Sports Business Journal’s Bret McCormick joins John to chart the shifting priorities in sports ownership, from media rights deals to the increased focus on real estate development. They dig into how organizations across professional leagues are leveraging real estate for steady income, touch on the myriad challenges of financing new stadiums, predict whether the Washington Commanders will return to R.F.K. Stadium, and much more.

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Michael Nathanson joins John for a rollicking conversation about the future of sports media. They dig into the R.S.N. slow bleed, CBS’s shocking cancellation of The Late Show with Stephen Colbert, ESPN’s forthcoming D.T.C. service, which potential streamers will bid on NFL rights—and much, much more.

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NASCAR commissioner Steve Phelps joins John Ourand for a candid conversation about the sport’s evolving media ecosystem, including new deals with Fox, NBC, and Amazon Prime. Phelps also outlines NASCAR’s experimental growth strategy; explains why he’s not in competition with F1 and IndyCar; and weighs in on the simmering legal standoff with Denny Hamlin and Michael Jordan—while making the case for why polarizing personalities like Hamlin are important for increasing fan engagement.

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NBC Sports’ Matthew Berry returns to the pod to share the growth story behind his fantasy sports startup, Fantasy Life. He explains how he attracted heavyweight investors like LeBron James, Maverick Carter, and Jeff Shell, and how the company has carved out a niche in an oversaturated space—boasting 1.5 million daily users and a 73 percent jump in revenue since last year. Matthew also weighs in on how leagues are adapting to fantasy and wagering—and how fantasy sports continues to reshape the relationship between fans, leagues, and gambling.

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Puck’s A.I. expert Ian Krietzberg joins John for a deep dive into the growing influence of artificial intelligence in sports. Ian discusses the promise and pitfalls of A.I. in sports, from computer vision models to predictive analytics—and stresses the importance of deploying A.I. with intent, solving real-world problems rather than embracing the technology for novelty’s sake.

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Christine Brennan, the pioneering sports columnist, joins the pod to discuss her new book, “On Her Game: Caitlin Clark and the Revolution in Women's Sports.” She unpacks the WNBA’s struggle to match the moment of Caitlin’s rise, the financial implications of Caitlin’s ascent, the league’s perpetual lack of media attention and support, and much more. Christine also reflects on her own trailblazing career pushing through sports journalism’s glass ceiling.

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Axios’s Sara Fischer returns to the pod for a sweeping tour of the most urgent issues in the sports media landscape—from the looming Trump–CBS settlement (and what a Skydance-Paramount merger portends for CBS Sports) to the College Football Playoff’s potential expansion, the growing leverage of live sports in ad markets, the possibility of a new NFL stadium in D.C., and much, much more.

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Sports Illustrated’s Jon Wertheim—America’s preeminent tennis sage—joins the pod to explore the sport’s cultural resurgence, driven in large part by breakout stars like Coco Gauff, Carlos Alcaraz, and Jannick Sinner. Jon makes a strong case for unifying the men’s and women’s tours, weighs into tennis’s global business dilemma, touches on growing interest from Saudi investors—and much, much more.

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Paul Rabil, co-founder of the Premier Lacrosse League, joins John for a deep dive into the PLL’s new five-year media rights deal with ESPN, which includes an equity stake from the network. Rabil charts the PLL’s growth trajectory, teases expansion plans, and explains why the 2028 Olympics could be a turning point for lacrosse as a global sport.

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Alexi Lalas, Fox Sports analyst and former American soccer star, swings by the pod for a wide-ranging discussion about the accelerated growth of soccer in the U.S. Alexis lays out the MLS roadmap to global relevance, celebrates the rise of the NWSL, and explains why he’s bullish on the 2026 World Cup—and what this all means for the future of the sport in the U.S.

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