Story
Trump Loses Bid to Halt New York Attorney General Probe
On May 27, 2022, a federal judge dismissed Donald Trump’s lawsuit seeking to block New York Attorney General Letitia James’s investigation, clearing the way for it to continue.
Edition · May 27, 2022
The Daily Fuckup: May 27, 2022
A backfill edition on the strongest Trump-world screwups that landed on May 27, 2022, with a sharp eye on legal blowback, money trouble, and the kind of optics that keep turning into liabilities.
On May 27, 2022, the Trump universe was still dealing with the same recurring problem: when the story is about the business, the money, or the lawyers, it is almost never a good sign. The best-documented material for the day is thinner than a full-speed scandal cycle, but there were still meaningful signs of pressure around Trump-linked legal exposure and the increasingly messy overlap between politics, private enterprise, and public scrutiny. This edition focuses on the most substantive, best-supported screwups that were in motion or materially visible on that date.
Closing take
It was not a day with a single giant Trump-world explosion. But it was very much a day when the underlying pattern stayed ugly: the legal, financial, and political problems were not fading, and the people around Trump kept finding new ways to remind everyone why that machine always seems to be on fire.
Ranked by how bad the fuckup was
5 stars means maximum fallout. 1 star means a smaller self-own.
Story
Truth Social’s SPAC Deal Was Drawing Fresh Scrutiny in May 2022
By May 27, 2022, the Truth Social merger with Digital World Acquisition Corp. was still alive, but it was already under pressure from a federal probe and repeated disclosure questions. The hard fact for that date is narrower than later headlines would suggest: the deal had been amended on May 11, and the broader SEC fraud finding came more than a year later.