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.
Story
Tariff limbo
Confidence 5/5
★★★★☆Fuckup rating 4/5
Serious fuckup
A federal appeals court let the administration keep collecting tariffs under emergency powers while the bigger legal fight over Trump’s signature trade agenda stayed alive. That was a tactical win, but it also underscored how much of the tariff program was still hanging on by courtroom thread. The policy remained tied up in litigation, and the uncertainty itself kept landing real economic and political damage.
Open story + comments
Story
Foreign deal risk
Confidence 4/5
★★★☆☆Fuckup rating 3/5
Major mess
The Trump Organization’s 2025 ethics posture still left room for private foreign deals, breaking with the stricter promise the family business made in the first term. That is an open invitation to influence-seeking and a gift to anyone trying to buy access without ever stepping foot in the West Wing. On a day when Trump-world wanted to project toughness and control, the business side kept reminding everyone that the old conflict-of-interest playbook is still very much alive.
Open story + comments
Story
Law-firm warfare
Confidence 3/5
★★★☆☆Fuckup rating 3/5
Major mess
The administration was still pushing its campaign against major law firms, treating adversarial lawyers as political enemies rather than participants in the legal system. That kind of pressure campaign may thrill the base, but it also sharpens the perception that Trump wants a government built around loyalty tests and retaliation. Even when no single order lands that day, the broader campaign keeps compounding the reputational damage.
Open story + comments
