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Susie Wiles' Plea Deal with History | The Strategy Session

The White House Chief of Staff’s juicy Vanity Fair interview was a preemptive moral escape hatch — not a confession or a mistake.
  • The Trump administration now operates through internal sabotage and public self-preservation rather than discipline or loyalty.

  • The cruelty on display has become aesthetic as much as political, signaling rot instead of strength.

  • Attacking cultural figures like Rob Reiner fractures a coalition that once rationalized anything.


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Rick, Stuart, and Joe circle the same unsettling conclusion from different angles: this is what a system looks like when everyone knows the ending and starts freelancing their own alibis. Rick’s focus on imagery and power reveals how decay announces itself visually before it collapses institutionally, while Stuart sharpens the moral indictment by treating these moves as intentional acts of historical positioning. Joe keeps returning to how abnormal this is—how no previous White House tolerated this level of self-exposure without consequences—because the abnormality is the point. Together, they sketch a culture that no longer believes in governance, only exits, where cruelty is rewarded, loyalty is transactional, and the final fight is over who gets to say they weren’t really part of it.

Tune in for a conversation that strips away the excuses and asks what responsibility looks like when everyone can see the collapse coming.

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