The Lawyers Who Left Millions to Fight Trump

They had everything — until defending democracy meant losing it all.

Welcome back to The Red Letter.

What happens when the people sworn to defend the rule of law decide they’ve had enough at their high-paying law firms?

That’s the question at the heart of this week’s episode of The Tara Palmeri Show featuring

Matthew Wollin

, a former attorney at WilmerHale, one of the most powerful law firms in America. It’s the same gleaming glass fortress in Manhattan you might recognize from Succession, where he spent five years in their anti-discrimination practice before walking away from a lucrative career to become a journalist.

His breaking point came earlier this year when President Trump issued executive orders targeting major law firms, accusing them of political bias and threatening to strip them of federal contracts. What shocked Wollin wasn’t the attack itself — it was how many of the country’s most prestigious firms folded immediately, rushing to make private deals with Trump rather than fight him in court. Some, even before they were targeted.

“If Trump is surprised at his own success, you know that it really must have been weak ground,” Wollin said. “Because he is not a man who tends to be surprised at his own success.”

Wollin believed that these executive orders were so weak that they would have been easily won. To him, that moment exposed a rot at the top of the legal world. Firms like Kirkland and Ellis and Wilkie Farr quietly agreed to “settlements” so vague that even Congress couldn’t get details, with firms telling lawmakers to check Trump’s Truth Social account for the terms of the deal. Another pointed to an internal email reported in a trade journal behind a paywall. For an industry that fetishizes fine print, it was surreal that they didn’t appear to have a contract with the administration. As Wollin put it, “pretty bad lawyering.”

A Crisis of Conscience Inside Big Law

Wollin describes the atmosphere inside Big Law as a paradox: places that preach neutrality while functioning like corporate fortresses with deep ideological roots — Jones Day leaning right, WilmerHale left. For decades, lawyers told themselves they were above politics. But when Trump turned his legal ire on them, neutrality collapsed.

Some lawyers quietly left. Others went public. A few, like Wollin, started over entirely, watching the defenders of democracy cave under attack.

In their wake, a small resistance movement is forming. There are a handful of new boutique firms and nonprofits that see themselves as defenders of the rule of law. Legal power house Abbe Lowell, who once represented Jared Kushner and Hunter Biden, started his own practice and scooped up associates who quit Skadden Arps in protest. These rule of law startups are taking the cases the establishment firms won’t touch.

The Human Cost of Conscience

For every lawyer who left, hundreds stayed often citing the same reasons most of us stay anywhere: comfort, family, fear. “Quitting a normal job for normal reasons is also already a big disruption to your life and takes a lot,” he said.

He’s not wrong. Partners have kids in private school, mortgages, and dinner parties with the very people running the administration they’re supposed to hold accountable. Leaving means exile, and for many, that’s unthinkable.

But the few who did walk away have become the conscience of a profession that’s supposed to guard democracy, not negotiate its terms.

If lawyers are trained to believe they’re the immune system of American democracy, what happens when the immune system gives up?