Bill Simmons

If it takes CEO Bob Iger noticing his children love sports gambling in order for Disney and ESPN to finally embrace a cash cow in sports, it’s probably too late to own that sector of the business. At least that’s how longtime gambling aficionado Bill Simmons sees his former employer’s delayed foray into betting.

Discussing ESPN’s recent partnership with Penn Entertainment on its ESPN Bet app and content vertical on the latest episode of Sports Illustrated Media, Simmons explained how ESPN waiting too long to embrace betting allowed them to be overtaken by the likes of Pat McAfee and Barstool Sports among many sports fans.

“They should have been in the forefront,” Simmons told host Jimmy Traina. “They should have bought DraftKings. They should have been on the ground floor. They’re way late, and I really think they’ve handled it badly.”

Simmons referenced a story in which it was reported Iger only instructed ESPN president Jimmy Pitaro to invest in wagering after Iger noticed his children betting on sports all the time.

Simmons also discussed how during his time as a writer at ESPN, he was dissuaded from covering gambling lines and his own wagers. ESPN editors told him to tone down his references to gambling while covering sports.

In fact, when he first started at ESPN, Simmons said he was discouraged from even mentioning fantasy football. ESPN editors saw fantasy as “Dungeons and Dragons ****” according to Simmons.

“They eventually caught up,” Simmons acknowledged.

Today, betting and fantasy are inescapable in sports coverage. The Ringer, which Simmons founded, has a licensing deal with FanDuel for live sports shows. Nearly every network or start-up has a sponsorship deal.

ESPN’s deal with Penn may be too little, too late.

[SI Media with Jimmy Traina]

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.