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The Former ESPN Boss Behind ’30 for 30’ Is Ready to Get Political Under Apple TV+ Deal

John Skipper and Dan Le Batard’s Meadowlark Media wants to lean into social issues and making money.

Meadowlark Media Founders John Skipper and Dan Le Batard

Meadowlark Media Founders John Skipper and Dan Le Batard

John Skipper/Getty

When former ESPN president John Skipper greenlit Bill Simmons’ and Connor Schell’s award-winning “30 for 30” documentary series, he also built the template for his new company, Meadowlark Media: Great content that may or may not be about sports, but is never afraid to show its politics.

“We have credibility in sports, so you use that credibility to get started,” Skipper said before boarding an airplane traveling south-by-southwest to SXSW. There, he and former ESPN host-turned-Meadowlark partner Dan Le Batard will tape leading sports podcast “The Dan Le Batard Show with Stugotz” March 13 and 14 (from 3-5:30 p.m. CT) with a live studio audience at Austin’s Four Seasons Hotel. Le Batard is also hosting a conversation at SXSW’s Athlete Empowerment Summit with Ricky Williams, the 1998 Heisman Trophy winner who now does astrology readings on the podcast.

Skipper said he roots for artists as hard as he roots for athletes. “I don’t think it’s going to be difficult for us to expand our offerings outside of sports,” he said. “I have not encountered the least bit of resistance.”

In a few years, half or more of Meadowlark’s output may not even be sports adjacent, Skipper told us. The president of ESPN from 2012-2017 (and executive VP of its content portfolio before that) is unconcerned about being boxed in by his and Le Batard’s shared area of expertise. This is a whole new world, especially in the streaming arena, where Meadowlark has a multiyear, first-look deal at Apple TV+.

Skipper has gotten away with telling human stories under the guise of sports for decades, culminating with ESPN’s critically lauded “30 for 30” series. Among the films under that banner we discussed during our conversation included “O.J.: Made in America” (really “about race and social justice in the United States”) and “Once Brothers” (as Skipper puts it: “a story about friendship and ethnic cleansing”).

OJ: Made In America

O.J. Simpson archival photo in 30 for 30 film “O.J.: Made in America”

ESPN

Skipper’s ESPN tenure only ended after he left to seek treatment for substance abuse (Skipper has said a cocaine dealer attempted to extort him). People take his calls and Le Batard’s massive following — “The Dan Le Batard Show with Stugotz” averages more than 3 million downloads per week — keeps them listening on the other end.

The 66-year-old skipper of Meadowlark — which is named for the bird that sings while it flies, as well as for former Harlem Globetrotters star Meadowlark Lemon — believes non-live-event sports content is “underrepresented” on streaming services like Apple’s, which this week signed a deal to live-stream Major League Baseball games on Friday nights.

Skipper is out to widen that scope and be profitable doing it. “This is a little bit old-fashioned,” he said. “We’re creating a company that’s going to make money.”

Meadowlark Media's hit podcast "The Dan Le Batard Show with Stugotz"

Meadowlark Media’s hit podcast “The Dan Le Batard Show with Stugotz”

Meadowlark Media/YouTube

The SXSW road show is more than stunt programming that complements Dan’s speaking arrangements; Skipper described it as the first step of a very purposeful plan. “Dan has always been very proud of being a Hispanic journalist from Miami who has a national voice,” he said. “We want to expand upon that, get Dan out to other places, let Dan be comfortable talking about social issues and being who he is.”

In Le Batard, Skipper’s cofounder and former employee has a kindred, fellow-progressive spirit. Skipper said one of Le Batard’s “issues” at ESPN was the Disney-owned company’s notion that “you’ve got to keep the politics out of sports.”

“Neither Dan nor I believe that,” said Skipper, who lunges hard to the left politically, as does Le Batard. “Sports is the greatest way in the world to tell stories about people and racial injustice and friendship and courage and inspiration.”

In that way, Meadowlark is the anti-ESPN.

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