Money, Hubris and Jeffrey Epstein: The Fall of Leon Black, w/ William Cohan

As ballots start to hit mailboxes ahead of the November midterms, Democrats are finally feeling some long-awaited electoral optimism. But to build a coalition that can defeat MAGA politics for good, the party will have to win back voters it's lost. In her new book, “How to Eat An Elephant,” Sarah Longwell, founder and publisher of The Bulwark, gives readers a blueprint to do just that. In a live conversation recorded at Sixth & I in downtown Washington, D.C., Kara and Sarah talk about the hundreds of voter focus groups Sarah’s conducted since President Trump first won the White House a decade ago, how Trump convinced swing voters he was the “lesser of two evils” in 2024, and why she thinks Democrats need a stronger message on immigration. Sarah also offers her opinion on which Democrats are — and are not — best positioned to win the White House in 2028. Questions? Comments? Email us at [email protected] or find us on YouTube, Instagram, TikTok, Threads, and Bluesky @onwithkaraswisher. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ripple CEO Chris Larsen once told Kara he’d rather vomit blood out of his eyeballs than run for public office. But that doesn’t mean he won’t use his wealth to influence politics or install a Flock surveillance system that helps the San Francisco Police Department. The latter has some civil liberties advocates crying foul. Kara presses Larsen on everything from surveillance, the AI arms race, cryptocurrency regulations, California's billionaire tax ballot measure, and the midterms. This conversation was recorded live at San Francisco’s Pier 27 as part of the Odoo Experience. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ahead of the midterms and what’s shaping up to be an intense political season, Kara speaks with the Democratic mayors of three cities dealing with some of the biggest issues facing the nation including affordability, housing, gerrymandering and immigration.  Mike Johnston is the first-term Mayor of Denver, Colorado. A former teacher, school principal and Colorado state senator, Mike is also a vice president of the Democratic Mayors Association. Quinton Lucas is the Mayor of Kansas City, Missouri, currently in his second term. He’s also the youngest person elected to the role since 1855. An attorney and former city councilman, Quinton is the President of the Democratic Mayors Association.  Helena Moreno is the Mayor of New Orleans. She began her first term in office this year. Previously she served on the city council and as a Louisiana state legislator. Before getting into politics, she worked as a journalist. She’s the first Latina mayor of New Orleans and the city’s second woman mayor. Questions? Comments? Email us at [email protected] or find us on YouTube, Instagram, TikTok, Threads, and Bluesky @onwithkaraswisher. Learn more about your ad choices. Visit podcastchoices.com/adchoices

In his new book, “Money To Burn,” author and Puck journalist William Cohan traces the rise and fall of one of Wall Street’s most towering modern figures: billionaire Leon Black. His private equity and investment firm, Apollo, changed Wall Street, making Black enormously rich. He reached the highest rungs of New York society, but his ties to convicted sex criminal Jeffrey Epstein ultimately took him down. Kara and Bill talk about how Black and Apollo ushered in a "new Wall Street" and the nature of Black's relationship with Epstein, which continued for almost a decade after Epstein's 2008 conviction for soliciting prostitution from a minor. They also break down some of the latest headlines in business and finance, including Meta’s $17 billion settlement and President Trump’s escalating trade war with Canada. Questions? Comments? Email us at [email protected] or find us on YouTube, Instagram, TikTok, Threads, and Bluesky @onwithkaraswisher.  Learn more about your ad choices. Visit podcastchoices.com/adchoices

Across the country, people continue to grieve Dolly Parton, the late country music icon who spent more than 60 years making us cry, laugh and fall in love. But in a country as fragmented and divided as the U.S., how did Dolly Parton become our "unproblematic fave”? In this bonus episode of On With Kara Swisher, Kara breaks down the legendary artist many call Saint Dolly with three Dolly experts. Tressie McMillan Cottom⁠ is a professor of sociology at the University of North Carolina - Chapel Hill, a culture critic and an award-winning author. Her latest New York Times column is titled, “Loving Dolly Was Easy. Understanding Her Was Hard.” Chely Wright is a country music artist and author of the book “Like Me: Confessions of a Heartland Country Singer." And Marissa Moss is a writer for Rolling Stone and author of the book “Her Country: How the Women of Country Music Became the Success They Were Never Supposed to Be.” Questions? Comments? Email us at [email protected] or find us on YouTube, Instagram, TikTok, Threads, and Bluesky @onwithkaraswisher. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Today we’re bringing you an episode of a new podcast called “Why Are You Like This? with Megan Rapinoe” from A Touch More and the Vox Media Podcast Network.  Live from WNBA All Star Weekend, host Megan Rapinoe sits down with five-time All-Star coach Cheryl Reeve, the winningest coach in WNBA history.  Cheryl Reeve has been head coach of the Minnesota Lynx since 2010. In addition to leading the team to four WNBA world championships, Reeve supported the Lynx’s 2016 protest against police brutality and continues to advocate for social justice issues in Minneapolis and beyond, including as an outspoken supporter of transgender athletes.  Megan and Cheryl get into how she’s evolved as a coach, the WNBA’s legacy of activism and why she’s proud of a league where “everyone is so authentically themselves.”  Why Are You Like This? is a co-production of A Touch More and Vox Media Podcast Network. New episodes every Thursday. Follow Megan on Instagram: https://www.instagram.com/mrapinoe/  Follow A Touch More on Instagram: https://www.instagram.com/whyareyoulikethis/  Follow A Touch More on TikTok: https://www.tiktok.com/@whyareyoulikethis Learn more about A Touch More here: https://www.atouchmore.com Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ina Garten has built a culinary empire by way of simple, delicious recipes for the home cook. After two decades on The Food Network and more than a dozen cookbooks, she’s launching a new podcast with the Vox Media Podcast Network next month, called “Happy Hour With Ina Garten.” It’s her latest professional pivot in a career that’s been full of them. Ina and Kara talk about Ina’s plans for her new show, making the leap from traditional platforms to independent media, and what she'll get to do on podcasts that she couldn't do on TV. They also talk about the ways social media is reshaping our relationship to cooking and the people Ina turns to for inspiration. Happy Hour with Ina Garten premieres Wednesday, September 16th. Subscribe to the show on YouTube, Apple Podcasts, Spotify, or wherever you get your podcasts. Questions? Comments? Email us at [email protected] or find us on YouTube, Instagram, TikTok, Threads, and Bluesky @onwithkaraswisher. Learn more about your ad choices. Visit podcastchoices.com/adchoices

There's a lot going on across the tech, media and legal landscape, from the potential $111 billion Paramount-Warner Bros. merger, to landmark social media addiction rulings and a series of even bigger upcoming trials.  Eriq Gardner is a founding partner and national correspondent at Puck who mostly writes about legal affairs. He joins Kara to unpack some of the biggest stories on his beat, including the latest on California Attorney General Rob Bonta's 12-state antitrust lawsuit against Paramount, the politics behind the deal and whether a settlement is imminent.  Kara and Eriq also discuss what, if anything, could put the brakes on President Trump's many defamation cases against media companies. Plus, they look at why publishers pursue litigation against some AI companies even while they're making content-licensing agreements with others.  Questions? Comments? Email us at [email protected] or find us on YouTube, Instagram, TikTok, Threads, and Bluesky @onwithkaraswisher. Come see Kara for a live taping of On at the Odoo Experience conference in San Francisco on September 2. Register for the conference on Odoo's website. Learn more about your ad choices. Visit podcastchoices.com/adchoices

While the Greek and Roman philosophy of Stoicism has been around for millennia, author and media strategist Ryan Holiday is bringing its teachings to a modern audience by way of his popular books and his podcast, “The Daily Stoic.” He says ancient writings by the likes of Seneca, Marcus Aurelius, and Epictetus resonate in times that feel especially chaotic. Kara and Ryan talk about why young men in particular seem drawn to Stoicism and what powerful figures in the worlds of tech, MAGA politics, and the man-o-sphere get wrong about its teachings. He tells Kara their actions frequently run counter to Stoicism’s foundational tenet: our obligation and responsibility to — and with — other people. Questions? Comments? Email us at [email protected] or find us on YouTube, Instagram, TikTok, Threads, and Bluesky @onwithkaraswisher.  Learn more about your ad choices. Visit podcastchoices.com/adchoices

Elon Musk’s SpaceX debuted on the Nasdaq in June with the largest IPO ever, raising a record $86 billion. But the stock has been on a wild ride ever since. Kara sits down with a panel of experts to assess SpaceX after its inaugural post-IPO earnings report and the first in a series of lockup expirations that released more than 900 million shares for trading. They break down where SpaceX is actually making money (spoiler: it’s Starlink) and what its massive AI spending, xAI acquisition and increasingly expansive ambitions reveal about Musk’s long-term strategy.  Ed Elson is an analyst, writer, and co-host of the Prof G Markets podcast from the Vox Media Podcast Network. Tim Higgins is a business columnist for The Wall Street Journal, a CNBC contributor, and the author of books including iWar: Fortnite, Elon Musk, Spotify, WeChat, and Laying Siege to Apple’s Empire. Bethany McLean is a contributing editor at Vanity Fair, a columnist at Yahoo Finance, a CNBC contributor, and the author of books including The Smartest Guys in the Room: The Amazing Rise and Scandalous Fall of Enron. Questions? Comments? Email us at [email protected] or find us on YouTube, Instagram, TikTok, Threads, and Bluesky @onwithkaraswisher. Come see Kara for a live taping of On at the Odoo Experience conference in San Francisco on September 2. Register for the conference on Odoo's website. Learn more about your ad choices. Visit podcastchoices.com/adchoices