Microsoft routinely farms out its legal work to third-party firms. It’s a standard practice—hire the best lawyers for the job, keep things running smoothly, and avoid unnecessary headaches. But Microsoft’s latest move suggests that sometimes, the choice of legal counsel isn’t just about expertise—it’s about politics.
Simpson Thacher & Bartlett, a powerhouse in corporate law, recently struck a $125 million pro bono deal with the Trump administration. On paper, the agreement was framed as a commitment to serving “underserved populations.” In reality, critics argue that it was a strategic move to shield the firm from Trump’s executive orders, which have targeted law firms over diversity and hiring practices.
The deal wasn’t unique—several elite law firms have made similar arrangements, pledging massive amounts of free legal services to avoid retaliation from the administration. The fear? That non-compliance could trigger punitive executive orders, investigations, or even loss of lucrative government contracts.
While Microsoft hasn’t explicitly stated why it dropped Simpson Thacher, the timing speaks volumes. The tech giant quietly replaced the firm with Jenner & Block, a law firm that is actively suing the Trump administration over executive orders that restrict legal industry access and security clearances.
Jenner & Block has taken a hard stance against Trump’s legal maneuvers, calling his executive orders an “unconstitutional abuse of power”. The firm argues that the administration’s actions are designed to punish law firms that have represented clients opposing Trump’s policies.
Microsoft’s decision to swap law firms could be seen as a conflict of interest—why keep a firm that’s cozying up to an administration that has repeatedly clashed with Big Tech? Alternatively, it could be a purely financial decision. If Simpson Thacher is aligning itself with Trump’s agenda, Microsoft may see no benefit in maintaining the relationship.
After all, Microsoft has historically maintained bipartisan relationships and a low political profile. But in today’s climate, even neutrality comes with risks. The company may have decided that sticking with a firm perceived as capitulating to Trump was more trouble than it was worth.
Microsoft’s move signals a shift in how major corporations weigh political risk. For months, law firms feared losing business by standing up to the Trump administration. But now, it seems companies are more concerned about being associated with firms that have aligned themselves with Trump.
This isn’t just about Microsoft—it’s about the broader legal industry. Firms that compromise their independence to appease political forces may find themselves losing high-profile clients. Meanwhile, firms that fight back could see their reputations—and their client lists—grow stronger.
Microsoft’s decision may not be the last of its kind. As the legal world continues to navigate political crosscurrents, expect more corporations to rethink their legal alliances—and maybe even start picking sides. Especially in light of executive orders and tariff wars that inversely affect their bottom line.
Game on.
