Shannon Sharpe says debating Skip Bayless was more intense than Stephen A. Smith

There might not be anyone more apt to discuss the differences in debating Skip Bayless and Stephen A. Smith than Shannon Sharpe.

The Pro Football Hall of Famer spent seven years as a debate partner with Bayless on FS1’s Undisputed, before the network chose to move on in 2023. And he spent nearly two years as part of Smith’s First Take, before a sexual assault lawsuit, which has since been settled, led to his unceremonious exit from ESPN.

But Sharpe got to see how Bayless and Smith operated up close while learning how to debate, provoke, and engage with both of them. And during Tuesday’s Nightcap, a listener asked Sharpe about the difference between debating with Bayless and Smith.

“When I debated Skip on Undisputed, it was a real debate show. It’s me versus him,” Sharpe said. “I’m literally trying to win. I’m building my case to beat him. And if I can’t beat him, I’m gonna punch holes in his argument and then have his fall flat. Stephen A. is more conversational. I’m not trying to beat Stephen A., I’m not trying to beat them guys.”

Sharpe noted First Take was more of a roundtable format, with each person getting an opportunity to bring something different to the discussion. And since moving on from Bayless on First Take, and later Max Kellerman, to bring in a rotating cast of analysts, Smith has veered away from the traditional one-on-one debate format. Undisputed, however, treated every topic and discussion with more intensity than a debate around LeBron James or the Dallas Cowboys should ever need.

“With Skip, I’m planting my flag right here and I’m not moving off this,” Sharpe continued. “And now you build your case, your argument to support what you say. And that’s what you learn, is that you never bring something into the argument that doesn’t help your case. If you bring it in, it better help your case, because if it doesn’t, all you’ve done is strengthen his argument. My strongest point, I lead out with it. My next strongest, then I go with that. Then I’m gonna flip it over to him, but the thing you gotta do when you’re in a real debate format, is you gotta keep your train of thought all while listening to what he says.”

Sharpe also noted the differences in working for Fox and ESPN. With Undisputed on FS1, Sharpe brought Hennessy, Black & Mild cigars, weed gummies, a GOAT mask, and other things as props that ESPN likely wouldn’t have allowed on the desk at First Take.

“They let me,” Sharpe said of Fox. “And I was like okay, let’s see how far we can push the envelope. It’s just different. Obviously, they weren’t gonna let me bring Cognac, gummies (to ESPN), I had actual weed, actual gummies with THC in them. I’m drinking at 6:30 in the morning! And when I did this, I had no idea it was gonna take off. I’m just having a good time.”

There’s no way of knowing for sure, but if history is any indication, Fox would have been more likely to let Sharpe back on-air after he settled the sexual assault lawsuit against him. ESPN, however, opted to cut ties, despite Stephen A. Smith claiming to want him back on First Take.

Despite Undisputed aiming to replicate the success of First Take when it launched, the shows were different, the networks are different, the debate styles of Skip Bayless and Stephen A. Smith are different. Bayless treats a sports debate as if he’s engaging in literal battle. Smith is more of a performative commenter, who picks his spots and is willing to let his co-hosts be front and center at times. But both were highly successful as sports debate artists in their career, and no one can attest to that better than Sharpe.