The Daily (NYT) – Episode Summary

Title: Why One Lawyer Resigned When His Firm Caved to Trump: An Update
Date: December 29, 2025
Host: Michael Barbaro
Guest: Thomas Sipping (former Skadden, Arps associate; now federal law clerk)

Overview

This episode revisits the story of Thomas Sipping, a young lawyer who resigned from the prestigious firm Skadden, Arps after it capitulated to Trump administration demands regarding its diversity practices. Eight months later, Thomas reflects on his decision, the fallout, and where it’s taken him, providing insight into the ethical crucible facing the legal profession in the Trump era and how principled stands can shape both personal and professional futures.

Key Discussion Points & Insights

1. Thomas’s Background and Motivation for Law (00:59–05:42)

• Thomas recounts immigrating from Japan as a child, navigating English and American identity, and developing a keen sense of justice born from his experiences as a racial minority and a child of a single, non-English-speaking mother.
• His idealism stemmed from America’s “march towards justice” and aspirations toward universal opportunity.
• He describes joining law to be part of “this project” in America (03:32), ultimately drawn to Skadden for its prestige, pro bono programs, and commitment to diversity.

Quote:
“It’s, you know, 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.”
— Thomas Sipping (03:32)

2. Skadden, Arps and Trump’s EEOC Orders (05:42–08:18)

• On March 17, the EEOC lists 20 major law firms, including Skadden, as being under investigation for their diversity, equity, and inclusion (DEI) programs—implying possible discrimination for such initiatives.
• Peer firms like Paul Weiss struck deals with the administration involving multimillion-dollar pro bono commitments to causes the President favored.
• Momentum in Skadden among associates to resist the order was stymied by how quickly the firm leadership moved to make a deal, leaving young lawyers feeling voiceless.

Quote:
“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, but we’re feeling like things are moving really fast, and we felt voiceless.”
— Thomas Sipping (07:26)

3. The Content of the Deal—And Thomas’s Reaction (10:05–12:14)

• Skadden agrees to provide $100 million in pro bono legal services to explicitly Trump-approved causes, hire conservative-minded “Skadden Fellows,” and avoid “illegal DEI hiring practices.”
• Thomas is shocked and ashamed, feeling the firm’s prestige is permanently tainted and that it’s complicit in constitutional harm.

Quote:
“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...to see Skadden be complicit...I was so ashamed to work there.”
— Thomas Sipping (12:03)

4. Thomas’s Resignation Letter and Decision Process (12:16–15:08)

• What began as questions about the deal evolved into a resignation letter, which Thomas reads aloud.
• He frames his decision in the context of historical moments of courage or complacency: “What would I do if I was there? Would I do the right thing?” (13:23).

Quote:
“Scadden’s agreement with the Trump administration sent our country deeper down this descent. 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.”
— Thomas Sipping (14:08)

• Sending the email felt “like that [deep breath] maybe a hundred times more”—a pivotal moment with great risk and uncertainty.

5. Family and Practical Consequences (15:25–17:01)

• Thomas describes the emotional conversation with his mother, who is fearful for his job prospects and safety, and the broader risks of taking public stands.
• Barbaro raises the perspective of firm leaders claiming the deal doesn’t change the firm’s identity, which Thomas curtly rebukes.

Quote:
“I just don’t think that’s true. These law firms are agreeing to these deals when they know there’s no legal basis for any threatened executive order. And by capitulating, they’re aiding this existential threat against the profession, the independence of the judiciary and our democracy.”
— Thomas Sipping (17:01)

6. Reflections on the Profession and Country (17:32–19:16)

• Despite worry and fear, Thomas remains hopeful that collective pushback can still preserve American democratic values.
• He does not regret entering the law, stating: “It’s a wonderful education...equipping me with skills...to advocate for what I believe in and for others as well, and that’s what lawyers do.” (18:46)

7. Eight Months Later: What Happened Next? (21:00–25:24)

• After going public, Thomas receives an outpouring of support—including from parents and their kids, using his story as a teachable moment.
• He lands a clerkship for a federal judge, found through intersecting networks—not by seeking, but “the judge actually found me.”
• While unable to discuss case details, he emphasizes that both he and his judge operate according to legal and ethical standards—not as partisan actors.

Quote:
“And I think the true interpretation is that I made this decision on ethics grounds, and it was about what I thought 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. Say I was fine. I was actually more than fine.”
— Thomas Sipping (24:06)

• He addresses the legal profession, encouraging lawyers to find courage: “Not everyone in America can safely speak their mind right now. But lawyers can...the law firms that fought back and are winning in courts are doing fine financially...that existential fear was completely overblown.” (24:48–25:26)

Notable Quotes & Memorable Moments

• “Scadden is on the wrong side of history. I could no longer stay, knowing that someday I would have to explain why I stayed.” (14:08, Thomas Sipping)
• “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...would have been completely fine too. And regardless, I think the oaths have to mean something.” (25:26, Thomas Sipping)
• “There is another side to quitting a big, prestigious, well-paying job at a law firm on principle. In the year 2025, you’ll end up all right.” (24:44, Michael Barbaro and Thomas Sipping)

Important Timestamps

• Introduction & Thomas’s Background: 00:48–05:42
• The EEOC Letter & Law Firm Response: 05:42–08:18
• Skadden’s Deal With Trump: 10:05–12:14
• Thomas’s Resignation Decision & Letter: 12:16–15:08
• Family Reaction & Broader Consequences: 15:25–17:01
• Reflection on the Profession & National Future: 17:32–19:16
• Update—Life After Resignation: 21:00–25:26
• Closing Remarks: 26:01

Overall Tone & Takeaways

The episode is a candid, idealistic, and at times poignant exploration of personal ethics versus institutional pragmatism, the power of principle even in high-stakes environments, and the ways individual acts of conscience can ripple outward. Thomas Sipping’s story offers hope to those feeling pressure to compromise, demonstrating that integrity can, and often does, find its own reward.