Associates’ Trump Deal Exits
Ben Thomson, LawFuel contributing editor
In the marble-lined corridors of legal power, a rebellion is brewing over the ‘Trump deals’ being made by biglaw firms targeted by the administration in recent weeks.
Associates at two of America’s most prestigious law firms are doing what many might have thought to have been the unthinkable—resigning from coveted positions that pay north of $220,000 annually to protest their firms’ Faustian bargains with President Trump, marking perhaps the most significant crisis of conscience Big Law has faced in a generation.
The drama unfolding at firms like Paul Weiss and Skadden reveals the fragile ecosystem of modern law firm politics, where rainmaking partners earning $20 million annually have prioritized business continuity over the pro bono principles that once attracted idealistic recruits.
Both firms struck deals with the Trump administration to reverse executive orders that threatened their operations, agreements that required redirecting pro bono resources toward causes favored by the White House while curtailing work that opposes administration policies.
“Skadden is on the wrong side of history,” wrote Thomas Sipp, a 27-year-old Columbia Law graduate, in his resignation letter after less than two years at the firm. “I could no longer stay knowing that someday I would have to explain why I stayed.”
Sipp wrote a rousing email departure ‘speech’ AbovetheLaw’ reported in full saying, in part:
[T]here was a time when I sincerely believed that this place was committed to its true pro bono causes and diversity initiates, even though these thing may to 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?
The firms’ leadership appears unmoved by the internal dissent.
At Paul Weiss, Chairman Brad Karp, (pictured) who was once positioned as a bulwark against Trump’s previous administration, quickly pivoted to negotiation when faced with an executive order, reportedly offering pro bono work on some undoubtedly worthy Trump-endorsed initiatives including a sovereign wealth fund, which Karp explained in his memo to the firm.
Meanwhile, Skadden appears to be actively suppressing dissent, with departing associates reporting they were blocked from widely announcing their resignations via firm email channels.
Recruiting Pipeline Under Threat
The repercussions extend beyond current staff. Georgetown University’s Energy Law Group, with over 150 members, canceled a recruiting event at Skadden’s Washington office, citing the firm’s “pre-emptive acquiescence to pressure from the Trump administration.”
This could create a recruitment crisis for firms that have long traded on both prestige and progressive values in the competition for top law school talent.
In contrast to the capitulation strategy, peer firms including WilmerHale and Jenner & Block have chosen to fight the executive orders in court, positioning themselves as defenders of legal independence.
Paul Weiss has systematically removed web pages highlighting its “leadership in a court-ordered effort to find parents deported by the Trump administration and to reunify families” and scrubbed mentions of pro bono work supporting LGBTQ+ rights—leaving behind only error messages where principle once stood.
For an industry built on precedent, these firms have created a dangerous one. As one former associate who organized a virtual shiva—yes, a mourning period—for Paul Weiss put it, the decisions appear nothing short of “cowardly.”
The true cost of these settlements won’t be measured in billable hours lost but in reputational currency devalued. Time will tell just what that cost may be.
