The ‘Big Law’ Firms That Bowed to Trump and Kissed 💋 His Ring 💍 Lose Clients

May 1, 2025 11:19 PM EDT, Thu

Microsoft drops a law firm that appeased Trump, hires firm that’s fighting Trump

Law firms that struck deals with the [White House thought it’d protect their bottom line. What if their assumptions were wrong?

May 1, 2025, 1:02 PM EDT By Steve Benen

When Donald Trump launched an unprecedented offensive against prominent law firms, the businesses faced a difficult decision. If they appeased the president, they’d (theoretically) avoid White House punishments — penalties that the firms’ clients might have a problem with — but their reputations would suffer.

If, on the other hand, they fought back against Trump’s authoritarian-style assault, they’d preserve their credibility but risk defeats in court and potentially would lose clients that want legal representation with intact security clearances.

To date, four of the targeted firms have chosen the latter course, but they’re in the minority: Most of the targeted firms reached costly deals with the Republican White House.

How’s that working out for all involved?

The president certainly appears delighted, not only because some of the nation’s most important law firms bent the knee, but also because they agreed to hundreds of millions of dollars in free legal services for Trump-aligned causes. The four targeted firms that decided to fight back have reason to be pleased, too, since they’ve scored a series of preliminary legal victories.

As for the firms that went along with the White House’s demands, the news is far less good. Not only are the firms starting to realize that their deals with the president are worse than they first realized, at least one of the firms is also learning that the plan to keep prominent clients happy might be backfiring. The New York Times reported that Microsoft “has dropped a law firm that settled with the administration in favor of one that is fighting it.”

Large companies like Microsoft often farm out legal work to dozens or even hundreds of firms and may move business depending on circumstances, like pricing, expertise or potential conflicts. Microsoft declined to comment on why it changed law firms in a significant case last week, but the switch suggests that a firm that chose to fight the Trump administration could still attract an important client.

While the reporting has not been independently verified by MSNBC or NBC News, the switch has been confirmed in official court filings. About a week ago, attorneys at one firm — Simpson Thacher & Bartlett, which recently reached an agreement with Trump and his team — informed a court in Delaware that it would no longer be representing Microsoft in an acquisitions case.

Instead, the tech giant would be represented by the firm Jenner & Block, which is one of the four firms fighting back against Trump’s offensive.

To be sure, one big company does not a trend make, but given the larger circumstances, it can’t be a reassuring sign to the firms that chose appeasement to see this development unfold.

In the meantime, firms are also contending with a new pressure campaign. NBC News reported last week that a progressive group has launched a media campaign targeting the same firms that have already reached deals with the president.

‘Big law, stop bending the knee,’ reads a poster from the ‘Big Law Cowards’ campaign by the liberal nonprofit group Demand Justice. The group says the ads will be wheatpasted strategically around Washington on Thursday near the locations of the firms that have reached deals with the administration. The group will also have a mobile billboard circulating with ads criticizing the firms, along with a broader digital campaign.

In case this isn’t obvious, the underlying point of these efforts isn’t to chastise the firms for making the wrong decision; it’s to remind the firms that it’s not too late to reverse course and join the ranks of the firms resisting Trump’s gambit.

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