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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. #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 00:00 - Will Trump Lose Congress in the Midterms? 04:09 - Can Democrats Flip the Senate? 08:24 - Elon Musk’s Money and the Texas Election 11:32 - Jared Kushner, the Gulf States and Trump’s Corruption 14:44 - Trump, Epstein and the Modeling Agency Connection 19:56 - The Dark World Trump and Epstein Shared 23:05 - Why the Epstein Files Could Hurt Trump 25:25 - What Happens to Trump’s Corporate Cheerleaders? 29:25 - California’s Wealth Tax and the Homelessness Crisis 33:05 - Trump’s Billions and His Family’s Oligarch Dreams 36:47 - Jared Kushner’s Middle East Money Machine 41:30 - How Gulf Money Shapes Trump’s Foreign Policy 44:17 - Why the Media Is Afraid of Trump’s Enablers 48:43 - The Rise of the Political Asshole 52:16 - Trump’s Venezuela Power Grab Could Backfire 56:17 - Trump’s Corruption and His Vendettas 59:25 - Trump’s Strange Noises and Signs of Decline #trump #podcast #news 📖 Title: Why Billions Won’t Save Trump from Crushing Defeat 👂 Podcast: Inside Trump's Head  📺 Episode: 183 🎧 Format:  Full Podcast 📅 Date: October 27, 2026 🎙️ Hosts: Joanna Coles, Michael Wolff Click here to become an official member of the Daily Beast's YouTube community: https://youtube.com/@TheDailyBeast/join Have a question or comment for us? Leave Joanna Coles, Michael Wolff or any of our guests a voicemail in our listener mailbox. Call (929) 274-3577 with your name and message and you may be featured on a podcast or on the Daily Beast. You can also send us an email at [email protected]. The Daily Beast is committed to accurate, fair, independent, fast, and accountable journalism. We seek the truth and report it honestly, without fear or favor. We ground robust and provocative opinions in fact. Subscribe on YouTube: youtube.com/@TheDailyBeast?sub_confirmation=1 Follow us on Instagram: https://instagram.com/thedailybeast Share this video on BlueSky: https://bsky.app/profile/thedailybeast.bsky.social Share this video on X: https://twitter.com/thedailybeast Share this video on Facebook: https://facebook.com/thedailybeast

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