The Other Side of Skip Bayless | Sage Steele Show | EP 68
Release Date: 08/19/2025
The Sage Steele Show
Jason Whitlock showed up ready to talk about everything, and he did not hold back. We talked about his long and complicated history with Stephen A. Smith, why that friendship changed, and what he believes Stephen has gotten wrong through the years. Jason opened up about the choices he has made in his personal life, including why he never married or had children, and how those decisions shaped the man he is today. And because this is Jason Whitlock, there was plenty of laughter too. I pressed him on his top ten eye candy list, and he broke it all down with the honesty and humor only he can...
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I sat down with Dave Ramsey at his headquarters in Nashville for one of the most personal and inspiring conversations I’ve had on this show. Dave opened up about losing everything in his 20s, filing for bankruptcy as a young husband and father, and how that painful chapter became the foundation for the empire he built today. We talked about what it means to be a real leader, how faith guided him through failure, and the difference between being a boss and being a servant leader. He shared what those years taught him about marriage, fatherhood, and humility, and how his faith continues to...
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Bear Handlon has lived a life of service, from the battlefield to the boardroom. The former U.S. Navy SEAL and CEO of Born Primitive joined me for a conversation about purpose, leadership, and what it means to truly give back.
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Will Cain has made a career out of saying what he really thinks, and this conversation was no different.
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Riley Gaines has become one of the most recognizable voices in the fight to protect women’s sports, but in this conversation, we got to see another side of her as a wife, a new mom, and a woman learning to balance purpose with peace.
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Arynne Wexler made a name for herself online as “Non Lib Take,” but who she’s becoming now is far more interesting than who she was.
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Allie Beth Stuckey has never been afraid to speak truth in a world that often rewards silence. In this conversation, we talked about faith, conviction, and what it means to stand firm when culture pushes you to conform.
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James O’Keefe has never been afraid to ruffle feathers. From founding Project Veritas to launching OMG, the O’Keefe Media Group, his investigations have taken on some of the most powerful institutions in America.
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From building WWE with her husband Vince to running for the U.S. Senate in Connecticut and later serving in President Trump’s cabinet, Linda McMahon’s story is nothing short of remarkable.
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You probably know Justin Danger Nunley from TikTok, where millions of people wait for his signature line: “Listen… did you know?” But behind the viral videos is a story most people have never heard.
info_outlineSkip Bayless has built a career on delivering sharp takes, holding bold opinions, and never backing down from a debate, but this conversation revealed a side of him that most people never see.
We discussed the work ethic that has fueled his decades in sports media, from his early days as a newspaper columnist to becoming one of the most recognizable personalities on television. Skip opened up about the sacrifices, the criticism, and the pressure that comes with living your life in front of an audience every single day.
He shared personal stories about his childhood, the moments that shaped him, and the relationships that have kept him grounded in a business that can easily pull you away from what matters most. We also got into his views on competition, how he prepares for those high-stakes TV debates, and why he’s still as passionate about sports as he was on day one.
This was Skip Bayless beyond the hot takes- a thoughtful, driven man who’s as committed to his craft as he is to staying true to himself.
The Sage Steele Show is a weekly podcast hosted by former ESPN anchor Sage Steele. Each week, Sage sits down with entertainers, athletes, business people, and politicians to have deep dive personal one on one discussions that enlighten, entertain, and engage. There’s a whole big world out there that’s not just sports, and Sage wants to talk about all of it.
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