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The Daily

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

29 Dec 2025

Transcription

Chapter 1: What prompted Thomas Sipp to resign from his law firm?

0.031 - 28.958 Unknown

How does tennis superstar Naomi Osaka unwind? And how does New Zealand rugby legend Roko Thoko build camaraderie among his team? Hi there, I'm Isabella Rossellini, and in the final episode of This Is Not A Beauty podcast from L'Oreal Group, we speak to some of the world's greatest athletes to dig into how beauty shapes sports. Listen now on your favorite podcast platform.

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31.621 - 55.186 Michael Barbaro

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 Sipp, the lawyer who quit his job at a prestigious corporate law firm after his bosses gave in to legally dubious demands from President Trump.

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55.927 - 80.697 Michael Barbaro

And we hear how Sipp 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...

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81.385 - 94.129 Michael Barbaro

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?

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95.155 - 117.272 Thomas Sipp

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.

117.913 - 130.047 Thomas Sipp

It's not only 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.

130.367 - 143.522 Thomas Sipp

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.

144.059 - 145.423 Unknown

Can you just explain that?

145.443 - 170.51 Thomas Sipp

Yeah. I mean, there were difficult days for sure. You know, whether it's not being able to make friends, being made fun of for 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.

Chapter 2: How did the political climate influence law firms' decisions?

321.021 - 335.425 Michael Barbaro

Yes. 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.

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335.489 - 360.923 Thomas Sipp

That's right. And Skadden really advertised two things. It's pro bono program and it's 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 it's a big deal that Skadden does that because not many other firms do.

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361.544 - 369.054 Michael Barbaro

So when did you start to understand that Skadden had entered the president's crosshairs?

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369.935 - 386.438 Thomas Sipp

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 issues.

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386.705 - 396.741 Michael Barbaro

Right. I believe the claim was that these law firms may have practiced discrimination through the application of diversity, equity, and inclusion practices.

396.761 - 416.894 Michael Barbaro

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 Coie from interacting with the federal government. And so the people who work at these firms fear that they may go out of business.

417.515 - 441.45 Thomas Sipp

Right, yeah. And one of my friends from the firm 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.

441.43 - 464.282 Thomas Sipp

And during that preceding week, there had been pockets of the law firm trying to organize some sort of 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 worked there feel about what's going on and how so many of us believe that it's unconstitutional.

465.005 - 465.766 Michael Barbaro

The executive orders.

Chapter 3: What was the reaction to Skadden's deal with President Trump?

682.272 - 713.474 Thomas Sipp

This is... giving the president a PR win after being bullied. So it seems like I'm working at a firm that isn't as high caliber as it said it was. 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.

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713.775 - 727.156 Thomas Sipp

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.

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728.278 - 729.54 Unknown

So what did you do?

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730.111 - 751.458 Thomas Sipp

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 it actually look like? And I started thinking about it and finding answers, and so the questions became statements. And I realized what I had written was a draft of a resignation letter.

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752.079 - 753.781 Unknown

Not necessarily what you set out to do.

754.462 - 754.802 Thomas Sipp

No.

756.571 - 760.397 Michael Barbaro

Can I ask you to read from parts of the letter?

760.958 - 790.071 Thomas Sipp

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.

792.134 - 815.653 Thomas Sipp

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.

Chapter 4: How did Thomas Sipp's background shape his career in law?

955.531 - 976.962 Michael Barbaro

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,

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977.752 - 1003.533 Michael Barbaro

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.

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1003.994 - 1014.888 Michael Barbaro

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?

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1015.448 - 1043.316 Thomas Sipp

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 threatened 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.

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1044.217 - 1045.919 Michael Barbaro

It does change who the firm is.

1046.48 - 1048.022 Thomas Sipp

Yes. In short. Yes.

1048.525 - 1068.913 Michael Barbaro

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?

1070.193 - 1097.45 Thomas Sipp

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 bet Well, of course I'm worried, I guess.

1097.51 - 1108.107 Thomas Sipp

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.

Chapter 5: What were the emotional impacts of resigning for Thomas Sipp?

1246.518 - 1272.029 Thomas Sipp

I remember that part. And it sounded like people generally liked, 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 it means to be an American. Other people reached out because they felt sort of Maybe a kinship, a sort of common background, whatever it may be.

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1272.069 - 1294.762 Thomas Sipp

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' position?

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1294.782 - 1306.099 Thomas Sipp

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 was like a wind in my back.

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1307.28 - 1310.265 Michael Barbaro

And what ends up happening to your job prospects? Do you end up finding a job?

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1310.706 - 1314.591 Thomas Sipp

Long story short, I do. I'm currently working for a federal judge.

1315.473 - 1322.443 Michael Barbaro

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?

1322.558 - 1343.014 Thomas Sipp

I can't tell you a lot, but I can tell you some things. Okay. The judge actually found me through his network and mine kind of colliding. 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.

1343.5 - 1360.891 Michael Barbaro

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.

1360.931 - 1377.878 Michael Barbaro

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.

Chapter 6: How has Thomas Sipp's life changed since leaving Skadden?

1496.675 - 1517.953 Thomas Sipp

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 mean something.

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1522.417 - 1526.58 Michael Barbaro

Thank you once again for your time and your candor.

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1527.725 - 1538.346 Thomas Sipp

The pleasure and the privilege is all mine. I really just want to say thank you because you're a huge part of what happened to me a few months ago. You changed my life.

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1539.749 - 1583.377 Michael Barbaro

Oh, well, you changed your own life. We just chronicled it. Today's Daily was produced by Olivia Nett, Shannon Lin, and Muj Zaydi. It was edited by Patricia Willans, Jodi Becker, and Michael Benoit. Contains music by Dan Powell and Marion Lozano, and was engineered by Alyssa Moxley, Rowan Emisto, and Chris Wood. Special thanks to Jessica Silver-Greenberg. That's it for The Daily.

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1583.397 - 1584.198 Michael Barbaro

I'm Michael Barbaro.

1585.479 - 1586.2 Unknown

See you tomorrow.

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