Eriq Gardner joins Dylan to dissect the wave of MAGA-driven lawsuits targeting Trump’s media adversaries. Eriq highlights casino magnate Steve Wynn’s efforts to revive his 2018 defamation suit against the Associated Press, which he hopes is elevated to the Supreme Court, potentially setting the stage for a SCOTUS showdown that could challenge the landmark ‘Times v. Sullivan’ ruling. The duo debate whether a better legal framework exists and suggest how media organizations can navigate these shifting legal battlegrounds.

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Former Hearst Magazines president Troy Young rejoins Dylan for a deep dive into the seismic impact of A.I. on media. He breaks down how A.I. has accelerated the decline of certain media businesses, stresses the urgent need for stronger I.P. protections, and unpacks the high-stakes challenges—and untapped opportunities—legacy brands face in an A.I.-driven future.

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In this exclusive bonus episode of The Grill Room, Jon Kelly joins Dylan to tackle a handful of hot button topics shaping the media industry: the hunger screams at CBS News, the baffling corporate embrace of Trump 2.0., and Fox News’s continued march into mainstream. They also discuss how storied print publications like ‘The Atlantic’ and ‘The New Yorker’ can future proof their businesses in the age of A.I.

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Emily Sundberg, creator of Feed Me, joins Dylan for an in-depth look at her meteoric rise as an independent Substacker. Having amassed 60,000 subscribers—and counting—Emily shares how authenticity, adaptability, and audience engagement have fueled her success. She also discusses self-funding her company without outside financing, the potential risks of a fully decentralized media landscape, and her plans to expand beyond Substack while leveraging her growing platform.

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'The New Yorker' editor David Remnick joins Dylan to reflect on his nearly three-decade tenure as the magazine marks its 100th anniversary. He delves into the evolution of the magazine industry over the years, an inside look at sustaining The New Yorker’s unparalleled loyal subscriber base, and how the publication has uniquely blended serious journalism with humor. David also touches on the challenges of navigating the advent of A.I., and how the company is planning for the future

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The Atlantic’s C.E.O. Nick Thompson joins Dylan for a candid conversation about the existential challenges of leading a media company, centered around the looming threats and opportunities of A.I. Nick envisions a media ecosystem where their web presence goes away, and lays out his growth strategy to mitigate the concerns: building the strongest possible direct relationships with readers while cutting out reliance on tech platforms altogether.

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NBC News vet and former Meet the Press anchor Chuck Todd joins Dylan for a candid conversation about his departure from the network after nearly two decades. He reflects on the decline of media trust, the urgent need to revitalize local journalism, and how the internet has reshaped news consumption. Chuck also scrutinizes the nationalization of politics before the duo switch gears to explore the potential for podcasts to evolve into dynamic, multi-hour programming, à la ESPN’s signature daytime shows.

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MSNBC’s Chris Hayes joins Dylan for a thrilling and sobering deep dive into how social media and smartphones hijacked our brains; how attention became the single most powerful currency in the political economy; and why Donald Trump is singularly effective at commanding it.

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John Ourand joins Dylan for an insider’s look at how the NFL is preparing for the upcoming Super Bowl in New Orleans—and whether the league is feeling the effects of small-market Chiefs fatigue. The duo also delve into the crucial role of live sports rights in keeping media businesses afloat, and explore how streaming giants like Amazon and Netflix are reshaping the future of sports broadcasting.

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The New York Times’ Ben Mullin joins Dylan for a deep dive into Mark Thompson’s attempt to transform CNN from a cable television network into a digital and streaming juggernaut. After a round of mass layoffs, the duo contemplate whether CNN as a digital-first enterprise can maintain the network’s influence in a post-linear landscape, and whether Thompson actually has a plan to get there.

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