Jon Kelly joins Dylan to discuss Matt Murray’s surprising ascent to the WaPo executive editor job. And then Eriq Gardner swings by to weigh in on Bob Iger’s Trump settlement calculus.

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Legal analyst Jeffrey Toobin joins Dylan to scrutinize ABC News’ $15M settlement with Trump, which has everyone in the political-media industry abuzz about the signal this sends to MAGA and its adversaries. While many perceived this to be a very winnable case for ABC News, their striking decision to settle for such a high price tag has led to a myriad of questions surrounding the media climate as we head into Trump 2.0.

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Bill Cohan joins Dylan to dissect the stark financial calculus behind David Zaslav’s decision to separate Warner Bros. Discovery’s growth assets from its declining linear TV networks—a move that’s made Wall Street practically euphoric. Then they dive into Zaz’s ultimate endgame: to build, to sell, or to spin?

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Legendary media mogul and IAC chairman Barry Diller joins Dylan for a lively discussion on the shifting landscape of the media industry: Will Comcast’s spun-off cable assets thrive as a reimagined bundle or end up being sold to private equity? Do Hollywood heavyweights need greater scale to remain competitive? Can The Daily Beast transform into a powerhouse business? Then they dig into the future of the Democratic Party and Barry’s reasons for optimism in the new era of Trump and Elon.

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Former Hearst Magazines president Troy Young connects with Dylan to probe what went wrong at The Washington Post and CNN, and whether Will Lewis and Mark Thompson can fix their respective companies before the media business changes again.

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Former top CNN executive Andrew Morse joins Dylan to discuss his new career as C.E.O. of The Atlanta Journal-Constitution, where he’s applying the old NYT digital innovation playbook at the local level. Then they dig into his clashes with David Zaslav and Chris Licht, the unceremonious cancellation of CNN+, and the troubles afflicting the media landscape writ large.

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Jeremy Boreing, co-founder of the conservative media network The Daily Wire, joins Dylan to explore the surging impact of alternative media on modern politics and deliver his candid critique of legacy media's failures. Then he shares insights into the strategies driving his company’s accelerated growth and discusses what lies ahead as The Daily Wire closes in on surpassing $200 million in revenue.

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Punchbowl co-founders Jake Sherman and Anna Palmer join Dylan to discuss their vertiginous ascent from Politico all-stars to building a veritable Playbook rival. They dive into Punchbowl’s origin story, their tunnel-vision focus on Capitol Hill, the untapped potential of niche subscription markets, experimenting with A.I., and much more. 

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Jon Kelly joins Dylan to discuss the cascading effects of Brian Roberts’ monumental decision to spin off NBCUniversal’s declining cable assets. Then they get into Rachel Maddow’s $125 million contract renegotiation and how MSNBC survives without the NBC mothership.

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It’s a food media-themed doubleheader in The Grill Room! First, Dylan convenes with The Infatuation C.E.O. Paul Needham, who discusses the economics of his restaurant recommendation empire. Then acclaimed food writer and entrepreneur Alison Roman stops by to discuss her journey from legacy media to entrepreneurship and why her defenestration from The New York Times turned out to be a blessing in disguise.

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