Trump’s September 23 hangover just kept rolling · The Daily Fuckup

Edition · September 24, 2021

Trump’s September 23 hangover just kept rolling

A New York judge kept the pressure on the Trump Organization, while Trump’s Twitter-fight legal theory kept looking more like a tantrum than a case. The day’s biggest Trump-world problems were about paper trails, subpoenas, and the growing gap between his swagger and his filings.

On September 23, 2021, Trump-world took hits on both the business and messaging fronts. In New York, a judge’s order kept the Trump Organization under a hard compliance clock in the state attorney general’s investigation. In federal court, Trump’s separate bid to force Twitter into his preferred legal venue rested on the eye-rolling claim that he should be treated as the 45th president rather than just another litigant. Neither episode was a full-blown knockout by itself, but together they showed the same familiar pattern: Trump’s legal team asking for special treatment, and courts responding by asking for actual paperwork.

Closing take

The day’s Trump story was not a single explosion. It was a drip of institutional skepticism, the kind that turns into something worse only because the paper trail keeps getting longer. That is how a lot of Trump screwups work now: not with one giant collapse, but with a stack of smaller defeats that make the next one easier.

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New York judge keeps Trump Organization on a subpoena leash

Subpoena squeeze Confidence 4/5

★★★★☆Fuckup rating 4/5 Serious fuckup

A New York judge kept the Trump Organization under a September 30 deadline to explain how it was preserving and producing records tied to the state attorney general’s subpoenas. The order did not end the investigation, but it made clear the company was still being dragged through the machinery of a civil fraud probe that has hovered over Trump’s business empire for months. That is not a headline the Trump brand wants anywhere near it.

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Story

Trump’s Twitter case leans on a ridiculous presidential exception theory

Forum-fight flop Confidence 4/5

★★★☆☆Fuckup rating 3/5 Major mess

Trump’s lawyers told a federal court that Twitter’s terms-of-service venue rules should not bind him because he was acting as the 45th president. That is an extraordinary argument for a private-citizen plaintiff to make, and it invited exactly the kind of eye-rolls and skepticism you would expect. The filing exposed how badly Trump’s legal strategy depends on pretending the old title still confers new powers.

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