Prevail with Greg Olear 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.

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!

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!

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!

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.

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!

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