John Skipper Credit: The Dan Le Batard Show with Stugotz on YouTube

John Skipper departed ESPN before it had to confront a future when it was no longer a cable cash cow. But he believes ESPN tying itself to sports betting was an inevitable part of that evolution, even if Penn National Gaming makes for an imperfect partner.

In an episode of The Sporting Class from Meadowlark Media released last week, Skipper explained why ESPN faces an “uphill battle” in partnering with Penn, which Skipper called an “also-ran” in the gambling space.

“I do think ESPN faces an uphill battle,” Skipper explained. “They are aligned now with Penn Bet, which I believe is an also-ran in this. Penn has a very profitable business, but I think they’re a 2 percent (market share) in the sports (betting) business.”

But with ESPN targeting a full streaming product by 2025 and cable carriage fees no longer supporting massive profits, Skipper understands the deal.

“I’m also not surprised to see ESPN do this,” he said. “In the space of the declining pay-TV universe, they have to look for ways to cut expenses, they have to look for other ways to make money. They’re exploring here whether they can make money this way. It seems like good business to me.”

Skipper, a longtime supporter of ESPN The Magazine and the network’s journalistic work, does not see a gambling partnership as a killshot to ESPN’s credibility.

“I don’t personally believe it’s an unmanageable conflict for ESPN,” Skipper explained. “They have to make it clear, and they will, to their journalists that they have to have a wall between (ESPN Bet) and what they do. I think that will happen, overwhelmingly.”

“The idea that ESPN would engage in ‘oh, let’s put out that someone might be injured and we’ll benefit from the line on that from our association with Penn,’ it’s just ridiculous.”

Some would say Skipper could have helped ESPN get in on the ground floor of the massive gambling industry. By the time he left the worldwide leader in late 2017, legal proceedings were underway that ultimately say the U.S. Supreme Court legalize sports betting at the national level. Daily fantasy sports products were extremely popular already.

Instead, ESPN and Disney held out until the biggest operators had already begun massive marketing and content licensing spending sprees. They are now paying the price.

[The Dan Le Batard Show with Stugotz on YouTube]

About Brendon Kleen

Brendon is a Media Commentary staff writer at Awful Announcing. He has also covered basketball and sports business at Front Office Sports, SB Nation, Uproxx and more.