President Donald Trump reacts, as he attends a ceremony held to dedicate a 4-mile stretch of road from West Palm Beach Airport to his Mar-a-Lago estate as "President Donald J. Trump Boulevard," at the Mar-a-Lago estate in Palm Beach, Florida on Jan. 16, 2026. REUTERS/Kevin Lamarque
President Donald Trump’s administration has humbled some of the largest law firms and highest-paid individuals in the legal profession. And other businesses and individuals that potentially need his grace on their activities have to be watching and wondering if they are next.
That’s the conclusion of a New York Times opinion piece by contributor Jeffrey Toobin, which notes that bullies (i.e., the Trump administration) “are never satisfied with just a single capitulation.”
The lesson to be drawn is that government pressure is effective even when its actions are clearly unconstitutional.
What the opinion piece terms “nonstop chaos” caused by the Trump administration began last year with executive orders targeting progressive law firms that worked for Trump opponents and causes he doesn’t favor. The orders would have created insurmountable barriers to the law firms' corporate activities.
Some of the firms in the cross hairs of those orders opted to settle by offering the administration millions in pro-Bono legal work on favored causes.
Last year, four judges ruled that the executive orders targeting the law firms were unconstitutional. The Department of Justice appealed, but then decided earlier this month that it was dropping the plans.
The next day, the appeals were placed back on.
“The about-face was embarrassing, but it obscured a larger truth of this lamentable episode: President Trump had already won this fight months ago, when the American legal profession — especially its largest and richest law firms — lost. And that’s not funny at all.”
While the legal profession was initially targeted, there’s a broader application underway. The Trump administration has presented the same “extortionate choices” to a variety of targets, including universities and companies.
The implication of the administration's message is clear: “Agree to our unconstitutional demands and sacrifice your principles, or fight back and suffer our wrath in the form of lost patronage and dollars.”
In all of those cases, Toobin argues, “surrender looks — and perhaps even is — the path of least resistance.” But giving in may embolden further actions, “and you don’t have to be a lawyer to see that was a foolish choice indeed.”
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