Polymarket reeled in LeBron James for a partnership that, according to Front Office Sports, is worth $15 million per year. James is far from the only celebrity endorsing the controversial prediction market (to put it mildly).
Skip Bayless and Shannon Sharpe didn’t get the invite to James’s much-maligned Polymarket ad, but the former Undisputed debate partners reunited for their own commercial.
“With the legend @RealSkipBayless. Miss you my brotha!” Sharpe posted on X on Friday. “On set for our new @Polymarket commercial airing soon. More news coming soon [shushing emoji].”
Bayless reposted that, writing, “Miss you too, man! Great seeing you—can’t wait for everyone to see what’s coming.”
With the legend @RealSkipBayless. Miss you my brotha!
On set for our new @Polymarket commercial airing soon. More news coming soon 🤫 pic.twitter.com/1YlpgHN75E
— shannon sharpe (@ShannonSharpe) September 25, 2026
Miss you too, man! Great seeing you—can’t wait for everyone to see what’s coming. https://t.co/fFRR64p0H5
— Skip Bayless (@RealSkipBayless) September 25, 2026
Sharpe’s post (tagged as a paid partnership) is accompanied by photos of him and Bayless sat at a Polymarket-branded debate desk and a 30-second video that we all could have done without.
In it, Bayless is incredulous at Sharpe’s decision to trade while “the game’s still going on.” Sharpe laughs and says, “Look at this, Skip! What did I tell you? Don’t mess with me, Skip. That’s what three rings gets you: Knowledge!”
Bayless literally wags a finger at Sharpe and says, “Don’t you get me started. You just got lucky on this!”
It’s unclear what the forthcoming commercial will show that’s different from this 30-second clip, but to be fair, it’s also unclear why figures across sports — Bayless, Sharpe, James, way too many more — thought it was a good idea to align with Polymarket in the first place. Is Roger Goodell the only one with restraint?
Polymarket aside, it looks like we’ll be seeing more of Bayless and Sharpe together. Front Office Sports recently reported that Bayless and Sharpe have “filmed a reunion show in the Los Angeles area” intended for Sharpe’s Club Shay Shay podcast.
About Megan Armstrong
Since first getting published as a student by the Kansas City Star in 2013, Megan Armstrong has gone wherever curiosity and stories have taken her, specializing in sports, media, music, and culture coverage. She also has an extensive background in interviewing and profiling public figures. Her work has appeared in Billboard, Boardroom, Bleacher Report, Esquire, GQ, GRAMMY.com, NYLON, Newsweek, Teen Vogue, The Hollywood Reporter, UPROXX, and elsewhere.