
Prevail with Greg Olear
On PREVAIL, a weekly interview podcast, the author and columnist Greg Olear discusses politics, world news, history, national security, foreign affairs, organized crime, dirty money, global corruption, and the fight for democracy with authors, journalists, academics, diplomats, researchers, and other expert guests. Every Friday.
Latest episodes

Mar 1, 2024 • 1h 30min
Feelingsball: The Leonard Leo Industrial Complex, SCOTUS Nihilism, and the Doctrine of Sad (with Dahlia Lithwick)
Greg Olear welcomes Dahlia Lithwick, senior editor at SLATE and the author of the bestseller “Lady Justice: Women, The Law, and the Battle to Save Democracy.” They discuss the current state of the Supreme Court and the impact of recent decisions; the dynamics of the court, the influence of confirmation hearings, and the changing ideologies of the justices; the need for structural court reform and the public appetite for court expansion; and the role of dark money groups in pushing cases to the court and the potential consequences of recent rulings. The conversation covers the threat to reproductive rights, the potential impact of the 14th Amendment on removing Trump from the ballot, the consequences of pardons and lack of accountability, and the rise of MAGA in Canada. Plus: a new dating app.Prevail is sponsored by BetterHelp. Get 10% off your first month at betterhelp.com/gregFollow Dahlia:https://twitter.com/DahlialithwickBuy her book:https://www.penguinrandomhouse.com/books/598207/lady-justice-by-dahlia-lithwick/Dahlia’s SLATE archive:https://slate.com/author/dahlia-lithwickSubscribe to the PREVAIL newsletter:https://gregolear.substack.com/about Opening MonologueBeginning of Interview: The Supreme Court and Order MuppetsThe Impact of SCOTUS Confirmation Hearings on Thomas, Alito, and KavanaugThe Alabama IVF DecisionThe 14th Amendment and Taking Trump off the BallotThe Rise of MAGA in Canada
Make America Great Gatsby Again!https://bookshop.org/p/books/the-great-gatsby-four-sticks-press-centennial-edition/e701221776c88f86?ean=9798985931976&next=tSubscribe to The Five 8:https://www.youtube.com/channel/UC0BRnRwe7yDZXIaF-QZfvhACheck out ROUGH BEAST, Greg’s new book:https://www.amazon.com/dp/B0D47CMX17ROUGH 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-survey.aspx?pubid=BffJOlI7qQcF&ver=short

Feb 23, 2024 • 1h 17min
Trickling Down: How the Anti-Tax Movement Hijacked America (with Michael Graetz)
In this conversation with Greg Olear, Michael Graetz discusses his book “The Power to Destroy: How the Anti-Tax Movement Hijacked America”' He explores the history and influence of the anti-tax movement, the role of race and xenophobia in shaping it, and the ideological and moral arguments behind it. Graetz also delves into the consequences of irresponsible tax cuts, the significance of taxation in American history, and the challenges of dealing with a GOP that obstructs. He highlights the need for a more nuanced understanding of taxation and the importance of addressing the growing national debt. Finally, they discuss the conservative shift of the Court, the corrupting power of money in politics, and the challenges facing American democracy. Plus: a new memory aid.Prevail is sponsored by BetterHelp. Get 10% off your first month at betterhelp.com/greg00:00: Introduction12:00: Beginning of interview.17:25: Cultural, Social, and Political Judgments Embedded in Tax Law22:09: The Influence of Libertarianism and Ayn Rand38:43: The Consequences of Irresponsible Tax Cuts57:37: The Failure of Supply-Side Economics and the Divisions in American Politics01:13:03: SCOTUS / Money as Speech in PoliticsAbout Michael Graetz:https://www.law.columbia.edu/faculty/michael-graetzBuy the book:https://press.princeton.edu/books/hardcover/9780691225548/the-power-to-destroyhttps://www.amazon.com/Power-Destroy-Antitax-Movement-Hijacked/dp/0691225540 Subscribe to the PREVAIL newsletter:https://gregolear.substack.com/aboutWould you like to tell us more about you? http://survey.podtrac.com/start-survey.aspx?pubid=BffJOlI7qQcF&ver=short
Make America Great Gatsby Again!https://bookshop.org/p/books/the-great-gatsby-four-sticks-press-centennial-edition/e701221776c88f86?ean=9798985931976&next=tSubscribe to The Five 8:https://www.youtube.com/channel/UC0BRnRwe7yDZXIaF-QZfvhACheck out ROUGH BEAST, Greg’s new book:https://www.amazon.com/dp/B0D47CMX17ROUGH 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-survey.aspx?pubid=BffJOlI7qQcF&ver=short

Feb 16, 2024 • 1h 35min
All About Leonard Leo, the Reactionary Legal Activist, Radical Catholic Zealot & Dark Money Maestro Who Captured the Supreme Court (with Tom Carter)
Tom Carter worked in Washington for years, in journalism and then in PR. For three years, he handled media relations at USCIRF, the U.S. Commission on International Religious Freedom, where his boss was one Leonard Leo, a key figure in the conservative legal movement and the capture of SCOTUS. The conversation explores the background, influence, and agenda of Leonard Leo; his management style, his use of dark money, his involvement with the Federalist Society and other organizations; his connections to Clarence Thomas and other influential figures; and the extreme radical Catholic religious beliefs that animate his opposition to abortion and LGBTQ rights. The conversation also delves into the potential ramifications of Leo's actions, his expansion into the media and entertainment industry, and the future of his influence. Overall, it highlights the danger and harm caused by Leo's agenda. Plus: Cole Porter lives!Takeaways:Leonard Leo is a key figure in the conservative legal movement and has significant influence behind the scenes.Leo's use of dark money and his web of organizations have allowed him to boost the conservative legal movement and shape the Supreme Court.His radical Catholic beliefs and agenda drive his opposition to abortion and LGBTQ rights.Leo's expansion into the media and entertainment industry through the Teneo Society raises concerns about his potential influence in these areas.The real-world ramifications of Leo's actions include the erosion of democratic principles and the harm caused to marginalized communities.00:00: Episode introduction10:43: Beginning of the interview22:37: Leonard Leo's Influence and Methods25:28: Dark Money and Leonard Leo's Organizations36:55: Relationship between Leonard Leo and Clarence Thomas47:19: The Libertarian Billionaires and Leonard Leo's Agenda52:19: The Distinction between Radical Catholicism and Mainstream Catholicism1:06:26: Leo’s networks1:17:27: The Virtually Unlimited Financial Resources of Leonard Leo1:32:16: The Danger and Harm Caused by Leonard Leo's ActionsFollow Tom:https://twitter.com/Thcarter5https://www.threads.net/@thcarter123Subscribe to the PREVAIL newsletter:https://gregolear.substack.com/aboutWould you like to tell us more about you? http://survey.podtrac.com/start-survey.aspx?pubid=BffJOlI7qQcF&ver=short
Make America Great Gatsby Again!https://bookshop.org/p/books/the-great-gatsby-four-sticks-press-centennial-edition/e701221776c88f86?ean=9798985931976&next=tSubscribe to The Five 8:https://www.youtube.com/channel/UC0BRnRwe7yDZXIaF-QZfvhACheck out ROUGH BEAST, Greg’s new book:https://www.amazon.com/dp/B0D47CMX17ROUGH 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-survey.aspx?pubid=BffJOlI7qQcF&ver=short

Jan 19, 2024 • 1h 27min
Dispatches from the Road (with Diana Spechler)
Greg Olear welcomes his friend, the novelist, essayist and travel writer Diana Spechler. They discuss the novel as an art form, writing as a profession and vocation, the allure of travel, how the U.S. is perceived abroad, the future of the country, separating art from the artist, the Stendhal effect, and more. Plus: his name is Leo.Prevail is sponsored by BetterHelp. Get 10% off your first month at betterhelp.com/gregFollow Diana:https://twitter.com/DianaSpechlerSubscribe to “Dispatches from the Road”:https://dianaspechler.substack.com/Subscribe to the PREVAIL newsletter:https://gregolear.substack.com/aboutWould you like to tell us more about you? http://survey.podtrac.com/start-survey.aspx?pubid=BffJOlI7qQcF&ver=short
Make America Great Gatsby Again!https://bookshop.org/p/books/the-great-gatsby-four-sticks-press-centennial-edition/e701221776c88f86?ean=9798985931976&next=tSubscribe to The Five 8:https://www.youtube.com/channel/UC0BRnRwe7yDZXIaF-QZfvhACheck out ROUGH BEAST, Greg’s new book:https://www.amazon.com/dp/B0D47CMX17ROUGH 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-survey.aspx?pubid=BffJOlI7qQcF&ver=short

Jan 12, 2024 • 1h 22min
Covert World War III, or, Operation Gemcrusher (with Aja Raden)
Aja Raden, author of “Stoned” and “The Truth About the Lies,” returns to PREVAIL. She updates Greg Olear about the changes coming to the diamond industry (which she foretold in the documentary “Nothing Lasts Forever”), and discusses her concerns for 2024, Elon Musk’s destruction of Twitter, contingency plans in case of Nazi takeover, lies people believe and why they believe them, the Epstein files, and her favorite Christmas movie. Plus: a new legal services firm.Subscribe to the PREVAIL newsletter:https://gregolear.substack.com/aboutWould you like to tell us more about you? http://survey.podtrac.com/start-survey.aspx?pubid=BffJOlI7qQcF&ver=short
Make America Great Gatsby Again!https://bookshop.org/p/books/the-great-gatsby-four-sticks-press-centennial-edition/e701221776c88f86?ean=9798985931976&next=tSubscribe to The Five 8:https://www.youtube.com/channel/UC0BRnRwe7yDZXIaF-QZfvhACheck out ROUGH BEAST, Greg’s new book:https://www.amazon.com/dp/B0D47CMX17ROUGH 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-survey.aspx?pubid=BffJOlI7qQcF&ver=short

Dec 29, 2023 • 1h 22min
Cheerios or Death (with Brynn Tannehill)
We know that Donald Trump is a fascist, but what would MAGA fascism look like in a second Trump term? Brynn Tannehill, senior defense analyst and author of “American Fascism” and “My Child Told Me They're Trans...What Do I Do?,” lays out the horrors to expect if Trump is sworn in in 2025. Plus: the Trump Days of Christmas.Follow Brynn:https://twitter.com/BrynnTannehillHer website:http://www.brynntannehill.com/Buy her books:https://www.amazon.com/stores/Brynn-Tannehill/author/B07MG4MCX4?ref=ap_rdr&store_ref=ap_rdr&isDramIntegrated=true&shoppingPortalEnabled=true Subscribe to the PREVAIL newsletter:https://gregolear.substack.com/aboutWould you like to tell us more about you?http://survey.podtrac.com/start-survey.aspx?pubid=BffJOlI7qQcF&ver=short
Make America Great Gatsby Again!https://bookshop.org/p/books/the-great-gatsby-four-sticks-press-centennial-edition/e701221776c88f86?ean=9798985931976&next=tSubscribe to The Five 8:https://www.youtube.com/channel/UC0BRnRwe7yDZXIaF-QZfvhACheck out ROUGH BEAST, Greg’s new book:https://www.amazon.com/dp/B0D47CMX17ROUGH 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-survey.aspx?pubid=BffJOlI7qQcF&ver=short

Dec 22, 2023 • 1h 34min
Making It in America (with Rachel Slade)
Greg Olear is joined by the journalist and editor Rachel Slade, author of the new book “Making It in America: The Almost Impossible Quest to Manufacture in the U.S.A. (and How It Got That Way).” They discuss the history of textile manufacturing in the United States, how the towns NAFTA devastated were hidden, the perils of free trade, the Gen X mindset, Prohibition trivia, all things labor movement, how and when organized crime infiltrated unions, the multiplier effect, New Americans, and what the purpose of government actually is. Plus: merry MAGA Xmas.Visit Rachel’s website:https://www.rachelslade.net/Buy her new book:https://bookshop.org/p/books/american-hoodie-the-almost-impossible-quest-to-make-things-in-twenty-first-century-america-and-how-it-got-that-way-rachel-slade/19689023?ean=9780593316887Follow her on Instagram:https://www.instagram.com/rachelmslade/Thanks HelloFresh! Go to HelloFresh.com/prevailfree and use code prevailfree for FREE breakfast for life! One breakfast item per box while subscription is active. Subscribe to the PREVAIL newsletter:https://gregolear.substack.com/aboutWould you like to tell us more about you? http://survey.podtrac.com/start-survey.aspx?pubid=BffJOlI7qQcF&ver=short. *
Make America Great Gatsby Again!https://bookshop.org/p/books/the-great-gatsby-four-sticks-press-centennial-edition/e701221776c88f86?ean=9798985931976&next=tSubscribe to The Five 8:https://www.youtube.com/channel/UC0BRnRwe7yDZXIaF-QZfvhACheck out ROUGH BEAST, Greg’s new book:https://www.amazon.com/dp/B0D47CMX17ROUGH 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-survey.aspx?pubid=BffJOlI7qQcF&ver=short

Dec 15, 2023 • 1h 10min
America/America, Lee Harvey Oswald, and the Presidential Suite at the Ritz-Carlton Moscow (with Steven Beschloss)
Greg Olear is joined by the writer, author, professor, filmmaker, and “America, America” columnist Steven Beschloss. They discuss the failure of the media to adequately cover Trump, then and now; the stakes of the next election; Lee Harvey Oswald, childhood trauma, and the making of an assassin; the importance of investing in education and why the GOP opposes it; Biden’s place in history; and the Ritz-Carlton Moscow. Plus: a new dating app.Follow Steven:https://twitter.com/StevenBeschlosshttps://post.news/@/stevenbeschlossSubscribe to “America, America”:https://america.substack.com/Watch “Media Misses”:https://america.substack.com/p/media-misses-the-wall-street-journalBuy his book:https://www.amazon.com/Gunman-His-Mother-Marguerite-Assassin-ebook/dp/B0CN518F1KThanks, HelloFresh! Go to HelloFresh.com/prevailfree and use code prevailfree for FREE breakfast for life! One breakfast item per box while subscription is active. Subscribe to the PREVAIL newsletter:https://gregolear.substack.com/aboutWould you like to tell us more about you? http://survey.podtrac.com/start-survey.aspx?pubid=BffJOlI7qQcF&ver=short. *
Make America Great Gatsby Again!https://bookshop.org/p/books/the-great-gatsby-four-sticks-press-centennial-edition/e701221776c88f86?ean=9798985931976&next=tSubscribe to The Five 8:https://www.youtube.com/channel/UC0BRnRwe7yDZXIaF-QZfvhACheck out ROUGH BEAST, Greg’s new book:https://www.amazon.com/dp/B0D47CMX17ROUGH 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-survey.aspx?pubid=BffJOlI7qQcF&ver=short

Dec 8, 2023 • 1h 17min
Red Caesar (with Will Bunch)
Greg Olear welcomes national opinion columnist Will Bunch to discuss the influence of higher education on politics, the failure of media in accurately reporting American fascism, Trump's re-election plans, the far right's dream of a Red Caesar, and the Eagles' destiny as a team.

Dec 1, 2023 • 1h 19min
Lawyers, Guns, and Money (with Jack Bryan)
We all remember the keywords of the scandal known as Iran-Contra: Oliver North, Fawn Hall, potted plant, Nicaragua, Sandinista, “I don’t recall.” The Reagan Administration was covering SOMETHING up, but what were they up to, exactly? Jack Bryan, creator of the riveting new podcast “Lawyers, Guns, and Money,” talks to Greg Olear about Iran-Contra, the Vietnam War, the mythologizing of JFK, Nicaraguan politics of the 1980s, the CIA, what Donald Trump is like in person, and more. Plus: a little Cole Porter.Follow Jack:https://twitter.com/jackabryanListen to the podcast - Lawyers, Guns, and Money:https://t.co/x5jJ5IVsdd Thanks HelloFresh! Go to HelloFresh.com/prevailfree and use code prevailfree for FREE breakfast for life! One breakfast item per box while subscription is active. Subscribe to the PREVAIL newsletter:https://gregolear.substack.com/aboutWould you like to tell us more about you? http://survey.podtrac.com/start-survey.aspx?pubid=BffJOlI7qQcF&ver=short. *
Make America Great Gatsby Again!https://bookshop.org/p/books/the-great-gatsby-four-sticks-press-centennial-edition/e701221776c88f86?ean=9798985931976&next=tSubscribe to The Five 8:https://www.youtube.com/channel/UC0BRnRwe7yDZXIaF-QZfvhACheck out ROUGH BEAST, Greg’s new book:https://www.amazon.com/dp/B0D47CMX17ROUGH 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-survey.aspx?pubid=BffJOlI7qQcF&ver=short
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