Edition · May 27, 2025

Trump’s war on the press and the bar keeps getting litigated into the ground

On May 27, 2025, Trump-world racked up two clean, document-driven setbacks: NPR sued over the White House’s public-media defunding order, and a federal judge tossed another one of the administration’s attacks on a major law firm.

May 27 was a bad day for the White House’s revenge-via-executive-order hobby. In Washington, NPR and three member stations sued over Trump’s attempt to choke off federal support to public media. In a separate ruling, a federal judge struck down Trump’s executive order targeting WilmerHale, adding another judicial body blow to the administration’s campaign against law firms it considers disloyal. Together, the two episodes underline the same problem: Trump keeps using the government like a personal grievance machine, and the courts keep reminding him that the Constitution is not optional.

Closing take

The through-line is ugly and familiar: when Trump loses patience with institutions that irritate him, he reaches for punishment, not policy. On May 27, that instinct produced another pair of legal setbacks that looked less like governing than like a very expensive tantrum. The optics are bad, the law is worse, and the pattern is getting harder for even friendly lawyers to defend.

Ranked by how bad the fuckup was

5 stars means maximum fallout. 1 star means a smaller self-own.

Story

Judge knocks down Trump’s latest law-firm vendetta

★★★★☆Fuckup rating 4/5 Serious fuckup

A federal judge struck down Trump’s executive order targeting WilmerHale, calling it unconstitutional and adding another humiliating courtroom loss to the administration’s campaign against law firms it dislikes. The ruling deepens the sense that Trump is using government power to settle private scores — and that the courts are done entertaining the stunt.

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Story

NPR drags Trump to court over his public-media defunding order

★★★★☆Fuckup rating 4/5 Serious fuckup

NPR and three member stations sued the Trump administration after the White House ordered federal support for public broadcasting to be cut off, calling it unconstitutional retaliation for news coverage Trump dislikes. The lawsuit turns the administration’s latest media attack into a first-amendment and separation-of-powers fight that could become a bigger test of how far the White House can go in punishing disfavored speech.

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