Greg Olear talks to Candace Rondeaux about her book “Putin’s Sledgehammer,” which delves into the Wagner Group mercenary group and the complexities of Russia’s political landscape. Rondeaux shares her background in journalism and her journey into understanding Russian geopolitics, particularly through the lens of the Wagner Group and its leader, Yevgeny Prigozhin. The discussion covers the origins of the Wagner Group, Prigozhin’s rise and fall, the influence of figures like Alexander Dugin, and ...
Jun 17, 2025•1 hr 9 min
Greg Olear talks to John B. King, Jr., former U.S. Secretary of Education and current SUNY chancellor, about what the Department of Education actually does; what proposed cuts to the D.O.E. mean for students, teachers, parents, and communities; the impact of the COVID-19 pandemic on student learning; the stakes of the Trump Administration’s ongoing attacks on higher education; and his powerful and moving new memoir, “Teacher by Teacher: The People Who Save Our Lives.” John B. King Jr. served in ...
May 27, 2025•53 min
Greg Olear talks to Nicolo Majnoni about his new podcast, 'Shadow Kingdom, God's Banker,' which delves into the mysterious death of banker Roberto Calvi and the intricate financial systems of the Vatican. Majnoni shares his personal connection to the Vatican, the complexities of its banking operations, the historical context of its wealth, and the shadowy organization P2, as well as the future challenges facing the papacy amidst financial chaos. They discuss the connections between organized cri...
May 06, 2025•56 min
Who owns the land? Who DECIDES who owns the land? Who has the power to redistribute land ownership? If land ownership IS redistributed, who gets to take possession and who doesn’t? And what adverse impact can the reshuffling of land ownership have on our society and our planet? Greg Olear talks to Michael Albertus, a professor at the University of Chicago and the author of Land Power: Who Has It, Who Doesn't, and How That Determines the Fate of Societies , about these and other questions pertain...
Apr 18, 2025•53 min
To, ahem, sever himself from the news, Greg Olear brings on his wife, Stephanie St. John, a huge fan of “Severance,” to discuss the second season. Cold Harbor, fetid moppet, devour feculence, Helly/Helena, the Glasgow Block, ORTBO, the four tempers, and more goats than anyone asked for: they cover it all, with verve and wiles. Make America Great Gatsby Again! https://bookshop.org/p/books/the-great-gatsby-four-sticks-press-centennial-edition/e701221776c88f86?ean=9798985931976&next=t Subscribe...
Apr 11, 2025•1 hr 6 min
The Overwhelm: Trump, Musk, stupidity, banality, artlessness, lack of decency, betrayal by our leadership, rage, fear, grief from what we’ve lost. We are living through a period of national, if not global, trauma. Actor and trauma coach Claudia Black returns to PREVAIL to talk about the causes of trauma, how to heal from it, emotional aid, and what we can do to regulate ourselves. Claudia’s website is here: https://claudiablackconsulting.com/what-i-do Make America Great Gatsby Again! https://boo...
Mar 14, 2025•1 hr 48 min
Katherine Stewart is the author of The Power Worshippers: Inside the Dangerous Rise of Religious Nationalism, the award-winning book upon which the documentary feature, God & Country, produced by Rob Reiner and Michele Reiner, is based. She has covered the intersection of faith and politics for over 15 years; her work appears in the New York Times, The Washington Post, the New Republic, the Guardian, and Religion News Service, and she has been featured on broadcast media outlets such as MSNB...
Feb 21, 2025•1 hr 7 min
Christopher Steele began his twenty-two-year career as an intelligence professional and Russia expert within the British government in 1987, soon after graduating from Cambridge University. He was posted to Moscow, where he served through the fall of the Soviet Union, and Paris, before returning to London to become one of the government’s senior intelligence experts and advisers on Russia. In 2009, he founded the private intelligence company Orbis Business Intelligence. His series of intelligenc...
Jan 17, 2025•1 hr 15 min
For more than 30 years, Alexandra Hall Hall worked as a diplomat in the British Foreign Office, with postings in Washington, Bangkok, Delhi, Bogota, and Tbilisi, where she was the British ambassador to Georgia. She is now the co-host of the Disorder podcast. This is an interview from Friday’s episode of THE FIVE 8. Having just returned from Tbilisi, she talks about the situation there. Plus: Holly Jolly. Follow Alex Hall-Hall: https://bsky.app/profile/alexhh.bsky.social Make America Great Gatsby...
Dec 20, 2024•47 min
Many times in the last two years, we have warned about the grim consequences of allowing a wannabe dictator–who attempted to overthrow the government on his way out the door four years ago–back into the White House. What we warned about has happened. We are 45 days away from Donald Trump’s second inauguration. And based on who the Mussolini of Queens has picked for his cabinet and staff positions, it looks like he was dead serious about being a dictator on Day One. This week, I will replay clips...
Dec 06, 2024•1 hr 29 min
Make America Great Gatsby Again! https://bookshop.org/p/books/the-great-gatsby-four-sticks-press-centennial-edition/e701221776c88f86?ean=9798985931976&next=t Subscribe to The Five 8: https://www.youtube.com/channel/UC0BRnRwe7yDZXIaF-QZfvhA Check out ROUGH BEAST, Greg’s new book: https://www.amazon.com/dp/B0D47CMX17 ROUGH BEAST is now available as an audiobook: https://www.audible.com/pd/Rough-Beast-Audiobook/B0D8K41S3T Would you like to tell us more about you? http://survey.podtrac.com/start...
Nov 22, 2024•1 hr 21 min
Jimmy Kennedy was the executive producer of the first season of The Noel Casler Podcast, the afternoon drive producer for The Kent Sterling Show on CBS Sports 1430 AM in Indianapolis, and a gameday staff member with the Indianapolis Colts of the National Football League. He is currently the host and producer of his own show, JBK On Air, where he interviews a variety of guests including athletes, political commentators, media personalities, & more. Jimmy, who has cerebral palsy, is a longtime...
Nov 15, 2024•1 hr 14 min
This episode of the live YouTube show “The Five 8” was recorded on Wednesday, November 6, 2024–the night after the election. It is not the show we planned to do, certainly not the show we wanted to do, but the show we had to do. Featuring Stephanie “LB” Koff and Greg Olear. Make America Great Gatsby Again! https://bookshop.org/p/books/the-great-gatsby-four-sticks-press-centennial-edition/e701221776c88f86?ean=9798985931976&next=t Subscribe to The Five 8: https://www.youtube.com/channel/UC0BRn...
Nov 08, 2024•1 hr 19 min
It’s been just over 100 days since Kamala Harris officially replaced Joe Biden at the top of the ticket, but it feels like an eternity. With just four days until the most consequential presidential election since 1860, Greg Olear talks to OSINT researcher ne plus ultra Gal Suburban about what to expect on Election Day–and, more ominously, what schemes may come in the weeks after the election is decided. Among the topics discussed: Elon Musk, Mike Flynn, JD Vance, Maria Butina, and more. Plus: a ...
Nov 01, 2024•1 hr 33 min
Tom Kemp is a Silicon Valley-based entrepreneur, seed investor, policy advisor and author of the award-winning bestseller Containing Big Tech: How to Protect our Civil Rights, Economy, and Democracy . Tom was the founder and CEO of Centrify, a leading cybersecurity cloud provider. As an angel investor, he’s made seed investments in over fifteen tech start-ups. He has also served as a volunteer technology policy advisor for political campaigns, legislators, and civil society groups. His advocacy ...
Oct 18, 2024•1 hr 15 min
Nina Burleigh is a journalist, best-selling author, documentary producer, and publisher of a Substack on politics called American Freakshow . A contributing editor at The New Republic and frequent contributor to the New York Times and New York Magazine, she is the author of eight books on an array of topics including archaeological forgery, scientists in 18th Century Egypt, James Smithson, Amanda Knox in Italy, the Trump women, and the pandemic response. Her latest book, and first novel, is call...
Oct 11, 2024•1 hr 33 min
Gareth Gore is a financial journalist and editor with close to two decades of experience, who has reported from over twenty-five countries and covered some of the biggest financial stories. His writing has been published by Bloomberg, Thomson Reuters, and International Financing Review. He is the host of The Syndicate, which tells the behind-the-scenes stories of the biggest financial deals in history. His new book, five years in the making, is “OPUS: The Cult of Dark Money, Human Trafficking, a...
Oct 04, 2024•1 hr 20 min
David Daley is the author of the national best-seller “Ratf**ked: Why Your Vote Doesn’t Count” and “Unrigged: How Americans Are Battling Back to Save Democracy.” His journalism on democracy and voting rights appears regularly in The New Yorker, The New York Times, The Atlantic, The Washington Post, Slate, The New Republic and many other publications. He is the former editor in chief of Salon, and has taught journalism and political science as a fellow at Wesleyan University, Boston College and t...
Sep 27, 2024•1 hr 22 min
Anthony Comstock (1844-1915) would be nothing more than a footnote from an ugly, retrograde, and bygone period of American history, except that Dobbs made the laws that bear his name suddenly relevant again. But who was Comstock? What made him such a woman-hating weirdo? Why did he hold sway for so long, and how was Comstockery defeated? Amy Sohn, the author of “ The Man Who Hated Women: Sex, Censorship & Civil Liberties in the Gilded Age ,” talks to Greg Olear about all things Comstock: who...
Sep 20, 2024•1 hr 13 min
Greg Olear talks to Stephanie Baker about her superb new book, “Punishing Putin: Inside the Global Economic War to Bring Down Russia,” on the West’s financial warfare against Putin after the invasion of Ukraine. They discuss the oligarchs and their complex relationships with Putin, the challenges of implementing economic sanctions on an economy as big as Russia’s, Boris Johnson’s role in the push for sanctions, the unintended consequences and byproducts of the economic warfare, the role of Teleg...
Sep 13, 2024•1 hr 22 min
In this far-ranging discussion, Greg Olear talks to the actress, director, podcast host, and activist Rosanna Arquette about: Kamala Harris, the DNC, and the new hope around U.S. politics; what to expect at the presidential debate; the deal with RFK Jr.; the time she met Trump; the time she met Dr. Martin Luther King, Jr.; the Alexis Project and the fundraiser happening in LA this week; Me Too and opportunities for women in Hollywood; her acting career, from “Desperately Seeking Susan” to “Pulp ...
Sep 06, 2024•1 hr 30 min
Robbie Harris is a strategic communications and behavior change subject matter expert with over 25 years’ experience working with local influencers, activists, civil society organizations, journalists, and senior stakeholders in Iraq, Syria, Africa, and Central America. She has designed and implemented successful programs for US DoD, DoS and USAID, and UK FCDO and MoD. She’s the co-founder of a small international business; has worked for USAID-OTI; speaks Arabic, Spanish, and English, and has a...
Aug 23, 2024•1 hr 13 min
Greg talks with the historian Manisha Sinha and discusses her book “The Rise and Fall of the Second American Republic: Reconstruction, 1860-1920.” The book explores the period between the Civil War and World War I, highlighting the importance of Reconstruction in shaping the country. Sinha explains her motivation for writing the book and the significance of the Second American Republic. She also draws parallels between Andrew Johnson and Donald Trump, emphasizing the consequences of showing merc...
Aug 16, 2024•1 hr 29 min
For 26 years, Rone Tempest was the national and foreign correspondent for the LA Times, based in Paris, New Delhi, Beijing, and Hong Kong, as well as the craziest capital city, Sacramento. After his retirement, he worked for Pro Publica and was the co-founder of the Wyoming nonprofit public policy news site, Wyofile. He’s taught journalism at Berkeley, his alma mater, and has won numerous awards. He’s also the author of two books, including “The Last Western: The Unjustified Killing of Michael R...
Aug 09, 2024•1 hr 28 min
Francine Prose is the author of over 30 books. Her 12 novels include My New American Life, A Changed Man and Blue Angel , a finalist for the National Book Award. Her nonfiction works include the indispensable Reading Like a Writer ; Caravaggio: Painter of Miracles ; and The Lives of the Muses: Nine Women and the Artists They Inspired, a New York Times Notable Book for 2002. She’s a contributing editor at Harper's , and her essays, reviews, and criticism have appeared in New York Times Book Revie...
Aug 02, 2024•1 hr 18 min
In this, the penultimate episode of Season 7 of the PREVAIL podcast, Greg Olear discusses (for a solid 20 minutes, which is probably too long, if we’re being honest) the events of the week: Donald’s earsay, Joe’s departure, Kamala’s ascension. Then, he welcomes Jessica Cale, the host of the DIRTY SEXY HISTORY podcast, to talk about her background as a novelist and historian, the castles of Wales, piracy, syphilis, medieval penitentials, the Oneida colony, the Comstock Act vis a vis Project 2025,...
Jul 26, 2024•1 hr 30 min
Tom McGrath was the editor-in-chief of Philadelphia magazine, as well as chief content officer of Metro Corp., the parent company of Philadelphia and Boston between 2010 and 2020. Under his leadership, the magazines won more than fifty awards for editorial excellence. In 2022, he was named Writer of the Year at the National City and Regional Magazine Awards. He’s written two previous books: “MTV: The Making of a Revolutio,” and, with John Basedow, “Fitness Made Simple.” He has a Substack, called...
Jul 19, 2024•1 hr 20 min
Greg Olear opens with his thoughts on Project 2025, Trump’s odd fascination with Hannibal Lecter and his bromance with Jeffrey Epstein, and the Democratic palace coup, led by Danny Ocean. Then, Greg welcomes the Ukrainian journalist Illia Ponomarenko for a discussion about the Russian invasion of Ukraine, Putin, Zelensky, and his new book, “I Will Show You How It Was: Yhe Story of Wartime Kyiv.” llia Ponomarenko is a Ukrainian journalist known as a former defense and security reporter at the Kyi...
Jul 12, 2024•1 hr 32 min
In this, the first episode of PREVAIL in three weeks, Greg Olear opens with his thoughts on the debate, the immunity ruling, the Kamala option, and the politically suicidal push to replace Biden at the top of the ticket. Then, Greg welcomes “Bad” Brad Berkwitt, a veteran who served for more than 20 years in the U.S. Navy, including 16 and a half in Naval Intelligence. After retiring from the military, he served as a government contractor for the Dept of Homeland Security. He also hosted a boxing...
Jul 05, 2024•1 hr 37 min
Billy Ray is a screenwriter and director. His writing credits include Color of Night, Captain Phillips, Richard Jewell, and The Hunger Games. He wrote and directed Shattered Glass, Breach, The Last Tycoon, and The Comey Rule. Since 2016, he’s been the messaging consigliere for the Democratic Party, helping scores of politicians and candidates with issue framing, speechwriting, debate prep, and rapid response. In this discussion, Billy Ray discusses his political “origin story” and his tips on De...
Jun 14, 2024•1 hr 15 min
