What happens when you realize you don’t belong at your law firm
If you haven’t listened to this morning’s NYT The Daily podcast, please do: https://www.nytimes.com/2025/04/07/podcasts/the-daily/skadden-lawyer-resigned-trump-thomas-sipp.html. Thomas Sipp explains why he’s resigned from his law firm, Skadden, Arps, Slate, Meagher & Flom LLP.
Sipp is the son of a white American father and a Japanese mother. At age 10 he moved with his family from Japan to the United States. His childhood struggles to speak English, amidst classmate bullying, are a testament to his hard work and dedication. His early interest in history was the foundation for his admiration for America and the opportunities it offers. At Columbia Law School, saddled with six-figure student debt, he found Big Law a practical career choice, and Skadden a good choice because of its excellence and also the firm’s commitments to diversity and to meaningful pro bono work. And by all accounts, Sipp worked hard. Picking an apartment five minutes from the firm allowed him each day to arrive at work early, and to stay late.
But Sipp’s belief in his law firm was shaken, and ultimately broken, by Skadden cutting a deal with the Administration to avoid a punitive Executive Order. I’ll leave it to Sipp to describe what unfolded.
In his resignation email, Sipp states:
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.
I am sure some of you will question my decision and chalk it up to me being a young attorney too eager to throw his career away. I am sure there will also be those of you who will think of me as naïve. But there was a time when I sincerely believed that this place was committed to its true pro bono causes and diversity initiatives, even though these things may not always be lucrative, because it believed these things would make the world, and this firm, a better place. Having held itself out as a champion for these values, for this firm to turn its back on them so suddenly and so easily was shameful. I am embarrassed to work here. How can Skadden represent others when it can’t even stand up for itself?
* * *
I am making this decision to leave even though I was happy here. I have made so many great friends at this firm and learned from many great mentors. Thank you so much. I will miss you all dearly. And I am making this decision knowing that not everyone can leave as readily as I can, that many of you have families who depend on the income you earn here – I do not mean to shame you into leaving, only to explain my decision.
Skadden is on the wrong side of history. I could no longer stay knowing that someday I would have to explain why I stayed.
As a parent, what really got to me in his Daily interview was when Sipp recounted his phone conversation with his Mom, who now lives in Japan. She became very quiet on the call as his decision to resign sank in. Her first question was whether he had a new job (we parents are so predictable). Her next question was whether he’ll leave America and return to Japan. Sipp is an emphatic no on that – he clearly believes he belongs here, simply not at Skadden.
In the recruiting section of Skadden’s website, under “Carve Your Own Path,” one can still see (at least as of today), the following from a Skadden partner:
Best career advice I’ve received
To be true to myself and stick up for what I believe in. Recognizing that doing so may have unforeseen consequences, I take to heart that remaining honest and being respectful tend to yield positive results. It sometimes can be difficult to speak up, especially with a judge, a client or a more senior lawyer, but this advice helps me to stand up for things that are important to me.
Looks like Sipp believed in what Skadden says on its recruiting website, at least until it collided with the reality of what the firm does when faced with a brutal choice.
Sipp says that entering into this agreement with the Administration “changed” what the firm stands for. With utmost respect, I believe these moments are more about revealing than changing – it reveals what the firm actually stands for, when everything is on the line. And yes, I know it’s easy for me to glibly judge, without existential repercussions at stake.
We reveal who and what we are through our actions, not our words. Status, prestige, and money are of course powerful inducements to stay at a law firm. But lest we forget, so is Belonging.