The Daily Why One Lawyer Resigned When His Firm Caved to Trump: An Update
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Dec 29, 2025 
In this thought-provoking discussion, Thomas Sipp, a former lawyer at Skadden Arps, shares his journey from a promising legal career to taking a stand against his firm's controversial deal with the Trump administration. He reflects on the moral dilemmas faced by lawyers in the current political climate and reveals the emotional weight of his resignation. Thomas also emphasizes the importance of legal ethics, the courage to speak up, and the complexities of navigating professional loyalty versus personal beliefs.
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Immigrant Childhood Sparked A Legal Calling
- Thomas Sipp describes immigrating from Japan and finding his sense of injustice in school and politics.
- Those experiences led him to debate, political internships, and ultimately law school to pursue justice.
Pro Bono As A Recruiting Differentiator
- Skadden marketed its pro bono program and diversity initiatives as differentiators to recruits like Thomas Sipp.
- Unlimited pro bono hours counting toward billable requirements made the firm attractive to idealistic young lawyers.
When The Firm Entered Trump's Crosshairs
- Thomas recounts the EEOC letter listing 20 firms and the fast-moving negotiations after Paul Weiss's earlier deal.
- He and colleagues felt voiceless as internal threads and news signaled Skadden was negotiating to avert an executive order.