Edition · May 29, 2025
Trump’s May 29 mess: tariffs wobble, the courts bite, and the grift keeps dripping
A backfill edition for May 29, 2025, on the day Trump world kept discovering that “move fast and break things” is not a legal theory, a trade policy, or an ethics plan.
May 29 was one of those days when the Trump operation managed to look both overpowered and fragile at the same time. The biggest headline was the tariff fight: a federal appeals court let the administration keep collecting duties, but only while the broader legal mess kept grinding forward. On the same date, the White House was still signaling that Trump’s family business would keep opening the door to private foreign deals, a self-inflicted ethics problem that undercuts the whole “drain the swamp” act. The result was a familiar Trump-world combo platter: public toughness on the outside, legal uncertainty and conflict-of-interest stink on the inside.
Closing take
The through line here is simple: Trump world keeps trying to govern by improvisation, and the courts, the markets, and basic ethics keep throwing back the receipt. May 29, 2025 was not a day of one catastrophic collapse, but it was a very good illustration of the cumulative damage caused when the same crew treats every guardrail as optional.
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Tariff limbo
Confidence 5/5
★★★★☆Fuckup rating 4/5
Serious fuckup
The Federal Circuit on May 29 issued an administrative stay that temporarily paused the Court of International Trade’s judgments and permanent injunctions in the tariff cases. It did not rule on whether the tariffs are lawful.
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Foreign deal risk
Confidence 5/5
★★★☆☆Fuckup rating 3/5
Major mess
The Trump Organization’s January 10, 2025 ethics plan bars direct deals with foreign governments but still permits private foreign-company deals, a break from the tighter first-term pledge. The structure keeps conflict-of-interest concerns alive because it leaves open a channel for foreign money while Donald Trump is back in office.
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Law-firm pressure campaign
Confidence 4/5
★★★☆☆Fuckup rating 3/5
Major mess
By May 29, the administration was still pressing a spring campaign against major law firms, after White House actions on Perkins Coie on March 6, Jenner & Block on March 25, and WilmerHale on March 27.
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