The Daily Beast Podcast These Are Trump's Biggest Achilles' Heels: Wolff
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Jan 21, 2026 
Michael Wolff, a seasoned journalist known for his insider insights into the Trump presidency, dissects the pervasive myth of Trump as a mastermind strategist. He argues that Trump's dominance stems from a performance-driven persona rather than calculated strategy. They explore key vulnerabilities, including the economy and immigration issues, while also highlighting how Trump's impulsive social media posts often shape policy. Wolff also critiques the transactional nature of Trump's diplomacy, exposing a potential grift tied to family profits.
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Policy Via Middle-Of-Night Posts
- Trump often announces policy impulsively from his phone and Truth Social.
- Wolff says White House staff wake to his posts and scramble to make them into policy.
The Mirror Effect Of Outrageous Claims
- Trump's off-the-cuff pronouncements force others to treat unserious ideas as real.
- Wolff notes this dynamic makes him begin to believe his own impulsive policies like 'Greenland.'
Greenland's Real Cost And No Gain
- Trump's Greenland gambit creates diplomatic and economic risks with no clear benefit.
- Wolff highlights that the move undermines NATO and forces allies to take it seriously despite its incoherence.
