Will Cain On Shifting Gears and His New Vehicle

Will Cain spent five years at ESPN sticking out like a sore thumb as one of the few openly conservative voices. In April, news emerged that he was departing the network for Fox News, a more natural fit and a place he served as a pundit — along with CNN and The Blaze — before jumping into the mostly sticking-to-sports business.

Saturday morning brings Cain's debut on Fox & Friends Weekend, where he will sit as a co-host alongside Pete Hegseth and Jedediah Bila. He christened his new company phone with a call to The Big Lead to talk about the shifting of gears.

Kyle Koster: So much of the conversation about you is about what you aren't and how you stood out at ESPN. But has anyone ever asked you, directly, who is Will Cain? What does Will Cain believe in?

Will Cain: I think that's driven largely from a misunderstanding of who I am. When people see others who disagree with them, they color by numbers or use shorthand and assign beliefs. They assign personalities and brands and moral characteristics. That's never been more prevalent than it is today. So most of the time when I was talking to people either on-air or off-air I had to go through the process of convincing them of what I am not.

It seems like any time someone disagrees, then the indictment comes down on them and it's their job — an impossibility by the way — to convince you of what they are not. You ask who I am. I am someone who believes in people as individuals. That's who I am. I think I approach everyone both professionally and personally on that level. Am I perfect? No. But honestly, I aspire in every interaction to know who someone is as an individual. What their political beliefs [are] is only one small slice of who they are.

If I look at everyone as an individual then I can judge their ideas, their character, their personality and most importantly to me, their actions. And I try to take people as individual entities and judge those distinct from whatever indictment, trend or brand is going on.

KK: Do you believe that's even possible anymore? For large swaths of people to see each other and not just each other's beliefs? Or does everything get reduced down to the smallest byte or retweet? Can we truly know who people are? I'd argue that it takes too much time, bandwidth, and energy and people have to want to do that in the first place.

WC: It takes effort. It takes investment. It's one of the things I appreciated about having a three-hour radio show every day. I had time to share who I am and what I think with an audience. It takes an investment from the audience to understand someone and appreciate someone who perhaps isn't easily defined.

It's all too easy to reduce people — to read a headline or a tweet about who somebody is and not give a single moment to think about what they think or who they are. I think it's still possible, it just takes real effort and investment.

KK: It's not reading too closely between the lines to see that you've felt misunderstood through the years. What mental toll does that take on someone and how does it effect your energy and drive to even want to be understood?

WC: I told you a little bit about how I approach people. Let me tell you about how I try to live. I try to surround myself with those who are different than me. Those who think differently, those who look differently, those who grew up differently. All throughout my life I made conscious choices to be in those situations. Not as a tourist but as someone who has lived through diversity.

I moved to Montana because I wanted to see the country. I worked on a ranch because I wanted to see a different style of living. I moved to New York and sent my kids to school in Harlem because I wanted them exposed to those who grew up differently, who look differently and in some cases, think differently.

I believe challenges are not only entertaining but they grow you as a person. When I'm sitting around at a backyard barbecue and I'm surrounded by people who think just like me, I'm simply less entertained than when I'm around people who tell me I'm wrong. Who debate me. Who have fun with me. I just want to be put in a state of challenge.

I think religious people should have their faith tested, should ask themselves tough questions. Because the process of being challenged makes you better, makes you stronger. That's who I am. That's what I've sought out.

Now about the toll. It does tax you personally. It's not easy to look at social media and see everyone calling you a racist. It's not preferred to see people suggest that nobody likes you.

But you have to know a couple of things. First, you have to know what the truth is. [The criticism] is nonsense. It's not true. I know my relationship with my coworkers and audience. More importantly, I know who I am. It does take a toll, though, and I'd be lying if I said it doesn't affect you. Especially social media. It's a constant negative feedback loop. But you have to know who you are and not let other people define that for you.

It takes some strength and increasingly it takes some bravery because there are those who will threaten your job for taking something other than the popular line. If you know who you are, you'll sleep fine at night.

KK: How are you going to get that challenge at Fox News? I'm curious how you think you'll keep being pushed by differing viewpoints within the framework of your new show and network. You mentioned on a podcast with Dan Le Batard that Fox is a place where differing viewpoints can come together, which is something I personally have not seen reflected in the programming.

WC: First, on Fox: I think you're wrong. It's one of the few places that welcomes disagreement. If you ever listen to the Joe Rogan podcast or Adam Carolla's podcast they'll talk about their appearances on Fox News. What you hear them say is that they are happy to go onto CNN or MSNBC but don't get invited.

Guys like Adam Carolla are not traditional conservatives. They don't satisfy all your stereotypes of what you think a Fox News personality is or what a viewer is like. They make it very clear which networks like them and are willing to have those conversations.

I know that Fox News is a channel that welcomes people of different viewpoints. It doesn't mean that the host or opinion-maker isn't going to have their own opinions. I think when it comes to welcoming in the challenge, Fox News does it more than any other news organization.

To answer how I'll do it: Throughout my career I have been an extreme outlier from CNN to ESPN. I will be, at Fox, surrounded by more personalities that share my values but that doesn't mean we're going to agree down the line. I've never been that person. If you saw me on First Take or The Will Cain Show, I've never been someone to go along to get along.

If I hear something that I think is wrong, I will not hesitate to say it. To me, that's the ultimate sign of respect. It's not respectful to pretend to agree with everyone else. It's respectful to be honest with your disagreement. Disagreement doesn't have to be disagreeable.

I'll be the same person, looking for challenges and telling the truth on Fox News as I was on ESPN.

KK: I've said this in print and to you privately but I have genuine respect for your interest in seeking the truth whether it comports with your worldview or not. The truth is the truth. I can think of a few instances where you asked questions no one else was asking to give a more complete picture — the OK signs at Wrigley Field and West Point come to mind. What can you tell me as someone who appreciates that? Will you continue to push back and keep that same energy in your new role at Fox & Friends even if that truth may not be what your audience wants to hear or accept?

WC: We used to joke on The Will Cain Show and it became a punchline on Le Batard that Will Cain had a monopoly on the truth. I don't have a monopoly on the truth. What I do have is a complete dedication to the pursuit of the truth. What I mean by that is: I won't always be right. There will be times I get it wrong. I have to be open to the critique and challenge of others, that way we can both arrive at the truth together.

It's absolutely core to who I am. I don't sleep well at night if I make compromises, if I take an exit ramp to be liked or to please an audience. It makes me deeply uncomfortable. I can't imagine, even if I wanted to, I could sit quietly to be liked by any audience if we were sacrificing the pursuit of the truth.

That does not mean you, Kyle, or another viewer who disagrees, will think I'm living up to that standard every time because we'll have our natural disagreements. But anyone who has done the hard work that we talked about earlier in this interview of investing and knowing who I am as an individual will know Will may end up wrong, but I will be trying very, very diligently to pursue the truth.

KK: You've mentioned many times that you got a lot more behind-the-scenes agreement at ESPN than you got publicly. Did you see on-air people taking stances publicly just to play nice? I don't want you to name names but how widespread was that, whether it was born out of not having the courage or the machinations of how sports media deals with dissenting voices? If so, what did it feel like to see that?

WC: I thought [that] on occasion and it disappointed me. I understand why people would make those choices. A vast majority of time the way those decisions are made are through being silent, not saying something you don't actually believe.

Society is attempting to impose a very serious cost to those who fall out of line right now. I think all of us can agree that cancel culture brings public indictments online and now — in the streets — mobs will brand you, indict you, and cancel you if they can for something they believe is not toeing the appropriate line.

One thing that is done specifically is to call someone a racist or homophobic or a bigot of some kind. What that person needs to do is know who they are and what is right. I can't promise you it won't take a toll, it won't come with a cost but it's the right thing to do.

I had a meeting today at my new job and we talked about working through some more difficult times. I said this today and I said it at ESPN: I trust myself on the most sensitive of topics because I know who I am. I know what I think and feel inside. I know what I will say. What I cannot trust is the way people will twist it and turn it.

It takes some strength to realize you're going to stand by your words and let the chips fall where they may on what people do with that. People are doing a lot right now so I can't necessarily blame those who are choosing to stay silent or to toe the appropriate line but I do find myself disappointed.

KK: I think that's natural. I have a hard time understanding the absolute reluctance not to give at least some benefit of the doubt to people. If you can't be fair, at least stop short of thinking the absolute worst of people. And as someone who is in near lockstep with what you're calling the "safe" place to be right now, I do acknowledge some validity in what you're saying about going against it.

More than that, I don't know how I'd live my life if I took it to that extreme. My relationships with close friends and most of my family would be in ruins. So I think it's odd that's how it plays out online. To that end, though, I am curious how you marry the ideas of Twitter not being real life and cancel culture being real. Is it possible you're putting too much stock in what gets tweeted or is that backed up in real-life action?

WC: Both things are true. Twitter is not real life and cancel culture is real. Twitter is not reflective of people in America and what they actually think. Twitter would have you believe that people think the world is descending into absolute chaos and everyone hates each other.

Some of that is true but it's not an accurate reflection of the country I saw as I traveled 7,000 miles and 15 states with my family. Twitter would have you believe that every single grocery store is a fight over who has a mask on right now. But what I saw as I traveled was people making very rational decisions for their own health, their own risk assessment but also being considerate of others' choices. If someone didn't necessarily think a mask was effective they were still considerate of others who saw a mask and were more comfortable.

It does not reflect the vast majority of points of views out there. Twitter would have you believe that most of the African-American population wants to defund or abolish the police when polls show that the majority of African Americans do not want to abolish or defund the police. What Twitter does is constantly elevate extremely loud, small voices.

It is not real life in that way but it does have undue influence and makes cancel culture a very real thing because corporate leaders in and out of the media in every industry right now over-index those the extremely loud small voices. Fear is running rampant. Spinelessness is the status quo in "leadership" across America. People are giving into the fear of being branded as a racist, a bad person, or someone on the wrong side of history. Even if it doesn't reflect real life.

KK: I know you hate to box yourself in and put labels on others, let alone yourself, but what role do you envision yourself playing on Fox & Friends?

WC: I am a person who has an interest in being journalistic. I love asking questions. If you listened to The Will Cain Show, I enjoyed my interviews as much as I did my rants. I'm a naturally curious person. Questions are as challenging as rebuttals. On Fox & Friends, yes, I will be wearing a journalistic hat in asking people questions about their points of view.

You'll also be hearing my point of view and hearing who I am in responding to the news. If you saw me on First Take you know I take what I say seriously but I don't take myself too seriously so I'll be happy to do any of the segments that involve me being goofy and having fun.

KK: Are you nervous?

WC: Yes, I am.

KK: Why?

WC: Because new things come with anxiety. I had rehearsal today and it was awesome. I got to knock a little rust off and remember how to do this. This will eventually become second nature but in the beginning I'll have to feel my way through it. The perfect analogy was said to me this morning. I need to take a few pitches at the plate to see how this pitcher is throwing but I have no doubt that I'll eventually be able to swing for the fences.

KK: Last one here. Everyone knows there is a very famous fan of the show. What will it be like for you knowing that the president is watching?

WC: One of the reasons I was excited to join Fox News was the reach. It's awesome to be at a network that garners millions of viewers throughout the day and among the viewers is the President of the United States. It's humbling.

It will not affect me in terms of what I say, my opinions, or my honesty.