Trump Administration Loses Battles Against Big Law Firms

Efforts to punish law firms for representing Trump's perceived enemies hit legal roadblocks.

Published on Mar. 5, 2026

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The Trump administration has faced a series of legal defeats in its attempts to punish major law firms that have represented clients or causes opposed by the president. Despite signing executive orders targeting firms that supported diversity initiatives, represented the Democratic Party, or employed prosecutors who worked on the Mueller investigation, at least four law firms successfully challenged the orders in court, with judges ruling them unconstitutional. However, the administration's efforts to chill dissent and deter law firms from taking on cases against the government appear to have had a chilling effect, with many firms scaling back pro bono work and representation of clients challenging the administration's policies.

Why it matters

The attacks on law firms are part of a broader strategy by the Trump administration to undermine independent sources of power that could challenge the president's agenda. By targeting major institutions like universities, media companies, and law firms, the administration aims to prevent people and organizations from being able to effectively fight back against its policies through the legal system.

The details

In his first months in office, Trump signed executive orders that targeted law firms that supported diversity initiatives, represented the Democratic Party, advocated for liberal causes, or employed prosecutors who had worked on the Mueller investigation. At least nine firms agreed to provide $1 billion in pro bono work for causes agreeable to the president in order to avoid retaliation. However, four firms decided to sue, and over the course of a year, four separate judges ruled the president's executive orders were unconstitutional.

  • In his first months in office, Trump signed the executive orders targeting law firms.
  • Over the course of a year, four separate judges ruled the executive orders unconstitutional.
  • This week, the Department of Justice initially moved to dismiss its appeals in these cases, but then quickly withdrew that motion.

The players

Donald Trump

The former president who signed the executive orders targeting law firms.

Jameel Jaffer

A law professor at Columbia University and the inaugural director of the school's Knight First Amendment Institute, who commented on the Department of Justice's actions as "clown show authoritarianism."

Deborah Pearlstein

The director of Princeton University's Law and Public Policy program, who has been critical of law firms' capitulation to Trump's demands.

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What they’re saying

“Clown show authoritarianism,”

— Jameel Jaffer, law professor at Columbia University and inaugural director of the school's Knight First Amendment Institute (San Francisco Chronicle)

“The concern about the attacks on these Big Law firms is not about protecting Big Law as such. Every single one of these firms, the firms that made deals with the administration and the firms that fought back against the administration, made an enormous amount of money last year. They're doing OK. What's suffering as a result of these attacks: the ability of ordinary people who were on the receiving end of crackdowns to get good representation to fight back.”

— Deborah Pearlstein, director of Princeton University's Law and Public Policy program (Slate)

What’s next

The judge in the case will decide on Tuesday whether or not to allow Walker Reed Quinn out on bail.

The takeaway

This case highlights growing concerns in the community about repeat offenders released on bail, raising questions about bail reform, public safety on SF streets, and if any special laws to govern autonomous vehicles in residential and commercial areas.