Jon Kelly joins Dylan to ruminate on a handful of developments across the media landscape: Will Lewis’s fantasy subscriber number for The Washington Post; Emma Tucker’s stalwart leadership at The Wall Street Journal; the latest on Mark Thompson’s CNN digital transformation strategy; and the impending A.I. newsroom revolution. To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

Ian Orefice, founder of EverWonder Studio and former TIME Studios president, joins Dylan to dig into how live sports has become the next front in the streaming wars. Then they kibitz about EverWonder’s role in producing the record-breaking Netflix Christmas NFL games and whether the Tyson vs. Paul fight represents the future of sports media rights battles to come. To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

Ben Smith, co-founder and editor-in-chief of Semafor, dives into the media landscape's shifting dynamics as 2025 approaches. He discusses the challenges news organizations face with Trump's potential return and the implications of recent talent departures at The Washington Post. Smith also explores the rising significance of newsletters in media distribution and the innovative fusion of events and journalism, highlighting how these changes affect audience engagement and adapt to evolving political climates.

In this discussion, Troy Young, former Hearst Magazine president, shares his insights on the future of the media industry. He emphasizes the transformative role of A.I. in changing how news is consumed and the urgent need for media companies to adapt to shifting consumer behaviors. The conversation also explores the blending of traditional and modern media, the challenges of maintaining authenticity, and the evolving landscape shaped by new platforms. Young highlights the importance of innovation to ensure relevancy in a rapidly changing environment.

Join political commentator John Heilemann as he unpacks the tumultuous year in media. Heilemann discusses the unsettling alliance between tech giants and Trump, alongside Jeff Bezos's challenges at The Washington Post. He highlights the shifting media landscape, particularly the rise of podcasting, as a dominant force in political discourse and the complex dynamics of audience engagement. The conversation also critiques the media's accountability and the twisted power of platforms like X, making 2024 a pivotal year in the industry's evolution.

David Axelrod, a renowned Democratic strategist and CNN commentator, shares his insights on the evolution of podcasting and its impact on politics and culture. He humorously recounts the early days of his podcasting journey and emphasizes the power of authentic conversations in a digital age. Axelrod also discusses the challenges of navigating political discourse during the Trump era and highlights the importance of genuine engagement over traditional media formats. With a nod to jazz improvisation, he connects spontaneity to the art of crafting compelling dialogues.

Jon Kelly, co-founder and editor of Puck, analyzes the surprising appointment of Matt Murray as executive editor of The Washington Post and the impact on media leadership dynamics. Eric Gardner, Puck's legal expert, weighs in on Bob Iger's recent settlement concerning media ethics and its broader implications amid industry challenges. They explore the disconnect between executive compensation and viewership, along with the complexities surrounding libel settlements, highlighting the ongoing evolution of journalism and corporate behavior.

Legal analyst Jeffrey Toobin delves into ABC News’ shocking $15 million settlement with Trump, raising eyebrows across the media landscape. He discusses the potential chilling effects this decision may have on press freedom and the daunting pressures journalists face. Toobin further analyzes how such settlements could reshape defamation law and the integrity of reporting, all against the backdrop of growing political influence and the chilling concept of 'anticipatory obedience' among media organizations. A must-listen for anyone concerned about the future of journalism!

Bill Cohan, a seasoned financial journalist and author, joins Dylan to unpack David Zaslav’s bold move to separate Warner Bros. Discovery’s growth assets from its wavering linear TV networks. They explore the euphoric response from Wall Street and delve into Zaz’s strategic intentions: build, sell, or spin-off? The discussion touches on CNN's financial future, the shifting media landscape, and the implications of corporate restructuring in a rapidly evolving environment.

Barry Diller, a legendary media mogul and the chairman of IAC and Expedia, joins Dylan for a dynamic conversation about the shifting media landscape. They discuss the future of Comcast's cable assets and whether they'll find success as a reimagined bundle. The pair dives into The Daily Beast's potential evolution into a business powerhouse. Barry also shares his optimistic outlook on the Democratic Party’s future amid the challenges posed by Trump and Elon Musk, offering a fresh perspective on resilience in the industry.