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Inside the Florida Gamble Behind Jack Smith’s Mar-a-Lago Prosecution Collapse

New reporting describes intense internal warnings about filing in Florida, with a revised estimate showing a much higher chance of drawing Judge Aileen Cannon.

Overview

  • Special counsel Jack Smith opted to charge in Florida on venue grounds after internal analysis that he and Attorney General Merrick Garland believed favored that forum.
  • Career prosecutors, including David Raskin, strongly objected, warning the move was a risky bet given Judge Aileen Cannon’s prior handling of the investigation.
  • The team’s initial 1-in-6 estimate of drawing Cannon was later recalculated to nearly 1-in-3 after factoring judges’ caseloads and availability in the Southern District of Florida.
  • Judge Cannon dismissed the case on July 15, 2024, ruling Smith was unlawfully appointed; Solicitor General Elizabeth Prelogar approved an appeal but rejected a bid to seek Cannon’s removal.
  • Following Trump’s 2024 victory, DOJ policy against prosecuting a sitting president led to abandoning further prosecution; the new details come from Washington Post excerpts of the book Injustice published Oct. 27, 2025.