‘You Can’t Expect to Win 100 to 0’: Will Cain On Why He Loves Debating Democrats on Hit Fox News Show

The advent of President Donald Trump’s second term in office marked the launch of a new show on Fox News: Will Cain, the former CNN contributor and ESPN analyst, who took over the 4 p.m. hour of the network for a new kind of program. 100 days in, the Dallas-based show has proven to be a success, with strong ratings and buzz around its programming.

Cain, who replaced Fox News veteran Neil Cavuto, has brought to the show more pro-Trump opinion than his predecessor, who distinguished himself on the network with straightforward anchoring that often drew the ire of the president.

Upon taking the vacant slot, Fox News CEO Suzanne Scott and President Jay Wallace directed Cain to do something different in his new show. Cain took that direction to heart in more ways than one.

Cain hosts the program as a brash talker with strong opinions. Unlike the rest of the cable news industry, he eschews lapel mics in favor of a stand-up mic that gives the show a talk-radio feel. And perhaps most importantly, whereas most cable news shows are based in New York or Washington D.C., Cain hosts from a studio based in Dallas.

I called up Cain at his studio in Dallas to discuss his rise in TV news that took him from CNN contributor, to ESPN analyst, to co-host of the Fox & Friends Weekend show, and finally to hosting his own program, The Will Cain Show.  

Perhaps the defining characteristic of his new show, or the one aspect that Mediaite delights in covering, is his willingness to bring on Democratic politicians to engage in debates on the hot-button topics of the day.

In today’s hyper-polarized media climate, where podcasts are a swamp of like-minded individuals, having ideological diversity on any program is refreshing.

Yes, Fox News has Jessica Tarlov, who co-hosts The Five, among other liberal contributors, and CNN has Scott Jennings and a few others to hold down the MAGA fort. MSNBC’s only Republicans are so “Never Trump” that they are often indistinguishable from others on the network. So I asked Cain about his decision to invite some heavy hitters in the Democratic caucus on his new show.

To my surprise, he asked what I thought about it. “My question to you is, and I ask this in genuine curiosity, What do you see from us that we are doing differently and inviting these figures on at The Will Cain Show?”

“Well, I’ve long thought that the world really needs more of this dialogue,” I said. “And so what I see is I see a respectful, thoughtful conversation.”

I went on to explain why, despite the liberal condemnation of California Governor Gavin Newsom’s decision to engage with Charlie Kirk and Steve Bannon, there is a part of me that appreciates the dialog and think it’s good for a divided nation, even if Kirk and Bannon are pernicious bad actors in the information wars.

“First of all, very simply, I like it. I like the interaction,” Cain said. “I liked the back and forth, and I think my career evidence is that. I was a contrarian voice on CNN, where I had a ton of back-and-forth with people like Soledad O’Brien or Eliot Spitzer. I moved to ESPN and I have basically a job in debate for a while on First Take with Stephen A Smith and Max Kellerman. I think it’s fun. But you have to be careful because fun is not good enough for the audience. Our job is not to provide heat, but it is to provide light.”

“So what does debate actually do?” he continued. There are people who are much smarter than I who talk about this thing called the Hegelian dialect, that there are two diametrically opposed sides and there has to be a winner and a loser in a zero-sum game. And I try not to fall into that trap, I really do. Because I think there’s so much to learn from people that I disagree with. And it may be that I learn that I was right. But there is something to learn in these exchanges and my endorphins fire and I have fun.”

“And so whether or not it’s Congressman Maxwell Frost or Jake Auchincloss or Jason Crow or Dan Goldman, they have, if not extended the first goodwill, perhaps I did by the invitation, they’ve accepted the goodwill. And I intend to continue the goodwill in that conversation,” he said.

“Back to my currency being authenticity, I think the first thing you have to do, and I think you and I together, and I’ve been open about this stuff, about the failure of other media organizations, has started their relationship with the audience on a false note,” Cain continued. “Do not pretend objectivity when you don’t have objectivity. Own your bias.”

“Obviously, I have a point of view, Colby,” he said. “And I think the audience should be and is aware of my point of view. But that shouldn’t be a point of view that lives in a glasshouse. And I should be able to subject my point-of-view to those that disagree and see if it stands up or if theirs stands up. And so I come into these debates with everyone understanding Will has a certain point of view and we should know that going in. I’m not gonna feign objectivity, right? So there will be a level of debate to it where I think I’m right, they think they’re right.”

“And so they think that’s the next big step in our move towards the Handmaid’s Tale autocracy,” Cain snarked about progressive hyperbole. “But you know what? He knew that moment that day, and I didn’t. And so I have to own that in that moment, and that’s what happens.”

“My job’s not always to be right, my job is to be real, and you can’t expect to win 100 to 0 in a debate.”

The Will Cain Show airs every weekday at 4 PM on Fox News.

Watch above via YouTube/Mediaite.

This is an opinion piece. The views expressed in this article are those of just the author.