Can Skip Bayless Revive His Career Doing New Show With Gilbert Arenas?

Despite what you may read online, Skip Bayless is one of the most influential sports television personalities of the past 20 years.

Bayless’ unlikely success is the reason debate is a fixture of sports-talk television today. Stephen A. Smith would not be the industry’s biggest star had Bayless not handpicked him as a co-host in 2012. Likewise, Shannon Sharpe’s career resurgence began when Bayless tapped him as his debate partner after moving to FS1 in 2016.

Remarkably, Bayless reached stardom without ever appearing on a mainstream sports network like ESPN’s flagship channel or NBC. Instead, he built his career on smaller platforms such as ESPN2 and FS1.

That said, his influence has waned in recent years. After Sharpe left FS1 in 2023, the Bayless-led Undisputed lost more than half its audience, at times averaging as few as 30,000 viewers per episode.

In 2024, Bayless left network television and launched a YouTube channel featuring a solo podcast and a weekly series with his wife, Ernestine. But the channel has yet to gain traction. Recent episodes of The Skip Bayless Show and Skip vs. Ernestine drew just 26,000 and 1,200 views, respectively.

Still, Bayless may not be entirely responsible for his recent struggles. After Sharpe’s exit, then-FS1 executive Charlie Dixon retooled Undisputed into a clunky format. Bayless was shifted into a moderator role and paired with former athletes like Keyshawn Johnson and Richard Sherman, who showed little interest in debating someone who had never played professionally. And though Bayless’ move into independent media has been disappointing, digital success is often driven more by marketing and algorithms than the personality behind the channel. 

Thus, Bayless hopes to revive his career with his latest venture.

On Tuesday, he debuted a new debate program in partnership with former NBA star Gilbert Arenas. The Arena: Gridiron features Bayless, Arenas, Aqib Talib, and Gerald McCoy, streaming live on Arenas’ YouTube channel.

We've been critical of Arenas as a person. The former guard appears to have a real issue with white basketball players and was recently arrested in connection with an illegal gambling business run out of his California home. However, his channel boasts more than 1 million subscribers, and most clips draw well over 100,000 views. Bayless needed a platform with a built-in audience, and Arenas provides it. In turn, Bayless should help expand Arenas’ brand beyond NBA circles. On the surface, the partnership makes sense for both.

Early teasers suggest the show will be looser and less polished than Bayless’ previous debate programs—and he’d be wise to embrace that format.

Bayless originally made his name on television defending Tim Tebow, sparring over LeBron vs. Jordan, and championing Tom Brady. But Tebow and Brady are retired, and LeBron is well past the legacy-building stage of his career. Put simply, Bayless has needed to evolve for quite some time.

LOS ANGELES - (L-R) Skip Bayless, Lil Wayne and Ernestine Sclafani attend Lil Wayne's 40th Birthday at The Nice Guy on September 25, 2022. (Photo by Jerritt Clark/Getty Images for The Goldwing Group )

Fortunately, he may be more versatile than he realizes. After recent appearances on Pardon My Take and in an interview with Sage Steele, multiple media personalities told OutKick they were surprised by how much more likable Bayless appeared. When not performing, he comes across as relaxed, funny, and even introspective.

Note: Bayless had originally agreed to an interview with OutKick, but backed out last month.

He also has a rare ability to connect with people across various cultural and ideological lines—whether it’s Steele, Arenas, Lil Wayne, or Nelly. Admittedly, Bayless’ chemistry with younger black rappers feels far less forced than one might expect from a 73-year-old white man.

In short, we aren’t writing Skip Bayless off yet. As much as bloggers and the self-styled cool kids of sports media would like to declare his career over, this latest venture might be exactly what he needs to reestablish himself.