Episodes

Michael Wolff and Joanna Coles head into the midterms with a look at the fights gathering around Donald Trump. Wolff shares an update on his legal battle with Melania Trump, then the hosts turn to former Trump lawyer Alina Habba’s reported $50 million deal and her clash with Trump over money and influence. Wolff argues that the dispute could be an early sign of a wider scramble among people close to the president. They also size up vulnerable MAGA candidates, ask whether falling Fox News ratings signal trouble for Trump and consider what Tuesday’s results could mean for his grip on the Republican Party. #ad For a limited time, get 60% off your first order, plus free shipping and free treats for life, when you head to https://Smalls.com/HEAD #ad INCOGNI Deal: To get an exclusive 60% off an annual Incogni plan, go to https://incogni.com/beast Learn more about your ad choices. Visit podcastchoices.com/adchoices

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. #ad For a limited time, get 60% off your first order, plus free shipping and free treats for life, when you head to https://Smalls.com/HEAD #ad INCOGNI Deal: To get an exclusive 60% off an annual Incogni plan, go to https://incogni.com/beast Learn more about your ad choices. Visit podcastchoices.com/adchoices

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. #ad Go to https://san.com/insidetrumpshead to get the unbiased truth on the stories that matter, only on the Straight Arrow app. Let’s exit the echo chamber. 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 Learn more about your ad choices. Visit podcastchoices.com/adchoices

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 Learn more about your ad choices. Visit podcastchoices.com/adchoices

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

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

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

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

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

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

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

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

Michael Wolff and Joanna Coles reveal the fears they believe drive Donald Trump—from being exposed as unintelligent and unable to absorb information to his dread of rejection, ridicule, loneliness, and losing the spotlight. Wolff recounts the extraordinary efforts allegedly made to keep Trump’s academic records hidden, explains why ordinary conversation can leave him vulnerable, and describes a president who needs an audience but recoils from genuine human contact. As they trace how these insecurities shape his attacks, obsessions, and refusal to accept defeat, Wolff offers a chilling prediction of how Trump could preserve his power after leaving office—and why his hunger for attention may never let him disappear. #ad Download Saily's app and use code beast at checkout to get an exclusive 15% off your first purchase! For further details go to https://saily.com/beast #ad For a limited time, get 60% off your first order, plus free shipping and free treats for life, when you head to https://Smalls.com/HEAD. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Michael Wolff and Joanna Coles take a revealing look inside Donald Trump’s world of flunkies, fear and humiliation, where cabinet officials, billionaires and tech titans learn how far they have to bend to stay in his good graces. They examine why figures like Marco Rubio, J.D. Vance and Pete Hegseth have accepted radically different versions of the same bargain, and how Trump’s unpredictable mix of praise and fury keeps those around him off balance. They also explore his treatment of women, including the leaked images of Trump berating Natalie Harp, before Wolff explains why, in Trump’s second term, almost nobody around him can afford to believe they are his equal. #ad For a limited time, get 60% off your first order, plus free shipping and free treats for life, when you head to https://Smalls.com/HEAD. #ad Download SAILY's app and use code beast at checkout to get an exclusive 15% off your first purchase! For further details go to https://saily.com/beast Learn more about your ad choices. Visit podcastchoices.com/adchoices

Michael Wolff and Joanna Coles dig into what Donald Trump’s political future looks like as the midterms approach, from Republicans increasingly distancing themselves from Trump to his apparent determination to double down rather than retreat. They examine Trump’s taxpayer-funded campaign ad, the Texas Senate race, and the growing fight over AI data centers before turning to the darker story of Jeffrey Epstein—and Wolff’s firsthand account of Epstein’s fear of Trump becoming president, the collapse of their friendship, and the extraordinary events surrounding Epstein’s arrest and death. As Wolff revisits what Epstein told him about Trump and why he believed his old friend was capable of anything, the conversation opens up a much darker side of Trump’s history that is impossible to ignore. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Michael Wolff and Joanna Coles take a closer look at Donald Trump’s encounter with Xi Jinping and what China may have learned from a president they see as unusually susceptible to flattery, especially when it comes to the delicate question of Taiwan. They also dissect Melania Trump’s new women’s network, the growing role of billionaires around the White House, and the extraordinary rise of Kimberly Guilfoyle from Fox News to ambassador to Greece, including the business and personal relationships now surrounding her diplomatic role. Then, the conversation turns to Trump’s escalating fight with the press and the uncertain future of CNN as its ownership changes hands, before Wolff and Coles weigh in on the memoirs of Bob Chapek and Ari Emanuel and what they reveal about a rapidly changing media and entertainment industry. #ad INCOGNI Deal: To get an exclusive 60% off an annual Incogni plan, go to https://incogni.com/beast 🛡️ Learn more about your ad choices. Visit podcastchoices.com/adchoices

Michael Wolff and Joanna Coles unpack Trump’s latest threats to “annihilate” Iran, including the bizarre White House effort to find him a new word after “obliterate” apparently lost its punch. They discuss Trump’s UN week showdown with world leaders, Xi Jinping’s visit to the White House, Melania Trump’s new women’s initiative, and RFK Jr.’s extraordinary $4 million book deal. They also examine the devastating testimony from families affected by ICE shootings in Minneapolis and what it could mean as the midterms approach, before turning to the widening Republican Senate map and the chaos surrounding Trump’s proposed White House ballroom. With Trump declaring “I am the code” as questions swirl around the building’s safety regulations, Michael and Joanna trace the larger pattern behind a president who refuses to accept limits, rules or anyone telling him what he can and cannot do. #ad INCOGNI Deal: To get an exclusive 60% off an annual Incogni plan, go to https://incogni.com/beast 🛡️ Learn more about your ad choices. Visit podcastchoices.com/adchoices

Michael Wolff and Joanna Coles return to dissect Donald Trump’s latest battle with the press, his launch of Trump TV, and the high-stakes arrival of Chinese President Xi Jinping at the White House. They examine why Trump keeps turning the media into his enemy, what his escalating wars and increasingly precarious relationship with China could mean for the United States, and how a meeting with Xi could reshape the balance of power around Taiwan and beyond. They also look at Trump’s claims about military installations, his reliance on spectacle and conflict to dominate the news cycle, and the looming midterms, where Democrats may be tempted to read too much into Trump’s current political troubles. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Michael Wolff and Joanna Coles dig into what may be the most revealing signs yet of a White House struggling to manage Donald Trump, as his own advisers begin publicly pushing back on his dismissal of AI concerns and his refusal to confront Republican vulnerability ahead of the midterms. They examine Trump’s increasingly personal battle with the Kennedy Center, including his reported plans to demolish it, before turning to his fixation on 1950s battleships, the Supreme Court, and the idea that everyone in government ultimately works for him. They also discuss the Epstein files, soaring gas prices, the fallout from the Iran war, Trump’s claims about Greenland, and the looming constitutional questions surrounding the next Congress. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Michael Wolff and Joanna Coles examine Donald Trump's growing political troubles as rising prices, escalating tensions in the Middle East, and his own economic policies threaten to make affordability his biggest liability ahead of the midterms. They discuss Trump's pressure on the Federal Reserve, the consequences of his tariffs and war policies, and why his administration's approach may be fueling the very problems he claims he wants to solve. Plus, Melania Trump's surprising enthusiasm for AI, the latest turmoil at the Kennedy Center, and the court's refusal to let Trump put his name on the building. They also take a closer look at Kash Patel's purge of senior FBI agents, the changing standards for joining the bureau, and Lee Greenwood's wife's nomination as ambassador to Barbados. As Trump surrounds himself with loyalists and pushes aside voices that might challenge him, Michael and Joanna consider whether his own decision-making is setting the stage for a political reckoning. #ad Ready to reach your goals? Visit https://hims.com/ith to get a personalized, affordable plan that gets you. #ad Try QUO for free plus get 20% off your first 6 months at https://www.quo.com/BEAST. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Michael Wolff and Joanna Coles look at Donald Trump’s escalating battles with the Supreme Court, the collapse of the Kennedy Center under his control, and his increasingly aggressive response to the AI debate, where Trump has declared that “whoever wins AI wins” while threatening critics and accusing them of conspiracy. They also examine Trump’s rollback of climate protections, his approach to conflict as a political strategy, and the extraordinary allegations surrounding Donald Trump Jr.’s wedding and its Russian connections. Plus, Trump’s threat against Oman, the consequences of burning through missile supplies in Iran, Jared Kushner’s transformation of American diplomacy into a business operation, and what a post-Trump administration could look like if Democrats make major gains in the midterms. #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

Michael Wolff and Joanna Coles unpack Donald Trump’s trip to Ireland, his apparent struggle to stay awake at a 9/11 memorial, and the increasingly conspicuous signs that the president’s hold on his party may be starting to weaken. They dig into JD Vance’s careful balancing act between loyalty to Trump and positioning himself as his successor, including the growing machinery behind a potential 2028 campaign, before turning to RFK Jr.’s surprisingly commanding performance at the Republican mini-convention and the extraordinary political path that brought him into Trump’s orbit. Ted Cruz also makes his inevitable return, while Trump’s own reaction to the prospect of a Republican successor looms over the entire discussion. Finally, Michael and Joanna take a close look at the new E. Jean Carroll documentary, her decision to come forward, the consequences she faced, and why her story takes on an even more powerful dimension when told in her own words. Learn more about your ad choices. Visit podcastchoices.com/adchoices

INCOGNI Deal: To get an exclusive 60% off an annual Incogni plan, go to https://incogni.com/beast 🛡️ #ad Michael Wolff and Joanna Coles dissect Donald Trump’s latest spectacle, from his bizarre claim that he was a hero at Ground Zero following 9/11 to the half-empty Republican convention in Dallas that Trump insists was packed. They look at why Trump is dragging himself into the midterm elections despite his deeply unpopular standing, and Wolff argues that the bigger strategy is to make sure the Republican Party never imagines life without him. They also examine Trump’s escalating war with Iran, his efforts to sow confusion around mail-in voting, and his habit of announcing major policies and promises in the moment, including $5,000 checks for every American adult if Republicans win. Then comes the strangest mystery of all: why Trump handed out tens of thousands of dollars in cash to members of his inner circle, including a $45,000 payment to Natalie Harp, and Wolff offers his theory about what those payments may have bought. The episode also gets into Jimmy Kimmel’s fight with the Trump administration, the growing power of YouTube over traditional television, and why the media business itself may be undergoing a transformation that Trump is accelerating. #ad For a limited time, get 60% off your first order, plus free shipping and free treats for life, when you head to https://Smalls.com/HEAD. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Michael Wolff and Joanna Coles dissect Donald Trump’s latest transformation, from his dramatically darker hair and increasingly bizarre AI images to the social-media strategy that has turned political spectacle into a powerful weapon. They look at Trump’s influence on the surging far right across Europe, why Wolff believes Trump may be the cause rather than merely the symptom of the global populist wave, and whether a Russia-Ukraine peace deal could give Trump the ultimate midterm “October surprise.” They also examine the growing pressure on Pete Hegseth, the extraordinary purge of military leaders, and the leak-hunting campaign inside the Pentagon before turning to Mitch McConnell's continued absence, John Fetterman, and a new breed of politician who treats convention, competence, and even showing up for the job as optional. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Michael Wolff and Joanna Coles take on Donald Trump’s increasingly bizarre relationship with Vladimir Putin as Jared Kushner and Steve Witkoff head to Moscow, asking what Trump’s Russia fixation is really about and why Putin seems so comfortable dealing directly with Trump’s inner circle. They also dissect Trump’s obsession with the Qatari plane, his plans to leave a permanent physical mark on the White House, and the latest battle over his triumphal arch. Then, Maria Bartiromo’s sudden departure from Fox News opens a revealing discussion about her long relationship with Trump and the network’s transformation under the Murdoch family, before Melania Trump’s conspicuous absence from the GOP’s midterm gathering raises fresh questions about the state of the Trump marriage. Finally, Wolff and Coles turn to the chaos at the Pentagon, where dozens of officials are being subjected to lie-detector tests as Pete Hegseth faces mounting questions about his leadership and the military’s ability to function. #ad Free trial at https://shopify.com/dailybeast Learn more about your ad choices. Visit podcastchoices.com/adchoices

Michael Wolff and Joanna Coles look at Donald Trump’s long-standing appetite for power, from his determination to get around courts and regulations to the possibility that he could use his enormous political war chest to maintain influence long after leaving office. They examine the growing crisis around Pete Hegseth, why Trump appears threatened by competence, and how the war with Iran is exposing deeper failures in American leadership. They also trace the economic risks tied to tariffs, interest rates and the massive AI boom, before turning to the increasingly volatile 2026 midterms, dark money, mail-in voting and the presence of U.S. Marshals at polling places. #ad Download SAILY's app and use code beast at checkout to get an exclusive 15% off your first purchase! For further details go to https://saily.com/beast Learn more about your ad choices. Visit podcastchoices.com/adchoices

Description Michael Wolff and Joanna Coles look at the extraordinary power dynamics surrounding Donald Trump, beginning with Melania Trump’s increasingly independent role—and how she has managed to monetize the position of First Lady while largely avoiding its traditional obligations. They also examine Trump’s White House ballroom and a Supreme Court decision that may allow construction to continue, the president’s attacks on NBC’s Kristen Welker and the growing fear his administration inspires across the media, and Pete Hegseth’s purge of experienced military leaders at a moment of heightened global danger. Then the conversation turns to an unlikely political flashpoint: data centers, as growing public opposition to their enormous demands for power and water collides with Trump’s fierce support for the AI industry—and his own financial interests. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Michael Wolff and Joanna Coles look ahead to the midterms and ask whether Donald Trump’s political dominance is finally starting to crack—or whether Democrats are getting ahead of themselves. They break down the unreliable polling, Trump’s unusual ability to bring hesitant voters back to his side at the last moment, the races that could determine control of the House and Senate, and the surprising Republican confidence that they can hold key states including Texas. They also examine Trump’s record of backing risky candidates like Ken Paxton, the enormous sums being poured into competitive races, and how Trump is already trying to shape the rules of the election through mail voting restrictions, redistricting and polling-place monitoring. But the most consequential question comes at the end: if Trump loses and declares the election rigged, will the people around him finally distance themselves—or once again follow him beyond the bounds of what is politically acceptable? #ad Head to https://Superpower.com and use code BEAST at checkout for $20 off your membership. Unlock your new health intelligence. 100+ biomarkers. Every year. Detect early signs of 1,000+ conditions. #superpowerpod Learn more about your ad choices. Visit podcastchoices.com/adchoices

Michael Wolff and Joanna Coles look at the latest signs of chaos inside Trump’s White House, from the administration’s fixation on interest rates and the tensions surrounding the Federal Reserve to the startling questions raised by the CIA chief’s trip to Moscow and the Pentagon’s increasingly strange leadership. They also turn to the extraordinary bubble surrounding Trump, including Natalie Harp’s role in feeding him the information he wants to see, before considering what it all could mean as the 2026 midterms rapidly approach. #ad Ready to reach your goals? Visit https://hims.com/ith to get a personalized, affordable plan that gets you. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Michael Wolff and Joanna Coles take on Donald Trump’s latest fixation with image, power, and excess, from his apparent weight gain and the extraordinary Mar-a-Lago golf club buffet to the increasingly curious role of Natalie Harp and her place in Trump’s orbit. They explore why Trump’s celebrity, sexual bravado, and ability to attract devoted followers remain central to his political appeal, before turning to the explosive meeting between Jared Kushner and Hakeem Jeffries that has White House staffers furious and raises an awkward possibility for Trump’s party heading into the midterms. They also look at Trump’s ballroom project, the hidden military machinery beneath the White House, the fate of America’s wild mustangs, and the larger cultural reckoning over football and brain injuries. Learn more about your ad choices. Visit podcastchoices.com/adchoices