I Know Who Will Go Next in Trump's Reign of Chaos
Oct 18, 2026 · 1h 7m
Summary
Michael Wolff and Joanna Chases analyze the rapid firing of White House press secretary Katie Zachariah, attributing the chaos to Trump’s impulsive hiring and the exclusion of Chief of Staff Susie Wiles. The duo discusses Wiles’ precarious position, her daughter’s rising influence, and the likelihood of her departure after the midterms. They also examine Elon Musk’s unprecedented $300 million spending on the Texas Senate race and its implications for the balance of power. Finally, the hosts review key midterm debates, noting the strong performances of John Ossoff and Abdul Al-Sayed against …
Topics discussed
Sponsorships and Introduction
Susie Wiles' daughter and White House power dynamics
Katie Zachariah's role in the Ukraine war
Weather in L.A. and the Hamptons
Promo for Terragram Ballroom event
Trump's blame game and Zachariah's fate
Trump's fixation on John Ossoff's makeup
Ossoff's debate performance against Susan Collins
Host introductions and background noise
Katie Zachariah's relief after dinner with Vance
The public mockery of Zachariah's firing
Happiness as the remission of pain
Trump's comments on Zachariah's departure
Jason Miller's personal issues and press secretary role
HubSpot CRM Sponsorship
Scott Jennings' credibility and the podium
Speculation on Scott Jennings' appearance
The rapid timeline of Zachariah's appointment
Zachariah's appearance on Sean Hannity
White House use of Fox News and photo analysis
Susie Wiles' birthday and Alaska trip
Susie Wiles' exclusion from hiring decisions
Fashion analysis: Wiles vs. Zachariah's shoes
Trump's preference for blondes and Wiles' role
Life on the tarmac and Wiles' future
HubSpot CRM Sponsorship
The 'body man' and Trump's physical proximity
Trump's image: old man with two young women
Promo for Terragram Ballroom tickets
Trump's public defense of Susie Wiles
Wiles' potential departure after midterms
Trump's control and Zachariah's lack of prep
Trump's resentment of shared authority
Wiles' strategy regarding Elon Musk
Wiles waiting for Musk to self-destruct
Wiles' focus on her own survival
The Chief of Staff role vs. administrative officer
Wiles' background with DeSantis and Rubio
Wiles' revenge campaign against DeSantis
Wiles' lack of ambition for bigger things
Susie Wiles' daughter as a White House power
Elon Musk's $300 million donation to Trump
Doge and Musk's power in the executive branch
Musk's antagonism with cabinet secretaries
Musk's departure and government damage
HubSpot CRM Sponsorship
Musk's investment in Ken Paxton in Texas
The significance of $300 million to Musk
Paxton as the hinge for the Senate
Unprecedented billionaire spending in politics
Money creating its own power
Musk's Starlink role in Ukraine warnings
The rise of the American oligarchy
Trump surrounded by oligarchs at inauguration
Tech industry's expedient political alignment
Musk's absence from the campaign trail
Speculation on Musk's health and flu
Impact of Musk's week off on midterms
Transition to specific Senate races
Troy Jackson's authenticity vs. polish
Trump's unpopularity and candidate dynamics
Jackson's charisma issues in Maine
Al-Sayed vs. Rogers in Michigan
Voting against Trump in difficult races
Al-Sayed's improved standing in Michigan
The two Dan Sullivans in Alaska
Possibility of Democratic wins in key races
Potential for Democrats to win all races
Musk's influence and the Minnesota race
Peggy Flanagan's debate performance
Hosts' drink choices and election night plans
Wolff's retreat from alcohol
Daily Beast studio election night coverage
Washington Post ballroom donor list
Jeff Bezos' interest in the ballroom
Discussion on crispness in reporting
Zachariah's brief tenure and 'Candle in the Wind'
Potential impromptu episode on a flight
Closing thanks to staff and members
Anthropic Sponsorship
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