Will Cain thought Black people loved him when he was at ESPN. ESPN management, however, didn’t appear to agree.
Cain joined a recent episode of The Sage Steele Show where they discussed having conservative viewpoints while working at ESPN. Throughout much of his ESPN tenure, Cain was embraced by First Take for bringing a conservative viewpoint to the show. And while he often sparred with Stephen A. Smith and Max Kellerman over issues such as Colin Kaepernick taking a knee, Cain believed he was still relating to the show’s Black viewers.
“I said to Stephen A., I said on camera, in a lot of ways, Black guys and I — people don’t believe this — we hit it off because the way we grew up and the culture we had is similar,” the North Texas native told Steele. “I’m painting with a broad brush, not everybody does. But the debate world, the idea that I can say something to you in disagreement and it’s not mean, and it doesn’t mean I don’t like you, especially around the world of sports, I just never felt like that was a thing. So what if I said you’re wrong…and a lot of the Black guys at ESPN were operating on the same wavelength.”
ESPN management, however, didn’t appear to be sold on Cain’s assessment that he was hitting it off Black people during his time on First Take.
“One time management told me this,” Cain recalled. “They said, ‘We did a focus group, Black people hate you.’ And I said, ‘No, they don’t, I meet them all the time, they love me.’”
According to Cain, the unnamed ESPN exec countered by saying, “Black people are polite, they’re not going to tell you to your face.”
Steele asked if the unnamed ESPN executive in this story was EVP Dave Roberts, to which Cain laughed and nodded his head while repeating, “it was management.” His reaction seemingly confirmed it was Roberts, who is Black, without actually naming the executive.
Cain ultimately left ESPN for Fox News in 2020 and now hosts a daily late afternoon show on the cable news network, but we’d have to run a focus group to know whether he took First Take’s Black audience with him. Cain’s profile, however, undoubtedly reached new heights during his time on First Take, where he leaned right of where Max Kellerman and even Stephen A. Smith was leaning at that time.
Joining ESPN in 2015, Cain was one of the few openly conservative voices on a network that is often accused of leaning left. Times have certainly changed in the years since, with Donald Trump joining The Pat McAfee Show on ESPN on Tuesday afternoon.

About Brandon Contes
Brandon Contes is a staff writer for Awful Announcing and The Comeback. He previously helped carve the sports vertical for Mediaite and spent more than three years with Barrett Sports Media. Send tips/comments/complaints to bcontes@thecomeback.com
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