Edition · May 16, 2026
Trump’s week of forced-fight governance keeps colliding with the courts
A fresh round of lawsuits and appeals shows the administration turning every policy dispute into a constitutional cage match—and not always winning.
Trump-world spent the week leaning on the federal courts to enforce its agenda, from immigration crackdowns to retaliation against law firms and state governments. Some of those moves may still pay off eventually, but the immediate picture is a government that keeps choosing hardball, then discovering the Constitution has its own opinion.
Closing take
The through line here is simple: this White House keeps mistaking aggression for leverage. Sometimes it works long enough to make a splash; increasingly, it also produces filings, injunctions, and the kind of legal bills that never fit on a victory lap.
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Denaturalization enforcement
Confidence 5/5
★★★★☆Fuckup rating 4/5
Serious fuckup
The Justice Department said on May 8 it filed civil denaturalization actions against 12 people, alleging they concealed terrorist ties, war crimes, espionage, sexual abuse and other material facts during the naturalization process.
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Federal supremacy
Confidence 5/5
★★★★☆Fuckup rating 4/5
Serious fuckup
The Justice Department filed suit May 15 challenging Connecticut’s law as applied to federal officers; Gov. Ned Lamont signed the measure May 4 and it became Public Act 26-14 on May 5.
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Law-firm retaliation
Confidence 5/5
★★★★☆Fuckup rating 4/5
Serious fuckup
The D.C. Circuit heard oral arguments May 14 in a consolidated appeal over Trump-era orders and related actions targeting several law firms and lawyer Mark Zaid. The district court blocks remain in place unless the appeals court changes them.
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Tariff backlash
Confidence 5/5
★★★★☆Fuckup rating 4/5
Serious fuckup
A federal trade court’s May 7 ruling knocked down Trump’s 10% global Section 122 tariff as unlawful, undercutting the administration’s fallback plan after its earlier tariff authority was blocked, even though the case is still on appeal.
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Law-firm retaliation
Confidence 5/5
★★★★☆Fuckup rating 4/5
Serious fuckup
The D.C. Circuit heard oral arguments on May 14 in the Perkins Coie challenge to Trump-era executive orders, along with a related Mark Zaid case, and did not announce a decision from the bench.
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Sanctuary crackdown
Confidence 5/5
★★★☆☆Fuckup rating 3/5
Major mess
The Justice Department filed a complaint on April 13, 2026, accusing Connecticut, New Haven and several top state and city officials of blocking federal immigration enforcement.
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Immigration squeeze
Confidence 5/5
★★★☆☆Fuckup rating 3/5
Major mess
The Trump Justice Department filed suit May 8 against New Mexico, Albuquerque and their leaders over local rules limiting immigration cooperation and protecting sensitive public spaces.
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Bar discipline fight
Confidence 5/5
★★☆☆☆Fuckup rating 2/5
Noticeable stumble
The Justice Department filed a complaint on May 13 against D.C. disciplinary authorities, seeking to block bar proceedings tied to Jeffrey Clark and the Trump administration’s anti-‘weaponization’ push.
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Law-firm retaliation
Confidence 5/5
★★☆☆☆Fuckup rating 2/5
Noticeable stumble
The D.C. Circuit heard oral argument May 14 in the Perkins Coie appeal and a separate Mark Zaid appeal. The panel did not announce a ruling that day, so the district-court injunctions stayed in effect for now.
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