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_outlineWill Cain has made a career out of saying what he really thinks, and this conversation was no different.
We talked about faith, family, and the power of conviction in a world that constantly demands you choose a side. Will shared how growing up in Texas shaped his worldview, what he learned from leaving ESPN for Fox News, and why he believes truth and empathy can still coexist in today’s media landscape.
We also discussed marriage, fatherhood, and the importance of raising boys who are strong, kind, and grounded. Will opened up about the pressure that comes with public life, how he handles criticism, and what it means to lead with both humility and courage.
This was real and unfiltered, an honest look at what it means to hold onto your values when the spotlight never turns off.
BTS on Patreon:
http://bit.ly/4nLmOSk
Chapters:
0:00 Intro
4:04 Life as a Cowboy in Montana
12:19 The Sudden Passing of Will Cain’s Father
16:04 Mental Health
18:52 Will Cain’s Upbringing
23:44 Will Cain’s Early Days on TV
28:55 Will Cain Was in the Quinceañera Business?
33:28 Will Cain’s TV Pilot
35:44 First Time on TV
42:11 When Sage Met Will Cain at ESPN
49:18 Skip Bayless Story
51:56 Lessons Learned at ESPN
54:01 Will Cain’s Time at CNN
1:02:03 When ESPN “Turned”
1:11:55 Charlie Kirk
1:14:13 Hope for ESPN?
1:19:03 Second Attempt at a “Lip Pillow”
1:23:20 Fox & Friends
1:26:28 Hawaii
1:33:01 Relationship with Pete Hegseth
1:35:24 Is Fox News Propaganda?
1:38:12 Moving Back to Texas
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