

The search for the next face of the league might be underway, but for ESPN, it has been Stephen A. Smith all along. And it looks like that’s not changing anytime soon. The ever-vocal analyst just inked a whopping $100 million deal, locking him in for the next five years. But before diving into the new chapter, he took a trip down memory lane to reconnect with one of the people who helped shape him into the media powerhouse he is today.
After almost a decade, Stephen A. Smith and Skip Bayless were spotted sharing the screen together on The Skip Bayless Show. Excited about his former colleague’s new achievement, the host asked Stephen A. how he felt about ESPN’s extension. The 57-year-old called it “very humbling” and then, with a deep sense of gratitude, poured out his emotions about the journey. “Very few people on the planet Earth know my story better than you. It was just announced, we’re doing this interview just hours after it was announced I reached the new long-term extension with ESPN, and you got to start back to the origins and where it all began. And it all began with you,” Smith stated.
Then he recalled, “It all began with you and Jamie Horwitz, my former boss over at First Take, pushing for me to be on First Take, being limited to one appearance a week to start off that. And even that, you had battles just to get me on the air, and then ultimately insisting on having me on five days a week. And there’s no way on Earth that that happens without you.” From starting with just one appearance a week, the duo worked hard to get Stephen A. on five days a week. And eventually he has become the star of First Take. So, he made sure to express his gratitude to Bayless and the ex-ESPN executive for pushing him into the spotlight, giving him the opportunity to showcase his talents.
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Stephen A. reflected on his career achievements as a newspaper writer, being in radio, and television personality, including his work on NBA Countdown (formerly NBA Shootaround), but emphasized that none of it would have been possible without the breakthrough of First Take in 2012.
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Oct 23, 2024; Inglewood, California, USA; Stephen A. Smith (Stephen Smith) on the ESPN NBA Countdown live set at Intuit Dome. Mandatory Credit: Kirby Lee-Imagn Images
“To be in the position that I’m in today, to sign the kind of contract that I signed today, it doesn’t happen if it were not for First Take. And First Take never happens if it was not for Skip Bayless and Jamie Horwitz. And so, I’m forever grateful. And I’m forever humbled, because it’s a lot of luck that comes with something like that, to have people to see your talent, to care, and in your case, to trust.” he emotionally added. It even got Bayless emotional. He wasn’t just happy to see Stephen A.’s growth now, but felt the same genuine pride nearly a decade ago when Stephen A. landed his first big contract with ESPN.
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Skip Bayless recalls Stephen A. Smith landing his first major ESPN deal
Stephen A. Smith and Skip Bayless first teamed up as hosts of First Take. But for a brief period, Smith left for Sirius XM Radio. He eventually returned to ESPN with a blockbuster deal and called Bayless to share the news—, even though he believes Stephen A. himself has forgotten.
“You called me. This would have been in 2014… You had come back to ESPN, we had been through, by that point, a couple of years on First Take, and you had gotten your first big new deal with ESPN, and it was a good one for the time,” Bayless shared. Stephen A. confirmed that the year was 2014. It was a multi-year deal paying Smith over $3 million per year.
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Bayless remembered that he was on his way back from meeting his now-wife, Ernestine Sclafani, in Bristol to New York when he received the call. “I was just so happy for you because you had worked so hard to get that deal, and now you’ve worked even harder, and you’ve taken it up and up and up.”
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Bayless further praised Stephen A. Smith for his continued hard work and success in the media industry. With this extension, the hope is that he will continue to show his dedication. It might not sit well with everyone, but his contribution to the field can never be doubted.
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Stephen A. Smith's $100M deal—Is he the true face of sports media, or just overhyped?