On the last day of Dan Le Batard’s ESPN radio show in January, John Skipper flew to Miami to watch from a studio inside South Beach’s Clevelander hotel. Skipper, the former president of ESPN, knew the place, and the people, well: He’d had the studio built to give ESPN a physical outpost in Miami, which he viewed as crucial to increasing Hispanic viewership. Le Batard, the son of Cuban exiles whom Skipper brought to the network, recorded his radio and TV shows there. “A janitor’s closet in a South Beach hotel,” Le Batard called it.

But Skipper had left ESPN in 2017, after an incident involving cocaine and an alleged extortion attempt. And Le Batard’s relationship with ESPN had deteriorated in the years since, with the host pushing to inject more politics into his shows, until the sides announced a split late last year.

Skipper viewed the trip as an act of reciprocation. Four years earlier, Le Batard had traveled to rural North Carolina to visit Skipper in his hometown after his tumultuous exit from ESPN. They went to closed furniture factories that Skipper had grown up around and listened to old records, and Skipper introduced Le Batard to his mother.

Now, Skipper wanted to be there for Le Batard in his moment of transition. But there was also business to discuss: Skipper and Le Batard had plans for a new company. After Le Batard signed off, Skipper addressed him and his small team of producers — the “pirate ship,” as they call themselves — and promised them life after ESPN.

“We looked around and said: ‘Wow, really? This is going to be a new media company?’ ” Skipper said in a recent interview. “But it was a rallying cry, too, that everybody was going to come along.”

Soon after that day in Miami, Skipper and Le Batard announced Meadowlark, which can be hard to define for even the men who founded it. Part media company and part production company, it doesn’t plan to hire many employees. But it does want to make content, mostly about sports, by a group of Le Batard’s friends and collaborators: podcasts, documentaries, scripted shows and more. Then it wants Skipper to sell that content to the growing list of platforms competing in the new streaming economy.

Skipper ticked off the companies spending big in their quest for consumers’ attention: Netflix, he said, will soon be spending $23 billion per year on content; Apple, he said, is going to spend $6 billion; Disney will have a budget between $15 billion and $20 billion.

“There is a moment in time,” he said, “which is right now, where there is going to be more money spent on content than it’s ever been in history.”

Meadowlark’s first big sale was announced late last month: a three-year, $50 million deal with DraftKings. (The gambling company will distribute and promote itself on Le Batard’s show; Meadowlark will develop content for the gambling company.) The deal means Le Batard and Skipper, like much of sports media these days, have found they are most valuable, at least right now, if they can turn their audience into bettors.

But Skipper, 65, and Le Batard, 52, have loftier pursuits, and to fulfill them, they have turned to each other. For Le Batard, Meadowlark is a test of what he can be without ESPN’s platform. For Skipper, it’s the chance at one big final act of his career. And for the two of them, it’s about whether, together, they can deliver for each other the post-ESPN life they both want.

Filling a void

It may be easier to explain what Meadowlark isn’t going to do.

“We are not going to do the sports version of ’90 Day Fiancé,’” Skipper said.

The same is true of his deal with DraftKings, he said.

“Barstool is driving value,” Skipper said, referencing gambling operator Penn National buying a stake in the controversial sports media company. “I don’t think it means you have to do reprehensible, misogynist content. If somebody came to me and said: ‘I’ll give you a really high margin; you’ve got to do a show on the sexiest pictures of cheerleaders you can find. Can you find pictures of cheerleaders where they jump up and down and their panties are up in their butts? Can you find that for me? I’ll pay you a bunch of money.’ The answer’s no, I won’t do that.”

Skipper was wearing a maroon sweater, circle-rimmed glasses and khakis rolled up to reveal blue suede shoes, his apartment’s floor-to-ceiling windows offering a view of the Hudson River. He was sprawled in front of a coffee table designed, Skipper pointed out, by French painter Yves Klein. The tabletop was a clear acrylic box filled with mounds of raw pigment. You have to buy them from his studio and they come in and they pour in the pigment,” Skipper said. “Cobalt blue.” (A new table goes for $21,000.)

He has lived here since early 2019, moving in after he resigned from ESPN, which he did over what he called an attempted extortion attempt from someone he bought drugs from. Skipper declined to elaborate on his ESPN exit, saying only that he has moved past his personal issues and they never affected his work. After ESPN, he spent two years as the global chairman of DAZN, a streaming service that offered a chance to rebound and a tasty narrative: former ESPN president joins upstart to take on his former company in the live sports rights business.

But it didn’t work out that way. DAZN has had some success as a disrupter in Europe and Japan, but its American pursuits, including several high-profile boxing deals, have mostly fizzled.

With Meadowlark, Skipper is back with his first love: storytelling. He worked with famed publisher Jann Wenner at Rolling Stone before climbing the ladder at ESPN, helping launch ESPN the Magazine and greenlighting Grantland, Bill Simmons’s since-shuttered online magazine, and the acclaimed “30 for 30” documentary series. His supporters speak in reverence for how he empowered the voices of minorities and journalists such as Le Batard.

“I infiltrated ESPN.com with book and magazine techniques — writers and aesthetics and photography,” Skipper said, ticking off writers he hired, including Jemele Hill (now a Meadowlark adviser) and Wright Thompson (ESPN’s best-known magazine writer). “And I went and infiltrated television with all of these people.”

Now he’s watching as ESPN pulls back from some of that, laying off many journalists and shutting down the magazine. (Meadowlark hired Gary Hoenig, a former editor-in-chief of the magazine, as its executive editor.)

Skipper said Meadowlark won’t compete with ESPN, a sprawling behemoth with more live sports rights than ever, but the network’s direction leaves an opening. “I don’t think they will abandon journalism,” he said. “But the scale will be less.”

A crisis and a bond

As Skipper ascended ESPN’s corporate ladder, he looked around and noticed most of the company’s prominent voices were White. In the 1990s, he recruited Le Batard, a former Miami Herald columnist, to write for the magazine, and Skipper spent the next decade trying to get him on TV. In 2011, he succeeded, offering Le Batard a TV show that allowed his father to appear on the air and his brother to do the artwork in the studio.

Le Batard’s radio show later joined ESPN’s national lineup, and he became one of ESPN’s most recognizable personalities — a kind of anti-Mike Francesa, the bombastic host of New York’s WFAN. Le Batard poked fun at the seriousness of sports, once giving his baseball Hall of Fame ballot to Deadspin and paying for billboards that mocked LeBron James leaving Miami for Cleveland, forcing Skipper to suspend him.

Le Batard’s shows also became an incubator for young ESPN talent, including Bomani Jones, Pablo Torre and Mina Kimes. Le Batard believed Skipper empowered him to help fulfill his mission to make ESPN more diverse. “The smartest on-air talent at ESPN would gravitate toward us,” Le Batard said.

The day Skipper left ESPN, Le Batard cried on the air, then took off for North Carolina.

“Someone I cared about, someone who had done a lot for me, was in pain,” Le Batard said. “That’s when we became legitimate friends.”

Le Batard said he had full confidence in Skipper to lead the new company, despite his messy exit from ESPN. “I couldn’t speak to whatever was happening in his life that led to that stuff,” he said. “But this is the happiest I’ve seen him.”

With Skipper gone from ESPN, Le Batard clashed with the network’s new leadership, including after supporters at a rally for President Donald Trump chanted “Send her back!” about Somali-born Rep. Ilhan Omar (D-Minn.). ESPN’s new president, Jimmy Pitaro, wanted politics discussed strictly through a sports lens; Le Batard called that “cowardly” and accused the network of “not having the stomach for the fight.”

Le Batard said Skipper hired him to be the country’s leading Hispanic sports voice, with an obligation to speak for immigrants even if that made executives uncomfortable.

“A lot of things changed in this country over the last four years,” Le Batard said. “But I didn’t change.”

It wasn’t just politics, though. ESPN shaved an hour off Le Batard’s radio show and, as part of companywide layoffs, cut one of his producers. Le Batard declared on the air that he would hire him back, paying the salary out of his own pocket. That led to buyout discussions. As part of the separation agreement, Le Batard took his podcast audience feeds with him, allowing his subscribers to follow him wherever he landed.

Le Batard today likes to talk about his newfound freedom. With his podcast off of ESPN, he devoted ample time to discussing the Jan. 6 riot at the Capitol. For Skipper, there is a similar feeling. Early in the Trump administration, when Hill, then a “SportsCenter” anchor, ran afoul of the network by calling Trump a white supremacist on Twitter, it was Skipper who called her into his office to scold her. “It turns out she was right,” Skipper said.

‘High and low’

In February 2020, audio streaming giant Spotify paid around $250 million to acquire the Ringer, built by Bill Simmons after he left ESPN, his contract not renewed by Skipper. In discussing Meadowlark, Skipper mentioned the Ringer’s success. So did one of Meadowlark’s investors.

“I looked at the Ringer valuation,” said Eric Jackson, who invested. “Meadowlark has Le Batard, and I think of him as the anchor in the way that [Bill] Simmons was the anchor.”

But the Ringer was a start-up that launched a popular podcast network ahead of a digital audio boom. It has a large team of employees and around 40 podcasts in its network today. Simmons is also better known than Le Batard outside sports media.

Skipper, meanwhile, wants to hire a lean business development staff and a small number of content-focused employees who will receive a salary and share profits in what they create. Much of the company’s work will be done on a project basis with journalists or filmmakers who arrive with show or documentary ideas. Skipper will sell those ideas, he says, leveraging his executive-level relationships and hopefully making deals to sell multiple projects at once to, say, Apple or Netflix. As models, he cites Pixar or Ron Howard’s Imagine Entertainment.

Meadowlark has announced a few big-name advisers, including Hill and “Parks and Recreation” creator Mike Schur. According to a person with knowledge of the discussions, it also has considered collaborations with Kate Fagan, formerly of ESPN; Roger Bennett, half of the soccer podcast turned TV show “Men in Blazers”; and ESPN’s Jones.

So far, Le Batard’s show, funded and distributed by DraftKings, is the only sure thing. As for hints at what other content might look like, Skipper cited the “30 for 30” model of hiring directors and empowering them to tell their stories. On his radio show, Le Batard has aired a recurring bit — director Adam McKay plays a fictional, no-politics-just-sports shock jock who mounts a campaign for Congress — that could become something bigger.

“This is one of those deals you’ll know how to answer that question of what it is three years from now,” Schur said. “It will be defined by what they did, not some mission statement.”

Whether it will work is another question. Inside ESPN, there was a belief that while Le Batard’s podcast was popular, its brand of humor didn’t translate to terrestrial radio. (In the same time slot, Mike Greenberg’s show has added radio affiliates since replacing it.) That may not matter in an on-demand world, where Le Batard’s devoted following may be more valuable than ratings points.

Skipper has his own history of hits and misses. He was the first executive to see the promise of global soccer, making the World Cup an event and putting the English Premier League on TV, and he created the Undefeated, the ESPN website that covers race and sports and has become more prominent amid the country’s racial reckoning. But he also championed a doomed evening “SportsCenter” and an ill-fated attempt to partner with Barstool. At DAZN, his biggest original content play was an expensive baseball show that, while charming, didn’t break through.

Meadowlark’s success will rest on Skipper and Le Batard, making and selling. But the two also will get to define their own success.

“He’s trying to monetize a hugely interesting dinner party,” Le Batard said of Skipper. “But it’s the dinner party he wants to be at.”

Back in his apartment, Skipper looked up at his sprawling bookcase. He is reading “Bunk,” a book about a post-fact world.

“I’ve got a spartan existence with everything I love,” he said. “I’ve got my books, and I’ve got my music.” He nodded at his record player next to the bookshelf.

What about sports? After a pause, Skipper said he liked European football, too.

Le Batard said: “Skipper is a learned man. He is an intellectual. And we have Stugotz,” a reference to his often sophomoric co-host. “We will do high and low and cast a wide net.”