH.

And the whole class laughed, even though it's the right answer. But then I would go home and I would close my door, put my book back down, and just practice words that I couldn't pronounce, like 33. I'd just say it over and over and over again. Other words like world, these basic words that come up in everyday dialogue. And that was part of my experience.

But at the same time, I moved to the United States, you know, in 2008, 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 anyone, right? And so I was also absorbing that as well. So at the precise moment that you are struggling with your identity and recognizing that you are different from other people, and it sounds like feeling at times a lot of shame around

that, you're seeing the United States elect Barack Obama, like you, the product of a biracial marriage, and somebody who in that campaign you're describing invites the whole country to have this really honest conversation about identity and about race. And he talks about, and this is from his 2004 DNC speech, but it's one of my favorites, And it talks about being like a skinny kid with a funny name. I remember other parts of the speech too, because it just sticks with you. In high school, I joined a debate team to practice public speaking, try to get over that fear. That was part of also, I think, my path to being a lawyer. 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, you know, 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 a march towards justice, the betterment of everyone. I think there are these core principles that are unique to the United States in many ways. If it's not unique, then it's something that the United States really has the potential, maybe more than any other country on earth, to embody, which is that this is a place where anyone can come work hard and be an American. Yeah, 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 a better place because of it. So talk about how this all translates into your decision to become a lawyer, to enter this industry. Right.

Well, so picking back up where I was just sent an intern in DC, I'm looking around and seeing that a lot of the people with the cool jobs in DC tend to have law degrees, or they're actively practicing law. So I figured it was the next best step afterward. And so I go to law school straight out of college. I get into a lot of law schools and I'm balancing offers.

The exercise a lot of incoming law students have to do when they're admitted is balance the prestige of the law school versus how much money they're offering you. And I chose Columbia Law School because they gave me a pretty good balance. And, you know, like many other law students, I cover the balance with student loans. And that starts to take us to the next steps. As a 22-year-old trying to pay off a six-figure debt, I was drawn toward a higher salary, among other things. 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 their billable hours requirement

operates, how invested they are into diversity initiatives, and how actively their affinity groups recruit on law schools. And I chose Skadden because it had the prestige. I'm just going to explain to people, by Skadden you mean Skadden Arps? Skadden Arps, yes. Big, big law firm has an office here in 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. Mm-hmm.

That's right. And Skadden really advertised two things. Its pro bono program and its diversity initiatives. With regard to the pro bono programs, Skadden had a rule basically that said that you can count an unlimited number of your pro bono hours towards your billable hours requirement and the billable hours you know kind of represents two things though if you meet the requirement you get a bonus at the end of the year so that's more money and then you're also

in good standing right you're doing enough work you know you're meeting your hours and it's a big deal thatlon does that because not many other firms do. Right. And if I know my law firm culture well, what that means is that charitable legal work that this firm does counts against you being a successful lawyer there, which probably means to a young idealistic lawyer like you, it means that yes, while you're going to work at a big hard charging corporate law firm, that that law firm is putting pro bono work, work for people who can't afford lawyers at the center of its culture.

Yeah, exactly. I worked on, I'm just going to speak prolly on this, but matters related to unhoused people, immigration, and police misconduct. Aaron Powell Did you win any of those cases? Did you win all those cases? Michael S. Lauer I can't say. Aaron Powell But the smile on your face makes me think that you might have prevailed on behalf of some of those clients.

When we were texting today, because I needed you to get here on time, you mentioned that you live essentially next door to the law firm and that doesn't seem like an accident. Yeah, that's right. I decided to pay a little bit more in rent for a slightly worse apartment, just so I can be close to the office. How close? I'm talking like a five-minute walk. So you could just be there all the time?

Yeah. Obviously, you know, at a big law firm like this, it's challenging work, it's long hours, high-pressure environments. You're closely scrutinizing, you know, the grammar and all of your sentences that you write, even in internal emails and all that stuff, because it, you know, it can affect your reputation and your credibility. But at the same time, in those long hours and in this high-pressure environment, you make friends really quickly. And there are great mentors out there too who I learned from. So actually, I liked going into work every day. If you ask people who I worked with, I'm sure they tell you I was often there very early and late.

But that's partly because I just want to say good morning and good night to everyone in my hallway. So, when did you start to understand, Thomas, over the past many weeks, that Skadden 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 I think it was the following weekend on that Sunday in the afternoon, one of my friends from the firm sends me this tweet. Basically, it's a thread posted by Dinesh D'Souza. The right-wing activist. Mm-hmm, the right-wing activist. Basically discussing how Skadden is representing a client against him related to this widely debunked conspiracy theory documentary about the 2020 election. Right, that D'Souza had made.

Yes. And Elon Musk tweets on that thread saying something along the lines of, you know, Skadden just needs to stop. So there's a letter and then there's this tweet. And while all this is happening, there are other law firms that are dealing with similar things, including Perkins Cooey, who was hit with a executive order earlier in the month. 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 Cooey from interacting with the federal government. And we talked about this on the show. If these firms represent any corporation or entity that needs the federal government and many big companies do, suddenly they can't really effectively represent them. And in that sense, the people who work at these firms fear that they may go out of business. Right, yeah. And Thursday comes around, my friend again sends me an article

that the New York Times published, basically stating that Skadden 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. So what are you and the people you work with thinking as you're watching this happen? We're not necessarily surprised, but we're still shocked. And during that preceding week, there had been pockets of the law firm trying to organize some sort of request for a response, nothing publicly, but at least internally seeking clarity and hoping to provide at least some input into what the attorneys who actually

worked there feel about what's going on and how so many of us believe that it's unconstitutional. The executive orders. Right. And you want to communicate that to your bosses. Yes. During this month, there are law firms that are fighting back, right? There are law firms that take on representation of the law firms being targeted, right? Which puts them at risk, but they're willing to say, hey, we know what's right.

And we see that that's being celebrated within the legal community and targeted, right, which puts them at risk. But they're willing to say, hey, we know what's right. And we see that that's being celebrated within the legal community. And it's like, this is not a difficult legal question. There's no legal basis for what the president's doing. It's complete abuse of power. And so we want our firm to stand up for that. And a lot of associates, I think even partners, would feel betrayed by an agreement.

So that's what we're trying to express. But we're feeling like things are moving really fast and we felt voiceless. So what happens next? So then this Friday, there was this email thread that got around to parts of the firm. And the discussion is basically should attorneys still have access to the firm-wide distribution lists, which is basically these mailing lists that allow attorneys to ask questions broadly to the rest of the firm or communicate broadly. 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 within hours, I think, we again find out from the news and from President Trump's, probably, I think it's like true social. True social. Yeah. 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 SCADN to causes that both President Trump and the law firm both support. It calls for hiring what are known as SCADN 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 Skadden 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 that's such a new experience because of how prestigious the law firm is. And then suddenly in the blink of an eye and just a few days, hours even, my whole view of the firm has been completely tainted. Can you explain why? Is it the fact that the firm agreed to this? Is it the specifics around pro bono work, which I know is so important to you?

What precisely is making you feel the shame? 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. Hmm. Right? But more importantly than that, so many lawyers agree that what the president is doing is wrong. Trying to

punish his enemies and then coerce any law firm who he perceives as an enemy to either himself or to his circle from being able to represent clients who might be against them. And this is happening in a much bigger political climate where there's fear spreading. When a judge makes a decision that goes against the president, there shouldn't be politicians calling for their impeachment. Right, but that's what's happening right now. That's what's happening. 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 on Sunday night, 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 it actually look like? You're kind of writing to your bosses. Right, what do these words mean? And a lot of the questions, 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 a resignation letter. So that's something. Not necessarily what you set out to do. No. And Monday comes around, and I have some conversations, you know, in the office with other attorneys. And my friends and trusted mentors and colleagues, I just wanted to hear what people had to say and think.

And everyone's distraught. 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. What 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 are sliding into an autocracy where those in power are above the rule of law. Skadden's agreement with the Trump administration sent our country deeper down this descent. And then I finish. Skadden is on the wrong side of history. I can 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. If I might add, I grew up with two sisters, a twin sister and a younger sister. And my parents asked us back in Japan whether we wanted to move to the United States

so that we can learn English. Actually, that was the reason why. And I remember just thinking like, I was scared. I don't speak English. But I was the one from my sister's who said, like, I think we should. And my parents let us choose, you know? And it felt like that, too. I knew that I was closing some doors in a place like Skadden, like, for that 10-year-old kid, he had no idea where

he might end up. And 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 know not everyone can make this decision, including even those in my law firm. There are people who have families who depend on their income,

who can't just quit on a dime like I did without a job lined up. There are people who are here at the law firm on work visas because they're not United States citizens. And like those people can't really speak out because of this climate of intimidation. Everyone has their own reasons, I think. And I just want to say thank you to all the people

who read my resignation letter. There have been. I mean, you didn't, we should say, mean for this letter to become. As public as it did. It kind of just happened. Right, well, and I knew that in putting in writing, there was a risk, but I sent it to my immediate colleagues

and then it was posted online the following day. 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, telling her that I quit because I hadn't talked to her about my thoughts

since it all happened so fast. And she's back in Japan with the rest of my family. And I told her I quit, and she's like, do you have another job? And I was like no mom you don't understand like this is like in the news And I quit because of what's going on in America right now. That's the question my mother would ask me. Yeah And she sort of did a process at first and then she started to cry she realized what's happening and She asked me

To come back to Japan. I said, no, like I can't and I won't. I made this decision because I believe that there's still hope and I owe it to America, I think, to stay here and speak out on this issue. Many of your colleagues are not leaving their jobs. And there's a spectrum of reasons that you've started to hint at about why they're not leaving. 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, lots of them, felt that the best thing to do was to make a deal. And the reason that they articulated, they felt that way, is that in their minds, they had to protect the thousands of people who work at these firms. They may have hated the deal. Some of them no doubt hate the deal.

But they felt their job was to make sure that these firms survives, lives through this period of time. 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 threat in executive order. And to the extent that these firms feel an existential threat to the firm itself by capitulating their 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. Yes. In short. Yes.

I think all of these firms that are making these deals and defecting, they're worried about losing clients to a peer firm that's connected to the administration already and these firms are betting on the president to succeed, right, from a PR perspective, because they can say, look, it was a smart deal. But the smart deal is with this president who is trying to actively undermine our profession and our democracy.

And for the firm to say, hey, it doesn't change who we are, I think it fundamentally does. You very clearly have a lot of faith in the US. That's just been evident throughout this entire conversation. And your decision to quit seems to be grounded in the sense of what is the best version of what the US can be in your mind. But at this point, how confident are you, given everything you've just been through? is the best version of what the US can be in your mind. 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, 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 bet and that maybe the law firms as much as it might pain you to Think about it this way are making the sound bet in this moment 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. I mean, law is one thing in theory. And then it's another thing in practice, especially at these big law firms.

These are not nonprofits. Right. And that's part of the decision I made when I was in law school, finding a job, my first job. And to ask your ultimate question, no, I don't regret becoming a lawyer and going to law school. It's a wonderful education. You know, even my time at Skadden, I learned so much.

And it's equipped me with skills, I think, to advocate for what I believe in and for others as well. And that's what Louries do. Well, Thomas, thank you for coming in here and for telling us this story. We really appreciate it. Thank you. On Friday, hundreds of firms threw their support behind the first firm to be attacked by President Trump, Perkins Cooey, which has sued the administration to stop Trump's executive order against the

firm. In a legal filing, the hundreds of firms wrote that Trump's crackdown on Perkins Cooey and the entire industry, quote, poses a grave threat to our system of constitutional governance and to the rule of law itself. But many of the country's biggest and most profitable firms refuse to sign the briefing, including Thomas's former firm, Scadden Arps. We'll be right back. Here's what else you need to know today.

A federal judge has ordered the Trump administration to bring back a migrant it mistakenly deported to a notorious prison in El Salvador by tonight, something the White House said in response that it has little power to do. That prompted the judge to declare that the administration's conduct, quote, shocks the conscience. But instead of trying to fix its error, the White House has instead punished a government lawyer who acknowledged the deportation was done by mistake by placing him on administrative leave over the weekend.

And. Large scale protests against President Trump and his agenda were held in cities and towns across the United States over the weekend, attracting hundreds of thousands of demonstrators. Donald Trump has got to go! Participants said they were marching to oppose Trump's policies toward federal workers, public education, immigration, tariffs, and public health, and to fight back against Elon Musk's Department of Government efficiency. Speakers at the rallies, including former Republican Congressman Eric Swalwell, said

that Trump has become a disaster for the country and its finances. As you stand here right now, we have gone from a Trump slump to a Trump train wreck. Our 401ks are 201ks. Our costs at Walmart, Home Depot, and Target are going up. And where is Donald Trump? He's golfing! So to Donald Trump I say, get your ass off the golf course and face the people!

Today's episode was produced by Olivia Nett, Shannon Lin, and Mood Sadie. It was edited by Patricia Willans and Michael Benoit, contains original music by Dan Powell and Marian Lozano, and was engineered by Alyssa Moxley. Our theme music is by Jim Brunberg and Ben Landsberg of Wonderly. Special thanks to Jessica Silver Greenberg. That's it for the Daily. I'm Michael Bobarro. See you tomorrow.