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As the political landscape increasingly entangles with the legal profession, Biglaw firms are making unprecedented choices—some with dire consequences. One of the most striking developments of 2025 is Microsoft’s decision to drop Simpson Thacher & Bartlett from a major antitrust case, replacing the firm with Jenner & Block, a firm currently in active litigation against the Trump administration.
This move sends a powerful message about where sophisticated corporate clients stand when it comes to law firm alliances with controversial political forces.
The Rise—and Rapid Fall—of the Trump-Biglaw Pro Bono Deals
Earlier this year, several elite law firms, including Simpson Thacher, struck deals with the Trump administration pledging hundreds of millions in pro bono services. The stated purpose? To serve “a wide range of underserved populations.”
In reality, critics warned that this pro bono commitment could end up aligning firms with the administration’s efforts to provide legal defenses for police departments, corporations facing civil rights lawsuits, and other entities aligned with Trump’s agenda.
Why Firms Made the Deal:
- Fear of Retaliation: Firms believed non-compliance could trigger punitive executive orders or targeted investigations.
- Client Retention Concerns: Leaders feared clients might abandon firms under political attack.
- Damage Control: Some hoped to minimize political risks while maintaining a semblance of social responsibility.
But the gamble has backfired—at least for Simpson Thacher.
Microsoft’s Landmark Decision: Firing Simpson, Hiring Jenner
According to The New York Times, Simpson Thacher attorneys officially informed the Delaware Court of Chancery on April 22 that they would no longer represent Microsoft in litigation related to its 2023 acquisition of Activision Blizzard.
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That same day, Microsoft handed the case to Jenner & Block—a firm that has publicly defied the Trump administration and is actively suing to block an executive order targeting its business.
Key Facts:
- Simpson Thacher’s Pro Bono Deal: $125 million in legal work aligned with Trump administration causes.
- Microsoft’s New Choice: Jenner & Block, a firm battling Trump’s policies head-on.
The Broader Implications for Biglaw and Corporate America
Microsoft’s decision is not merely a matter of switching counsel. It’s a seismic public signal:
- Clients Are Watching: Sophisticated corporations are aware of the reputational risks tied to law firms perceived as capitulating to authoritarian pressure.
- Firms That Fight Win Loyalty: Jenner’s willingness to challenge unlawful or unethical executive orders appears to have enhanced its standing with clients who value resilience over appeasement.
- Talent Flight Risks: Firms surrendering to political pressure face not just client loss but also potential attrition as attorneys leave for firms with stronger principles.
Why Microsoft’s Move Matters:
✅ It breaks the narrative that clients prefer firms making “peace deals” with the administration.
✅ It rewards firms that resist political coercion.
✅ It may inspire other corporate clients to reconsider relationships with law firms tied to controversial pro bono commitments.
Silence Speaks Volumes
None of the parties involved—Microsoft, Simpson Thacher, or Jenner & Block—have publicly commented on the switch.
But the facts are impossible to ignore:
- Microsoft could have quietly supplemented its legal team rather than fully replacing Simpson.
- Choosing Jenner, out of dozens of possible alternatives, was a deliberate and conspicuous decision.
In today’s polarized legal landscape, such moves are never just “routine.”
What Comes Next for Biglaw?
Simpson Thacher’s situation may be only the beginning. Other firms that aligned with the Trump administration could face similar fallout:
- Client Defections: More corporations may drop firms involved in politically charged pro bono deals.
- Reputational Risk: Firms may suffer public backlash and diminished appeal among both clients and recruits.
- Market Realignment: Firms standing firm against authoritarian pressures may gain a competitive edge.
As 2025 progresses, Biglaw’s uneasy entanglement with the Trump administration will likely yield further high-profile consequences.
Conclusion: The Cost of Capitulation
When Simpson Thacher and other firms agreed to pro bono deals aimed at placating the Trump administration, they likely believed they were protecting their business interests. Instead, at least in Simpson’s case, the strategy has alienated major clients and sparked a reputational crisis.
Microsoft’s choice to pivot to Jenner & Block reflects a broader trend: In today’s climate, clients want legal counsel that will fight for what’s right—not firms that fold under pressure.
