
Best of the Spectator Americano: is James Comey going to jail?
Sep 29, 2025
Jacob Heilbrunn, Editor of The National Interest, joins Freddy Gray to delve into intriguing facets of U.S. politics. They discuss why Trump is pursuing James Comey and the implications of a Virginia indictment. Jacob explains the significance of court strategy and examines potential cases against figures like John Bolton. The conversation highlights concerns over overclassification in American politics, and the discussion takes a turn toward perceived authoritarianism in Washington. They also explore Trump’s influence on national security and media dynamics.
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Prosecutions As Political Theater
- Using prosecutions as political signals can intimidate opponents without securing convictions.
- Heilbrunn notes this strategy is double-edged and could humiliate Trump if it backfires.
Bolton's Documents Risk
- The case against John Bolton may be stronger because of alleged mishandling of classified documents tied to his memoir.
- Heilbrunn concedes Bolton may have exposed himself to prosecution despite political motives.
The Problem Of Overclassification
- The U.S. wildly overclassifies information, making classification a tool that can be weaponised.
- Heilbrunn links this trend to historical cases and argues classification controversies often obscure deeper issues.


