Steven Cheah celebrates 10 years at Barstool Sports

Cheah didn't write a long thank-you note. He posted a montage, said it had been a ride and said he wants 10 more.

Steven Cheah

@StevenCheah

Today marks 10 years at @barstoolsports. What a ride! Looking forward to 10+ more!

A decade is a long run at a company that chews through talent and reinvents itself every couple of years. According to his LinkedIn, Cheah started in October 2016 on the business side, as Senior Director of Ad Operations. He wasn't hired to be on camera. He worked his way onto the shows the slow way, and his Barstool bio now lists him on The Yak, Fantasy Football Factory, The Bracket and The Shred Line.

Then there's the title. His bio still bills him as Barstool's VP of Football Operations, a made-up job he 'resigned' from on X in 2023 rather than face, as he put it, a scrutinous 3rd party investigation into his failures in the role. The same bio calls him a Prop Bettor Extraordinaire, claims he created fantasy football's Zero RB strategy in 2009 and says he was voted the No. 1 Buccaneers media personality in 2020. Most of that is a bit, and he commits to every word of it.

The Bucs part is real. On Wake Up Barstool on 2026-09-22, he was asked whether Baker Mayfield has already peaked. He wouldn't go there.

Wake Up Barstool

@wakeupbarstool

“I still ride for Baker. I think Baker's awesome. I'm happy we signed him to the extension.” – Steven Cheah

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That's how Cheah has lasted. He's the guy who's always around: on the morning show, on the gambling desk, on The Yak. Lately he's added SommeliCHEAH, a wine series he has grown into dozens of episodes, with guests up to and including Ryen Russillo, according to the montage.

The Stoolies were happy for him too. The replies were mostly the plain kind of congratulations you give a guy who has shown up for 10 years.

Stoolies Clubhouse 🏴‍☠️

@StooliesClub

@StevenCheah @barstoolsports Atta boy Cheah! Keep up the good shit!

Cheah got here by grinding, starting in ad ops and working his way onto half the shows on the network. He says he's looking forward to 10 more. Odds are he'll still be backing Baker and losing Woody Marks bets when he gets there.