Episodes

  • This Is the Sordid Reason Trump Bows to Putin

    This Is the Sordid Reason Trump Bows to Putin
    Oct 23 2026
    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. #ad Ready to reach your goals? Visit https://hims.com/ith Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    1 hr and 33 mins
  • I Know What Trump Will Do After Crushing Defeat

    I Know What Trump Will Do After Crushing Defeat
    Oct 21 2026
    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. Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    48 mins
  • I Know Who Will Go Next in Trump's Reign of Chaos

    I Know Who Will Go Next in Trump's Reign of Chaos
    Oct 18 2026
    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. Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    1 hr and 7 mins
  • This Is Trump's Sinister Plot Against His Own Aide

    This Is Trump's Sinister Plot Against His Own Aide
    Oct 16 2026
    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. #ad https://quo.com/beast Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    58 mins
  • I Know Real Reason Trump Fired Kimberly Guilfoyle

    I Know Real Reason Trump Fired Kimberly Guilfoyle
    Oct 14 2026
    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. #ad https://quo.com/beast Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    58 mins
  • This Is Laughable Truth About Trump's 'Tough Guy'

    This Is Laughable Truth About Trump's 'Tough Guy'
    Oct 11 2026
    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. #ad Unlock your best hair & skin with @iRestorelaser and HUGE savings on iRESTORE with code BEAST at https://irestore.com/BEAST ! #irestorepod Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    45 mins
  • Kimberly Guilfoyle's Money Secrets Just Exploded

    Kimberly Guilfoyle's Money Secrets Just Exploded
    Oct 9 2026
    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. #ad Unlock your best hair & skin with @iRestorelaser and HUGE savings on iRESTORE with code BEAST at https://irestore.com/BEAST ! #irestorepod Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    1 hr and 6 mins
  • Why Trump's Self-Destruction Is Finally Happening

    Why Trump's Self-Destruction Is Finally Happening
    Oct 7 2026
    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. Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    57 mins