Edition · June 22, 2021

Trump’s Post-Presidency Disaster Zone, June 22, 2021 Edition

On a day when the Trump family business was already under criminal scrutiny, the broader Trump orbit kept running into the same old problem: the more it fought the facts, the worse the facts looked.

June 22, 2021 brought another reminder that the post-presidency Trump machine was still dragging a trail of legal and political wreckage behind it. The biggest story in the orbit that day was the looming criminal exposure around the Trump Organization’s tax and compensation practices, a case that would soon become a formal indictment and deepen the sense that the company was not just under attack, but under investigation for a long-running scheme. Separate from that, Trump and his allies were still battling the aftereffects of Jan. 6 and the collapse of their claims about the 2020 election, with the legal and reputational bill continuing to rise. This edition focuses on the strongest screwups materially landing or escalating on June 22, 2021, with hindsight kept to a minimum.

Closing take

Trump-world did what it always does when cornered: deny, delay, lawyer up, and hope the story burns out. On June 22, 2021, that strategy was already looking threadbare.

Ranked by how bad the fuckup was

5 stars means maximum fallout. 1 star means a smaller self-own.

Story

Trump Org Tax Probe Hangs Over the Family Business

★★★★☆Fuckup rating 4/5 Serious fuckup

The Manhattan tax investigation into the Trump Organization was closing in, and the company was facing the kind of scrutiny that can turn a private-business mess into a criminal case. The immediate problem was not just legal exposure; it was the public return of a pattern that had dogged Trump for years: employees, perks, compensation, and paperwork all seeming to drift toward fraud allegations whenever investigators looked closely. By June 22, the reporting around the case made clear that the Trump Organization was in a deepening hole, even before the formal charges arrived days later.

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Story

Trump’s Election-Lie Machinery Still Had No Exit Ramp

★★★☆☆Fuckup rating 3/5 Major mess

By June 22, 2021, Trump and his allies were still trapped inside the wreckage of the 2020 election lie, and the fallout kept widening. The concrete problem was that the false claims about the election had already fueled investigations, court cases, and congressional scrutiny, while the evidence supporting the claims remained nonexistent. The political damage was no longer theoretical; it was baked into the way the party, the public, and the legal system were forced to respond to his post-election conduct.

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