Stephen A. Smith and Will Cain on First Take in 2018

During his five years at ESPN, Will Cain became known for his heated debates about social and political issues with Stephen A. Smith on First Take. But he was only told he crossed the line once.

In 2020, Cain left ESPN for Fox News, citing “the direction of the country” as a reason for pushing him to talk more politics and less sports. This week, Smith joined Cain’s podcast. During the interview, they reflected on their time together at ESPN.

Some of their more contentious debates during Cain’s tenure at the Worldwide Leader included the racial aspect of Tony Romo being celebrated by the Dallas Mavericks, Kevin Durant skipping a White House visit while Donald Trump was in office, and Nike signing Colin Kaepernick.

According to Cain, however, as soon as the debate was over, he and Smith would “dap it up” to show they were able to remain cordial even after having a heated on-air disagreement.

“But one time I walked into your office and you said, ‘you went over the line,’” Cain claimed, a recollection that Smith responded to with a puzzled look. “It was Hue Jackson. And you thought I got too angry.”

“Yeah,” Smith said. “But what I’m saying to you is, I wasn’t angry at you. I was saying you got too angry.”

Cain didn’t seem so sure that was Smith’s only gripe from their heated 2018 argument. “Oh,” Cain responded. “I think I said, ‘are we cool?’ And you said, ‘not really.’”

“Now that’s not true,” Smith pushed back. “I would never say that to you because I’ve always appreciated the fact that you stand on what you believe and you’re fair-minded. And I was the one that was encouraging you, when everybody was talking about, ‘Look man, you’re at ESPN and you spew these views’…I was the one who told you ‘Be yourself.’

“And as long as you are you, and you’re fair, we’re good. A lot of times people would say, ‘Man, how do you take that guy?’ It’s a damn debate show! What is he supposed to do, agree with me?”

But on that day back in 2018 when Stephen A. Smith and debated about former Cleveland Browns head coach Hue Jackson, it looked and sounded like they couldn’t stand each other. The argument stemmed from Damien Woody calling out then Browns quarterback Baker Mayfield for being cold to Jackson, who joined the Cincinnati Bengals coaching staff two weeks after being fired by Cleveland.

There were several shouting matches during the 2018 First Take debate about Mayfield and Jackson, with Cain appearing to get set off after Smith questioned his comprehension ability. During his five years at ESPN, Cain was both praised and criticized for bringing “balance” to the network as a conservative voice. Smith welcomed Cain to First Take whenever there was a topic with a social or political tie in, claiming the current Fox News host wasn’t apt to debate him strictly about sports.

“You’re a white dude from the south,” Smith said on The Will Cain Podcast. “I’m from the streets of New York City. Chances are we ain’t gonna agree. But if we respect one another, and we’re fair-minded, and we definitely express our views as accurately as we possibly can, that’s all we owe each other. And that’s cool.”

[The Will Cain Podcast]

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