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ESPN lost a colossal figure when president and co-chairman John Skipper stepped down on Monday, with his 20 years at the network coinciding with — and presiding over — major shifts at the sports giant.

His exit came as a “massive surprise,” one ESPN insider told TheWrap, with the network and Disney, its parent company, grappling with the ongoing siege cord-cutters have inflicted on its subscriber base.

According to J.A. Adande, former ESPN analyst and current Director of Sports Journalism at Northwestern University, Skipper’s legacy will “take a while to be determined.” But the $2.66 billion per year broadcasting deal the network inked with the NBA — running through the 2024-25 season — could ultimately shape how he’s remembered in sports media.

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“It’s possible that being connected as deeply and intertwined as ESPN now is with that league, [ESPN] will benefit moving forward as we start to see perhaps the slow erosion of the NFL,” Adande told TheWrap. “The NBA just seems really well positioned to be a modern, forward-thinking, global, millennial league, and that connection with it might be the thing he leaves ESPN with in the best shape.”

That bet might be paying off, with ESPN’s NBA ratings up 18 percent to about 1.84 million viewers on average so far this year. Still, the hefty price tag the network paid for pro hoops wasn’t lost on the former employee. Added to the $1.9 billion the network shells out annually to air “Monday Night Football,” and the $700 million it spends on Major League Baseball, ESPN is paying a pretty penny to remain the go-to destination for sports.

Skipper even admitted it’s “a lot of money,” after closing the MLB deal in 2012. And those expenses have others questioning his decisions. “Overpaying for product,” according to Daniel Durbin, head of the Annenberg Institute of Sports, Media and Society at USC, was a prime example in a “series of missteps” made by ESPN in the last decade.

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“[ESPN] paid a tremendous amount for the NBA contract to lock out Fox,” Durbin told TheWrap. “This has been an era of escalating television rights for sports, where they’ve almost escalated out of sight, and part of the reason for that is people saw live sports as the last bastion of large audiences.”

ESPN’s dwindling audience, even more than keeping its competitors off its corner, was the chief reason Skipper backed up the Brinks truck for NBA action. He’d been an executive with the company since 1997, and had been president since 2012; he was there as the network reached its peak of about 100 million subscribers in 2011 — and has since seen it tumble to below 88 million customers. With highlights available on Twitter and YouTube within minutes, cord-cutting sports fans have little reason to keep ESPN beyond its slate of games. Through that prism, Skipper had no choice but to emphasize live sports.

“You need something people say they can’t live without, and people can live without some of these talk shows or news programs,” Andrew Billings, Director of the Alabama Program in Sports Communication, told TheWrap. “But if their favorite team is being shown in a game that they care about — you want to be the channel that is providing that access.

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“It’s not that the audience went away for those shows, why am I still one of the 88 million people that subscribes to ESPN?” continued Billings. “They can find the talk shows via podcasts, they can find them via radio, or other online sources. What they can’t find, and the reason they stay with ESPN, is because they’ve got the games. It’s the live sports content.”

Just last week, Skipper himself scoffed at the idea ESPN spent too much on the NBA.

“We’re in the third year of a 10 year deal for the NBA, and it is a spectacular deal with an ascendent league,” said Skipper at the Sports Video Group conference. “And let me clue you in to a little secret: we can afford it. It’s okay. We didn’t misunderstand what we were going to pay.”

Disney recently announced that “ESPN Plus,” its standalone streaming service, will launch next spring. The move will attempt to lure back fans that abandoned linear TV, but Skipper and ESPN have been criticized, most notably by ex-ESPN writer and personality Bill Simmons, for not being more proactive in addressing its shrinking audience.

“[ESPN] didn’t see a lot of this coming,” said Simmons at the Code Conference earlier this year. “They didn’t see cord cutting coming. They weren’t ready for it. A lot of decisions were made based on subs staying at a certain level. They had to realize they were a technology company. The ones winning are now Facebook, Twitter, Amazon, Hulu. ESPN should have been in that mix, but they’re in Bristol. They should have had a place in Silicon Valley. That was their biggest mistake.”

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Durbin echoed Simmons’ sentiment, believing the company was a victim of its own success.”The single biggest thing you could criticize Skipper for was not moving early and aggressively towards alternative platforms of broadcast,” said Durbin. “There was a perception at ESPN, until fairly recently, that it was bulletproof.”

All three experts agreed that more than ratings and subscriber numbers are needed to grade Skipper, however. Adande pointed to ESPN’s growth in mobile, and its booming fantasy football platform — with its “Fantasy” app pulling in 20 million users in 2017 — as a sign its business is evolving. He also mentioned the editorial decisions green-lit by Skipper, including websites FiveThirtyEight, The Undefeated, and the now-shuttered Grantland, as worthwhile risks that have since been mirrored by competitors.

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“It seems like we only talk about ESPN’s failures recently, we don’t talk about ESPN’s successes,” added Adande.

Skipper leaves ESPN a much different place than when he first stepped foot in Bristol. He was at the helm as the company struggled with the growing pains of a shift in viewing habits. But how much of that is his fault, rather than the challenges any other executive would’ve experienced, is up for debate. While the jury is still out on Skipper’s five-year run as president, his double down on live sports could be the lasting mark he leaves on his way out the door.

Tony Maglio and Jon Levine contributed to this story.

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