Prevail with Greg Olear

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, the history of abortion, and more. Plus: the safety is off.

Jessica Cale is the host of Dirty Sexy History, a podcast that looks beyond the sanitized and the idealized to the dirty reality of human history. She’s the author of ten works of historical fiction, including the Southwark Saga, and numerous nonfiction pieces. She earned degrees in Ancient History, Medieval Studies, and Creative and Media Writing at Swansea University while climbing castles and photographing mines for BBC History magazine. She appears in Netflix’s The Lost Pirate Kingdom.

Follow Jessica:

https://x.com/DrtySexyHistory

Listen to DIRTY SEXY HISTORY:

https://podcasts.apple.com/us/podcast/dirty-sexy-history/id1568066159

About her podcast:
https://dirtysexyhistory.com/welcome/

Buy her books:
https://www.amazon.com/stores/author/B00PVDV9EW/

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

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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 Common Good. His new book is “Triumph of the Yuppies: America, the Eighties, and the Creation of an Unequal Nation.”

Greg Olear talks to Tom about his new book, the Yuppie movement and what it portended to the country, Ronald Reagan and Jack Welch, and nostalgia. In the second half, they talk about how the media is broken, how it might be fixed, and how Gen Z could be just the folks to do so. Plus: media songs!

Prevail is sponsored by BetterHelp. Get 10% off your first month at betterhelp.com/greg

Follow Tom:
https://x.com/tmcgrathphilly

Buy his book:
https://www.amazon.com/Triumph-Yuppies-America-Eighties-Creation/dp/1538725991

Check out his Substack:
https://tmcgrath.substack.com/

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

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-survey.aspx?pubid=BffJOlI7qQcF&ver=short

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 Kyiv Post and subsequently a co-founder of the Kyiv Independent. He has covered the war in eastern Ukraine since the conflict's earliest days, as well as Russia's full-scale invasion of Ukraine since 2022. He has also had deployments to Palestine and the Democratic Republic of the Congo as an embedded reporter with UN peacekeeping forces. Ponomarenkowon the Alfred Friendly Press Partners fellowship and was selected to work as USA Today's guest reporter at the U.S. Department of Defense. He lives in Bucha outside Kyiv.

Plus: dictator disco!

Prevail is sponsored by BetterHelp. Get 10% off your first month at betterhelp.com/greg

Follow Illia:
https://x.com/IAPonomarenko

Buy his book:
 https://www.amazon.com/Will-Show-You-How-Was/dp/1639733876

Subscribe to The Five 8:

https://www.youtube.com/channel/UC0BRnRwe7yDZXIaF-QZfvhA

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-survey.aspx?pubid=BffJOlI7qQcF&ver=short

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 show, Ringside Reporter. And he’s now the host of the Bad Brad Berkwitt Show, where he interviews key figures in the fight for democracy. In this conversation, Greg talks to Brad about his career, intelligence services, the Gulf War, Gitmo, and how to take on MAGA. Plus: a new executive search firm!

Follow “Bad” Brad:
https://x.com/BadBradRSR

Watch his show:
https://www.youtube.com/@TheBadBradBerkwittShow

Thanks AURA. Go to  AURA.com/PROTECTION for a 14 day trial plus a check of your data to see if your personal information has been leaked online, all for FREE.

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-survey.aspx?pubid=BffJOlI7qQcF&ver=short

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 Democratic Party messaging, reveals the secret to communicating with conservatives, and lauds the achievements of President Biden. They talk about reproductive rights, the Supreme Court, the 2024, how the Dems should frame trump’s criminality, and more. Plus: the Sam Alito blues.

Follow Billy:
https://x.com/BillyRay5229

Thanks AURA. Go to  AURA.com/PROTECTION for a 14 day trial plus a check of your data to see if your personal information has been leaked online, all for FREE.

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-survey.aspx?pubid=BffJOlI7qQcF&ver=short

This week, Greg Olear shares 34 thoughts on 34 felony counts. Then, there is a reprise of the May 31 episode of “The Five 8,” in which Greg and LB try, and fail, to remember all of Donald’s crimes. Plus: blowing!

Subscribe to The Five 8:
https://www.youtube.com/channel/UC0BRnRwe7yDZXIaF-QZfvhA

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-survey.aspx?pubid=BffJOlI7qQcF&ver=short

Jason Pack is the Founder of Libya-Analysis LLC, and the co-host of Disorder, a geopolitics podcast co-produced with Goalhanger Podcasts. He is a Senior Analyst for Emerging Challenges at the NATO Defence College Foundation in Rome. In partnership with NDCF, Jason leads a project entitled NATO and the Global Enduring Disorder, which produces a range of content (including the Disorder podcast and series of publications) attempting to sketch out a ‘unified field theory’ of our current era of geopolitics while proposing actionable solutions to our most pressing collective action challenges. His most recent book, Libya and the Global Enduring Disorder (Hurst, Oxford University Press) is a ‘cross-over’ academic book that explores what Libya’s dysfunctional economic structures and its ongoing civil war reveal about our era of 21st-century geopolitics. Jason’s concept – that we no longer inhabit the post-Cold War World, but have entered a new era – the ‘Enduring Disorder’ – was conceived to describe the collective action failures that have come to define international politics.

In this discussion, Jason Pack talks to Greg Olear about the death of Raisi in Iran, the situation in Ukraine, Biden’s policy in Gaza, and why a Labor victory in the UK elections would be good for Joe Biden. Plus: a Republican Party game!

Listen to the DISORDER podcast:

https://linktr.ee/disorderpod

More about jason:

https://www.jasonpack.org/

Check out ROUGH BEAST, Greg’s new book:

https://www.amazon.com/dp/B0D47CMX17

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-survey.aspx?pubid=BffJOlI7qQcF&ver=short

In this special “Rough Beast” book launch episode, the PREVAIL podcast is turned upside-down: Greg Olear is the guest, and the host is his wife, Stephanie St. John Olear. They talk about the new book, confirmation bias, and Biden’s chances of winning in November. Plus: Scar-Jo!

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-survey.aspx?pubid=BffJOlI7qQcF&ver=short

Alessandra is an Italian journalist and political commentator who goes by the pen name Alias Vaughn. She’s been helping me understand the global political landscape—including what’s happening right here in the US—for going on eight years now.

In this conversation, Greg Olear interviews Alessandra about her background and her interest in US politics. They discuss JFK’s policy towards South America, with Alessandra sharing her research on the topic; the current political situation in Italy, including the prime minister and her stance on various issues; the public opinion of Trump in Italy; the similarities between Trump and Mussolini, and much more. Plus: a both sides superhero! 

Follow Alessandra:

https://twitter.com/aliasvaughn

Check out ROUGH BEAST, Greg’s new book:

https://www.amazon.com/dp/B0D47CMX17

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-survey.aspx?pubid=BffJOlI7qQcF&ver=short

Jenny Cohn is an attorney, election integrity advocate, and political writer whose articles have appeared in the New York Review of Books, Who What Why, The Independent, Salon, and the Bucks County Beacon. She now covers the Christian right at her Substack, the Christian Right Observer Weekly, or CROW.

Cohn talks to Greg Olear about her work on election integrity and the Christian right; her new project, the Christian Right Observer Weekly, and the collaboration with researcher Kira Resistance; the influence of Leonard Leo, a fundamentalist Catholic activist, on the Supreme Court; rightwing efforts to make abortion illegal on a federal level, the Christian right's opposition to LGBTQ rights and contraception, and their goal to undo the sexual revolution; the unholy alliance between religious and economic freedom Republicans; and fetal personhood and the right’s coming assault on women’s health. Plus: a little Elvis.

Follow Jenny:

https://twitter.com/jennycohn1

Subscribe to her Substack:

https://crownewsletter.substack.com/

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-survey.aspx?pubid=BffJOlI7qQcF&ver=short