Why One Lawyer Resigned When His Firm Caved to Trump: An Update
Episode
24 min
Read time
2 min
Topics
Career Growth, Leadership, Philosophy & Wisdom
AI-Generated Summary
Key Takeaways
- ✓Standing on principle: Sip resigned from Skadden within hours of learning the firm agreed to provide $100 million in pro bono services to Trump-approved causes and hire conservative fellows, viewing the deal as constitutionally baseless capitulation to executive overreach.
- ✓Career consequences myth: Despite fears of professional ruin, Sip secured a federal clerkship position shortly after resigning, demonstrating that lawyers who resist on ethical grounds can find alternative career paths and that law firm survival fears were overstated excuses prioritizing profits over constitutional oaths.
- ✓Collective action potential: Sip argues that widespread fear among legal professionals creates opportunity for resistance, asserting that if lawyers collectively stood up against unconstitutional demands, they could reverse democratic backsliding, as law firms that fought back in court remained financially stable.
- ✓Immigration perspective on democracy: As a Japanese immigrant who arrived in America at age ten speaking limited English, Sip developed his commitment to constitutional principles through experiencing both discrimination and the hopeful promise of American democracy during the 2008 election cycle.
What It Covers
Thomas Sip, a lawyer who resigned from prestigious firm Skadden Arps after it capitulated to Trump administration demands on DEI practices, reflects on his decision eight months later and his subsequent career path.
Key Questions Answered
- •Standing on principle: Sip resigned from Skadden within hours of learning the firm agreed to provide $100 million in pro bono services to Trump-approved causes and hire conservative fellows, viewing the deal as constitutionally baseless capitulation to executive overreach.
- •Career consequences myth: Despite fears of professional ruin, Sip secured a federal clerkship position shortly after resigning, demonstrating that lawyers who resist on ethical grounds can find alternative career paths and that law firm survival fears were overstated excuses prioritizing profits over constitutional oaths.
- •Collective action potential: Sip argues that widespread fear among legal professionals creates opportunity for resistance, asserting that if lawyers collectively stood up against unconstitutional demands, they could reverse democratic backsliding, as law firms that fought back in court remained financially stable.
- •Immigration perspective on democracy: As a Japanese immigrant who arrived in America at age ten speaking limited English, Sip developed his commitment to constitutional principles through experiencing both discrimination and the hopeful promise of American democracy during the 2008 election cycle.
Notable Moment
After publishing his resignation letter, Sip received messages from parents listening with their children who asked what they would do in his situation, mirroring the exact thought experiment he conducted as a student studying history.
Episode Transcript
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 29. 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 wanna 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. Mhmm. 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. It's not like becoming this sort of racial minority because I'm mixed race. And just coming to understand the social fabric that's kind of unique to The United States, especially compared to a relatively homogeneous country like Japan. Right. And, you know, growing up with my my single mom who doesn't speak, you know, 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. 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. 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. Mhmm. 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 a 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, important hearings. And it was during that time that I …
Get the full transcript (3,601 words) + summary by email — free
One-time email with the complete transcript and AI summary of this episode. No account needed.
One email, no spam. We’ll also show you what SignalCast does.
You just read a 3-minute summary of a 21-minute episode.
Get The Daily (NYT) summarized like this every Monday — plus up to 2 more podcasts, free.
Pick Your Podcasts — FreeKeep Reading
More from The Daily (NYT)
Naomi Klein and Astra Taylor Say the End of the World is Now on the Table
Sep 12 · 37 min
Odd Lots
Why AI Might Actually Create More Work for Lawyers
Jul 13
More from The Daily (NYT)
The Lives That 9/11 Keeps Taking
Sep 11 · 37 min
More from The Daily (NYT)
A Couple Breaks Up. Who Gets Custody of Their Embryos?
Sep 10 · 43 min
More from The Daily (NYT)
We summarize every new episode. Want them in your inbox?
Naomi Klein and Astra Taylor Say the End of the World is Now on the Table
The Lives That 9/11 Keeps Taking
A Couple Breaks Up. Who Gets Custody of Their Embryos?
Trump’s War on Mail-In Voting
‘Buy Now, Pay Later’: A New Wave of Consumer Debt
Similar Episodes
Related episodes from other podcasts
Explore Related Topics
This podcast is featured in Best News Podcasts (2026) — ranked and reviewed with AI summaries.
You're clearly into The Daily (NYT).
Every Monday, we deliver AI summaries of the latest episodes from The Daily (NYT) and 192+ other podcasts. Free for one show.
Start My Monday DigestNo credit card · Unsubscribe anytime