Michael Wolff and Joanna Coles look inside a White House bracing for the midterms, where losing the House may be expected but losing the Senate could put nearly everyone around Trump in danger. Wolff describes how election night could unfold inside the residence, why Susie Wiles and Attorney General Todd Blanche may be especially exposed and why Natalie Harp appears to be the one aide whose job is safe. Then he and Coles make their calls on eight Senate races, including the strange contest in Alaska where two men named Dan Sullivan are on the ballot. They also consider whom Trump would blame for a defeat and why his fixation on other people’s looks reveals so much about how he sees himself.

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Michael Wolff and Joanna Coles debate whether Democrats can take the Senate as the midterms approach, with Wolff predicting a sweeping defeat for Trump and Coles warning that Republican money could still make the difference. They turn to a new House Judiciary Democrats’ report on Trump’s relationship with Jeffrey Epstein, including allegations about their ties to the modeling industry, and ask whether the story will finally affect voters. Wolff also discusses Princes and Thieves, a new book about Jared Kushner’s dealings with Persian Gulf leaders, and says its author contacted him after Kushner threatened legal action. From Elon Musk’s election spending to the money flowing through Trump’s family, they trace what a Democratic Congress might investigate.

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Read the House Judiciary Democrats' staff report here: https://democrats-judiciary.house.gov/sites/evo-subsites/democrats-judiciary.house.gov/files/evo-media-document/2026-10.hjc-dems-staff-report-epstein-and-trump.pdf

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Michael Wolff and Joanna Coles look at the Republicans’ desperate final stretch before the midterms, starting with a campaign ad so cruel that even members of their own party are recoiling. Why are Donald Trump and JD Vance standing by Vivek Ramaswamy as his attack on Ohio rival Amy Acton backfires? Wolff explains what the uproar reveals about Trump’s faith in a tactic that has worked for him before, while a ballot fight in Alaska raises fresh questions about how far his administration will go to contest a loss. They also turn to Melania Trump’s claim of a humanitarian breakthrough in Ukraine as her husband moves closer to Vladimir Putin, the Republicans beginning to break with Trump over Russia and new allegations involving his former lawyer Alina Habba. #ad Ready to reach your goals? Visit https://hims.com/ith

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In this special live show edition of Inside Trump's Head, Michael Wolff and Joanna Coles take the stage in Los Angeles to ask what Trump wants from the presidency and what he might do if Democrats win the midterms. Wolff shares what a source close to Trump told him about the president’s staggering financial ambitions, then explains why he believes money drives Trump’s fixation on Vladimir Putin. He and Coles consider how Trump could react to an election defeat, whether he might return to bombing Iran and why Wolff doubts JD Vance can inherit the MAGA movement. The audience brings questions of its own, prompting Wolff to discuss his legal fight with Melania Trump and the unusual place Natalie Harp holds in the president’s inner circle.

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Michael Wolff and Joanna Coles look ahead to the morning after the midterms and ask what happens if Donald Trump loses control of Congress. Wolff, who watched Trump’s inner circle confront him with the 2020 results, explains why he believes the president cannot accept a loss and how a defeat could become an excuse to blame Susie Wiles, Mike Johnson and Republicans who kept their distance from him. Coles presses Wolff on a closer, messier result: Could recounts and challenges leave the country in weeks of chaos? They also imagine who will be at Trump’s side as the returns come in, whether he could still surprise his opponents at the ballot box and why Wolff expects him to fight for the spotlight even if Democrats win.

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Michael Wolff and Joanna Coles go inside the chaos of Trump’s White House, where a disastrous press secretary debut, a sudden firing, and Susie Wiles’ uncertain future expose a West Wing running on ego, loyalty, and dysfunction. As Trump’s revolving door of female aides keeps spinning, Wolff explains why even his own chief of staff may be on borrowed time. Plus, Elon Musk is pouring another $300 million into the midterms, raising the stakes in a series of nail-biting Senate races and giving one billionaire extraordinary power over American democracy. With control of Congress hanging in the balance, Wolff and Coles examine the money, the power plays, and the political consequences that could reshape Trump’s presidency.

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Michael Wolff and Joanna Coles ask whether Susie Wiles is running out of time as Trump reportedly calls around to ask what people think of his chief of staff. Wolff explains why that question can be the kiss of death inside Trump’s White House and predicts what could happen after the midterms. They also take on new press secretary Katie Zacharia’s rocky debut and the questions surrounding her claims to be a lawyer. Then Wolff offers a theory about Kimberly Guilfoyle’s abrupt exit as ambassador, her split from Don Jr. and what she might do next. The conversation turns to Elon Musk, Ukraine’s access to Starlink and Trump’s pursuit of a deal with Putin, before Wolff makes his case for what Trump wants from the world’s richest and most powerful men.

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Michael Wolff and Joanna Coles dig into Kimberly Guilfoyle’s abrupt exit as ambassador to Greece and the leaked messages that preceded it. Why was she pushed out, and what does she know about the Trump family? Wolff argues that her fall exposes a familiar pattern in Trump’s circle: people using power to chase money, status and the next job. They also discuss new White House press secretary Katie Zacharia and why Wolff thinks Trump picked her to be the face of his administration. As the midterms approach, they consider what happens if Trump loses control of Congress but refuses to see it as a defeat. They weigh Elon Musk’s enormous spending on Republican races and what he might expect in return. Then Wolff offers his theory of Trump’s renewed interest in Vladimir Putin, from the deal over Russian diesel to the wealth and influence he believes Trump wants after the White House.

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Michael Wolff and Joanna Coles turn their attention to Pete Hegseth, as the Secretary of Defense is facing mounting criticism over the Iran war while quietly positioning himself for a presidential run. They break down his latest State of the Force speech, which Wolff argues was designed to flatter Donald Trump and win over the MAGA base, and Joanna traces Hegseth’s tough-guy rhetoric back to his time in Iraq. As the war drains American munitions and the midterms approach, they consider whether Trump will make Hegseth the fall guy. But Wolff sees a strange possibility: the louder the calls for Hegseth’s removal become, the less likely Trump may be to fire him. And if Hegseth does lose his job, that may only accelerate his campaign for the next one.

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Michael Wolff and Joanna Coles are counting down to the midterms—and the Trump world is already positioning itself for what comes next. Marco Rubio appears to be launching his 2028 presidential campaign with a grandiose pitch to save Western civilization, while Michael predicts Trump and Rubio may need a new “big thing” to distract from the Iran war, impeachment threats, and mounting investigations. Meanwhile, Kimberly Guilfoyle is engulfed in a stunning new corruption scandal involving hundreds of thousands of dollars as Trump’s political operation increasingly looks like a pay-to-play enterprise. Plus, the Senate map is suddenly tilting toward Democrats, a resurgent measles outbreak threatens RFK Jr.’s political ambitions, and Michael explains why Trump’s team—and Trump himself—may be far more vulnerable after the midterms than they appear.

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Michael Wolff and Joanna Coles examine Donald Trump’s increasingly self-destructive presidency, from his dwindling rally crowds and disastrous political bets to his reckless handling of the war in Iran and increasingly bizarre rhetoric. They draw a remarkable parallel between Trump and disgraced British politician and novelist Jeffrey Archer, another larger-than-life narcissist whose appetite for attention, risk and reinvention eventually brought him crashing down. As Trump doubles down on unpopular policies, loses support among Hispanic voters and inserts himself into midterm races, Wolff asks whether we are watching the beginning of Trump’s downfall—or simply another act in his extraordinary political survival story.

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