Mediaite Q&A: Will Cain Didn’t Vote For Trump in 2016. Now, He’s the New Co-Host of Fox & Friends Weekend.

Courtesy of Fox News

“Media seems to be obsessed with this idea of everybody marching to the same beat,” says Will Cain — a man who definitely does not march to the same beat. Anybody who has seen Cain go toe-to-toe with Stephen A. Smith on ESPN’s First Take over the past few years knows that Cain thrives off taking the contrarian position.

That’s a trait he’s planning on bringing to Fox & Friends Weekend — where, starting on Saturday, he will serve as co-host alongside Jedediah Bila and Pete Hegseth. Although Cain’s views are much closer to his new colleagues than those of his former cohorts at ESPN, the host does expect that he will run into disagreements with Bila and Hegseth from time-to-time.

And possibly, Cain’s opinions will put him at odds with Fox & Friends‘ most famous fan — President Donald Trump. Cain, who says he did not vote for Trump in 2016, says he is undaunted by the prospect of some Twitter criticism from the president.

“I have a long history of being unpopular with people around,” Cain told Mediaite, in an interview conducted Tuesday. “It hasn’t made me compromise my values and what I think is right to this point.”

Read on for more about what it was like talking politics at ESPN, how Cain’s new show is coming together, and whether he believes Fox & Friends viewers are interested in dissent.

This partial transcript has been edited and condensed for content and clarity. Additional content from this interview will be available later in the week, exclusively for Mediaite+ subscribers.

Mediaite: Congratulations on the gig. It is very different from your last stop, what led you to make the move?

Will Cain: There’s the mechanics, and then there’s the world. The mechanics of my move from ESPN to Fox are that over the last several months, as I began to talk to Fox, I was increasingly impressed with their leadership, their vision for the network, and what they thought of me. They understand who I am, my ideas, my worldview, and they were interested in my point of view.

Then there’s the world. As the last six months or so have unfolded, as much as I love sports, the things that are nearest and dearest to my heart, the values that I try to teach my sons that I live by, the values that founded this country have been not just called into question, but openly rejected. I think as a nation, we’re at a very fragile point in our history, civilizations are difficult to build and easy to tear down.

It just became obvious to me that now was the time to re-enter that debate. Now was the time where if I were to look myself in the mirror at the end of my life and say, ‘Did you let that moment pass? Did you sit quietly as what made this nation great was torn down.’ I wouldn’t forgive myself. As much as I love the Dallas Cowboys, I love the United States of America more. And those two things coming together at this time made me ready to move from ESPN to Fox.

There’s obviously a lot of speculation regarding what ESPN personalities are and are not allowed to speak about. Did you feel you had to make this move in order to say what you want on these subjects?

No. Not once at ESPN was I ever told not to talk about something and I would extend that beyond my radio show to First Take, as well. In neither location did I feel constrained. I did pay attention to what the audience was there to listen to. The audiences were primarily there to talk about sports, and I think most talent — and networks, for that matter — would be well-served to remember that. They’re there for the Dak Prescott, Carson Wentz debate. They’re not there for a one-sided political point of view on the news cycle’s current controversy.

I never felt constrained at ESPN, but I always wanted to keep the audience as a priority. The reason I wanted to move to Fox is to open new doors. I don’t intend to close any. I intend to continue to talk about sports, but open new doors with a broader conversation and a much broader audience. It simply can’t be understated how big and influential the Fox News platform is.

I wanted to get into some of the broadcast formatics of launching in the telecommuting age and what it’s been like trying to develop chemistry with Jedediah Bila and Pete Hegseth as you try and put together a show. Fox & Friends is a long established, high-profile show with a tried and true format, and you are basically trying to jump on board a train that’s already rolling. How has it been trying to work out the kinks from a broadcast standpoint?

So let’s talk about my hurdles and then the show’s hurdles: Will it be difficult in a virtual coronavirus environment to establish rapport and familiarity with Jedediah and Pete? I don’t think so, because I’ve known them for years. I go back with Pete and Jedediah at least seven years or so. We all worked together at the Blaze for some time and did a show called Real News every night. I got to know Pete and Jedediah through that process and have kept up with both to varying degrees in the years since. Pete and I have gotten together on numerous occasions and had a beer in Midtown Manhattan. I think we’re going to be able to walk in, even with the difficulties of not being face-to-face, with some base level of chemistry. We know each other, we trust each other. I think we all respect each other. What that means is we’re going to be able to give each other a hard time. We’re going to be able to tell each other that they’re wrong if we think so and not feel insecure or defensive about that fact. I’m excited about the chemistry walking in to this show that we’ll already have.

Now, there’s my hurdle — to your point. My hurdle is I have been doing a three-hour show long form, 15 minute segments for several years now. I’ve had a lot of elbow room, man. I know that morning television is quicker. There’s three hosts and I will have to edit myself, but life is an editing process. Television is editing. Life is editing. So my job is to synthesize my points, my point of view, and bring them out quicker. That may take a little adjustment period for me, but I’m aware of it going in and that’ll be my own challenge, which I will overcome.

We know about your throw downs with Stephen A. Smith on ESPN First Take. They’ve garnered millions of YouTube views and become the stuff of sports TV legend. Pete and Jedediah clearly come much closer to your worldview than Stephen A., or some of the people that you encountered at ESPN. Do you envision any scenario where there’ll be confrontation? You’ve never shied from debate.

Absolutely. First of all, media seems to be obsessed with this idea of everybody marching to the same beat, you know? I guess do people in the world feel that way? Do they go about their daily lives, because I sure as hell don’t. I wouldn’t be interested in being around a backyard barbecue where everybody shares the exact same lockstep opinions. No, man. I’d be bored out of my mind in no time.

But then on top of that, it’s impossible. I love when people used to listen to The Will Cain Show and they told me, ‘Um, uh, I really love the show. I don’t agree with everything you say.’ To that, I’d say: Who do you agree with on everything? Where does that exist? It’s absurd. Do Pete and Jedediah and I have disagreements despite sharing similar values? Yeah. And I think we’ll discuss them on air. They may not be as combative as my conversations with Stephen A. I doubt they will be, actually.

Here’s the thing that I know about myself. I have almost a religious devotion to this idea that I must adhere to the truth in any situation. I feel bad inside if it’s like, will you compromise there because you wanted the audience to like you, or you want the person across the table to like you, or you want to build an audience. I know I’m sure everybody says that. I don’t sleep well if I ever compromise on that and I will stay that way. When I go to Fox, I will absolutely stay that way. Whether it’s disagreeing with people who’s political parties are supposed to represent my points of view, a particular politician, or co-host, I will always be there with like my religious devotion to what I think is the truth. And it doesn’t mean it has to be big, bad, and ugly — I don’t think it should be. I think the world needs more disagreement. It’s more healthy and it’s more fun.

I would imagine some of those disagreements would come from the show’s biggest fan, the president. I wanted to confirm that you didn’t vote for Trump in 2016. Is that right?

That’s correct.

When a disagreement comes up about the president, how do you plan to approach that? If the president himself is a regular Fox & Friends viewer and occasionally tweets about the show, how do you plan to deal with that?

I have a couple of things to say on that. You asked how I be prepared to deal with it. I will just be honest about my point of view and what I think the truth is. I don’t care if it’s the president or the entirety of the sports media complex telling me I’m wrong and that I should be embarrassed. If I think it’s the truth, I will stand by it. I have a long history of being unpopular with people around. It hasn’t made me compromise my values and what I think is right to this point.

With the president, I have written things in the past and I’ve shared my point of view. I will tell you: time passes and things change. I’ll be sharing my point of view going forward on a lot of different issues. And I will deal with the president one-by-one on each individual issue.

More important than the political race to me right now is the issues and values being debated in this country and that is near and dear to my heart. That is very core to who I am. Is individualism still a core component of not just morality, but success in the United States of America? Or is it a vestige of white supremacy? We can go down the line on core tenets of the American founding and what I think it is to be a good person. And we can talk about all of those that are being questioned and in many cases rejected.

I am here for that conversation. I am here for that debate. I am here for that fight. The president or the Democratic party or the Republican party to the extent that they adhere to those values, I will be open, honest and truthful.

What is somebody who’s just seen the clips of you going to learn — beyond that you’re going to speak your mind and not hold back?

That’s a good question. People used to say to me at ESPN, ‘You’re not who I expect from watching First Take,’ meaning when they ever listen to the radio show, watch the radio simulcast on ESPN, when I just saw you on First Take. I think that’s because depending on the environment you’re in, often, only certain elements of your personality come out. And First Take is a very combative environment, right? We all liked each other on First Take. At the end of that combat, we would dap each other up and have a good day. But it was a very combative environment where it was built upon strong opinions being debated.

What people will learn about me and I think what many on the radio audience learned about me, isn’t why I have these strong convictions. I’m not only open, but I am openly interested in hearing points of view that are different from mine. I’m open to hearing how I could be wrong. I will be real and authentic and true to who I am through that entire conversation to that entire debate. But I am not someone who wants to block anybody out, not just just because I want to build the biggest audience possible, but again, because I just think that’s what people want. I know it’s what I want. I want it. I think what people will learn about me as time goes on is I’m open to their points of view, and who knows where the disagreement will come from.

Do you feel that Fox & Friends viewers share that sentiment with you? Do you agree they’re looking for that?

I think Fox News viewers in general are open to hearing the other side. I think Fox News is one of the really last media institutions that brings anybody on of divergent viewpoints. Yeah. I think that they are interested in hearing it.

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