On the outside it looks like Stephen A Smith has always had the perfect life. He is the face of a hit show, someone the network values enough to shell $100 million dollars on. But the journey to the top was no easy feat. One such instance came in 2009 when ESPN fired him, ironically due to a contract dispute. But just when it felt like Smith’s media career had seen its end, there was one man who chose to believe: Skip Bayless. Bringing Smith back as a guest debater wasn’t just friendship, but a selfless move only possible by a “brother from another mother”, words Smith often likes to thank his former co-worker with. But enough about thanking because it looks like the First Take host might have got the chance to actually repay the kindness 17 years later.

Front Office Sports’ Michael McCarthy reports that Bayless is scheduled to appear on First Take this Friday, May 8, alongside Smith. ESPN confirmed the appearance, describing it as a “one-time show.” This will be the first time Bayless and Smith have appeared together on First Take since June 2016—the month Bayless left ESPN abruptly to co-host Undisputed alongside NFL legend Shannon Sharpe at FS1. As for Bayless, he seems more than excited and ready for this reunion.

“CAN’T WAIT FOR FRIDAY” on social media. But for the longest time, the idea of a reunion was completely off the table. So, what changed?

When Fox Sports began negotiating a buyout of Skip Bayless’ $8 million per year FS1 contract in 2024, ESPN killed the reunion talk. The network said they were sorted with the First Take cast, and Smith himself said, “Skip Bayless and Stephen A. Smith, together… are over. It sounded final. But less than two years later, ESPN reversed course. So is this just brotherhood? Well, that’s questionable.

The timing isn’t random. While most of ESPN’s studio shows are enjoying good growth, First Take has been a little bit of an outlier. Get Up is up 18%; The Pat McAfee Show is up 16%, but First Take has only climbed 5%. Sure, it’s good growth, but there’s a gap that is noticeable. And this is where Stephen A. Smith comes in.

Smith is not just a host anymore; he is the executive producer of the show. Over the years he has made many calls behind the scenes. Whether it was time to move on from Max Kellerman in 2021 when he felt the show had stalled or playing a major part in bringing Shannon Sharpe into the mix as a recurring voice during football season. He has made calls he thought would work, and he has had the freedom to make the call.

So sure, ESPN can call this a “one-time reunion,” and it’s okay to take this with a grain of salt. But if Friday delivers, and if the energy comes out in numbers, then Smith may push for more. And this change of dynamics between the two didn’t happen overnight, so it is not really surprising that they would want to reconcile too. It all started over a podcast.

In March 2025, Smith taped an episode of The Skip Bayless Show, their first time on air together since 2016. By November, the two were photographed together at Nate ‘n’ Al’s deli in Beverly Hills, seated in a booth with Bayless’ wife, Ernestine. The image caught enough people off guard that the person who shared it actually felt the need to clarify that it wasn’t AI-generated. But that’s not all.

Then came Super Bowl LX Radio Row in February 2026, where Smith and Bayless shared a camera on The Arena: Gridiron—their first in-person, on-air appearance since the split. At the time, Bayless had noted how he and Smith had impacted the media landscape.

“I would say that no one has ever quite matched the chemistry that maybe God about gave us. It’s hard to find; you can’t teach it or coach it. It just worked.”

Stephen A. Smith had agreed at the time, taking a shot at the critics instead. “You’re right,” Smith said. “And I think it’s a lot of BS when it comes to that stuff because you’ve got a lot of jealousy, a lot of envy, because people look at what we’ve been able to achieve and they’re like, ‘Why them?’ Why not us?”

And truly if you see how Bayless has done in the second act of his career, you would say the same, “why not him?”

How Skip Bayless built his second act

Now the road was not easy for Bayless, and after leaving ESPN in 2016 to co-host Undisputed alongside Shannon Sharpe. Things should have been great, two big personalities in one show. However, the relationship cracked and in an extremely public way. 

There was one incident when Bayless took a personal jab saying Tom Brady was “better at 45 than you were at 35.” After that comment, came the aftermath of Bayless’s controversial tweet during the Damar Hamlin on-field collapse, which again drew some serious backlash and strained the already rocky relationship. Things never worked out, and by 2023, Sharpe agreed to a buyout and left the show. His leaving left a gap in the show and it never found its footing back. 

By 2024, Fox Sports negotiated a buyout of his $8 million-per-year contract, and Undisputed was ultimately canceled. Bayless didn’t give up, and he simply pivoted.

At 74, he still commands attention, but in a way very few sports media personalities can. Today he has built The Skip Bayless Show on YouTube, which has over 250,000 subscribers, while his social media following is nearing four million. He’s also got his feet into newer digital spaces, recently collaborating with Gilbert Arenas on The Arena. In other words, Bayless found a new lane that still keeps him very much a part of the conversation. And this matters.

ESPN is calling May 8 a “one-time show.” But the network that flatly refused to have Skip Bayless back is now the one hosting his return. And Smith, who once declared their TV Partnership “over” on his own show, will now be sitting across from him once again. Whatever ESPN says about a single appearance, the positioning has clearly shifted. The question is, will this be enough to create a permanent reunion?