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Will Cain is Still Swinging for Fences in America’s Most Divisive Time

Videos by OutKick

This Saturday, Will Cain makes his debut on his new show, Fox & Friends Weekend.

Cain spoke to Outkick on that, his career, his decision to leave ESPN, sports media, life, politics, and much more. 

Bobby Burack: The pandemic has hit the media hard. There were some sports media talents whose contracts expired who had to take less money due to the lack of options on the market. As I’ve reported, I’m told ESPN wanted to keep you. They made you an offer and discussed moving you up in the radio lineup. Why did you choose to take a risk and move in this climate? 

Will Cain: I feel very fortunate that a time when, economically, physically, spiritually, this has been very difficult on most people across America I had an opportunity for a job change. I began talking to Fox sometime in early 2020, I didn’t anticipate moving on from ESPN. I loved the Will Cain Show. We were showing remarkable success and ratings growth. And I loved everybody that I worked with on a day-to-day basis. But over time, as I got to know everyone at Fox, I was very impressed with them as individuals and with Fox as a company.

Fox is one of the few, maybe the only mainstream media outlet that welcomes divergent points of view. And I don’t just mean conservative points of view, Bobby; I mean, welcomes disagreement. 

As I got to know Fox over that time, they talked to me about the role that I would play, and then at the same time, the way the country was changing. I just felt like this was an opportunity at this moment in time. It was important for me to move over to Fox to participate in the national discussion and I’m grateful that I had that opportunity.

Burack: As you mentioned, other media outlets don’t welcome views that don’t fit the narratives spewed by mainstream media. It’s not allowed. I agree, Fox News might be the only one that does. Mostly because every other network runs scared from it.

Is that the No. 1 reason you chose your new home?

Cain: If I had to write two reasons, the number one reason that I moved over to Fox was that I was by both their estimation and mine, opening new doors, not closing any existing doors. I don’t intend to leave the world of sports behind. I’ll continue to comment, contribute to the conversation around sports. I love sports. I’ll be watching my Dallas Cowboys, my Dallas Mavericks, the NFL, and college football — if they play in 2020. 

Fox News offered the opportunity to take part in so many other discussions that, right now, are critical. It’s the future of this country.

Bobby, you know this, for the last five years, I’ve focused almost exclusively on sports. I was happy to leave partisanship behind. I was happy to leave, even to some extent, politics behind. But what I’m coming back to is an environment where principles are being questioned. In fact, principles that I think are dear to this country. Principles to who I am as a person are being rejected. And I have opened the door by moving over to Fox to take part in those conversations.

Burack: Do you look at this opportunity as a way to pave the way for others? On TV, outside of Keith Olbermann, no one has been able to talk both sports and politics at a high level.

Cain: Man, I don’t know if it will open the door for others. I certainly feel grateful and fortunate that I will be able to live in both worlds. It represents who I am. It reflects who I am. I’m somebody that feels very passionate about my sports teams. Even more passionately, I care about this country and these ideas that I think are central to the United States being the greatest country on the history of this planet.

So, I intend to be someone going forward in the media that is capable of participating in both worlds. Will others be able to follow? That’s going to be up to them as individuals and the career paths they’re able to forge for themselves. 

Burack: I want to talk about your show, Fox and Friends Weekend. You tweeted you are friends, not just co-hosts, with Pete Hegseth and Jedediah Bila. How did that relationship begin? 

Additionally, what do you plan to accomplish early on?

Cain: I know both Pete and Jedediah well. Going back to my days working with the Blaze. We did a show nightly called Real News. And it was a table of four to five people, many of whom had disagreements with each other and debated the news of the day with each other. And from the beginning, I really liked both Pete and Jedediah. I liked them as individuals, and we shared many of the same values. Pete and Jedediah are both smart, earnest. They debate with goodwill, and they have fun. Bobby, I gravitate to people who are confident enough to laugh at themselves — and both Pete and Jedediah can do that. 

Fox and Friends is a program that I enjoy watching and I’m excited to join. My first goal will be to fit into a very successful program. I look forward to giving Pete a hard time about the fact that he apparently likes cats. I’m going to debate Jedediah on whether or not that animal that weighs under 20 pounds she calls a dog, is actually a dog. I’m going to have fun with them. But we’re also going to talk about these ideas I’ve referenced several times in this interview with you.

I hope to bring to Fox and Friends a point of view that focuses on the issues and the truth as much as it does politics and partisanship. I just can’t underline and highlight enough that I think those are the issues that Americans care about. It’s the core of who we are. 

I’m excited Fox and Friends is going to allow me to do all of those things. Have fun, talk about sports, talk about politics, but also dive into some of these very important issues.

Burack: What’s the preparation for the show? It will be on very early — 6 am — Saturdays and Sundays. With the pandemic, are you guys even able to meet face to face before the launch?

Cain: I think, and you’re talking to me before day 1 has even started, many of those meetings during the week will take place over phone and conference calls. Fox and Friends is much more of a team sport than a solo radio show is on a day-to-day basis.

Somebody else asked me a similar question, Bobby, about the preparation. I actually don’t see it changing much from my radio show. I put a lot of work, a lot of prep time into doing a three-hour solo radio show every day. And I’m gonna put that same level of effort and work into doing Fox and Friends on Saturday and Sunday mornings.

At its core, my job is to tell the truth. In order to do that, I’m gonna have to read a lot. I’m gonna have to study. I’m gonna have to prepare. But at the core, my job is to tell the truth, and in order to do so, you got to know what you’re talking about. And I’ll prepare the same way I did whether it’s sports or news.

Burack: I want to go back to the industry that you spent the last four or five years in. The one I’ve spent the past three years covering, sports media.

A couple of months ago, I called the industry broken. I got a lot of pushback. Today, I feel even stronger about that. There’s a disconnect between hosts and fans. Only one side is allowed to the party — the left, of course. And the ratings are tanking, as a result. 

Cain: Bobby, man, I totally agree. Let’s diagnose why that is. And if we don’t diagnose it now, we’ll soon be doing an autopsy on why sports media killed its audience totally. An industry that long had a dedicated, enthusiastic, passionate fan base. 

Here’s the ecosystem that led to sports media being completely and utterly one-sided, and, in my estimation, totally out of touch with the audience:

First, the media in general, suffers from a self-selection mechanism. Most people that choose to go into media share somewhat of a similar worldview. On top of that, most major media companies are situated geographically in the Northeast corner of the United States, which also shares that same worldview. So you’re already fishing from a pond of people who, not exclusively, but generally think the same way.

Then you layer on top of those executives that also, by and large, share the same point of view. This has become one of the most self-reinforcing and strongest measure mechanisms in making sports media so one-sided. 

Also, it’s the sports media critics and reporters that will write articles about what shows are great, which talents are intelligent, and who’s contributing valuably to the conversation. But what they’re really writing about is people they already agree with. And that creates a feedback loop because the executives read those articles; they have undue influence. 

Then finally, layer on top of that, social media, which amplifies certain voices. And you have this vortex that makes everyone think that one singular point of view is rational, smart, correct, and reflects the audience. And anybody outside of that point of view they call a contrarian for contrarian’s sake, an attention seeker, or more recently, a racist. That causes them to spin off in extreme directions with their points of view and their topic selection. And their love of sports is totally disconnected from the audience.

Burack: Yes, I blame the decision-makers. Most of the gutless personalities are just trying to get rich. Those who don’t are operating out of fear. Fear is the key. It drives the sports media industry, Will.

Cain: Bobby, I think fear drives more than just the sports media industry. Fear drives corporate America. There’s been a failure of leadership across this country over the last six months at every level, and most people focus on governors, mayors. They focus on politics. What they don’t focus on is corporate America.

Sports media is, simply, just like the rest of corporate America. They are listening to the loudest, smallest, most extreme voices amplified on social media and they’re living in fear of being called a racist. They’re living in fear of falling outside of the quote-unquote, “acceptable points of view.” And along the way, Bobby, they are sacrificing everything. They’re sacrificing their bottom line. They’re sacrificing their fidelity to the shareholder. They’re sacrificing their ratings. In some sad cases, and I know this because I get the private text messages, I get the private calls, they’re sacrificing their own values out of fear of being branded something they are not. 

Fear is driving the day at every level of leadership, but it’s not leadership anymore. It is simply spineless followers at every level of what we would hope would be leadership.

Burack: Roger Ailes once said, and I’m paraphrasing without the exact quote, “I found this niche market in American broadcasting — half the American people.” He was referring to conservatives who weren’t served by the media. You can apply that now, to a larger degree, to Americans just wanting something different. The same, spineless media personalities are the reason Joe Rogan and Dave Portnoy just made a $100 million.

Will, it’s clear, there’s an opening. 

Cain: I used to think that everybody wanted to hear their own opinion, regurgitated back to them in the most entertaining way. I used to think everybody suffered from confirmation bias. I don’t think that’s what’s going on in media today. I think what’s going on in media today is the vast majority of media is coming from one point of view. But now, Bobby, what’s happening is that one point of view has zero-tolerance for disagreement, or openness to any other point of view. 

The vast majority of Americans aren’t looking for a liberal media outlet or a conservative media outlet. They’re looking for an outlet that will tell them the truth, and they’re smart enough to know that in order to arrive at the truth, I’m going to have to hear various points of view. This is where Fox News comes in.

Throughout my career, I have worked at companies where I was the outlier, whether it was CNN or ESPN. I have worked at places where I’ve been surrounded by people who disagree with me. I have enjoyed that debate. To pursue the truth, I think your ideas should be challenged. 

What Fox News represents, to me, is not the last bastion of conservative opinion. Which by the way, Fox has both opinion and a stellar news organization separate from their opinion. What Fox represents, to me, is one of the last bastions of media that welcomes various points of view and disagreements. I think that’s what the audience wants. I think they simply want the truth and they know the process you have to go through to arrive at the truth.

Burack: This fall, do you believe there’s a place for political coverage to dabble in sports more than it has? Because sports coverage sure has dabbled in it. 

Cain:  Well, the last several years, and certainly over the last several months, those two worlds have become almost inextricably intertwined. Whether it’s the coronavirus or Black Lives Matter, sports and politics seem to be somewhat inseparable. 

Like Clay Travis, who you work for, I don’t think you can or should totally divorce politics from sports. It is somewhat impossible. That being said, I think most fans do not tune in to sports to receive someone’s political point of view, but if they are going to, they want to be exposed to both sides. You don’t want to box people out. You don’t want to make someone feel unwelcome. You don’t want to tell your audience you’re evil or racist if you don’t agree with me. 

So what sports media can do, or what political media can do, when approaching sports is just be open to multiple sides of a debate. This takes me back to what I was talking about a moment ago, Bobby, on what the audience wants. The Will Cain Show on ESPN Radio was really about that open forum. It wasn’t “all you who listen to Will Cain must share his point of view.” People who listen knew if you were involved with the show, you were welcome to disagree. You could tell him he was not just wrong, but I allowed people on the air that told me I was immoral, that I was on the wrong side of history. 

I am open to having those conversations. That’s what resonated about the Will Cain Show. That’s why I believe audiences want that exposure. And honestly, that’s what I’m excited about at Fox News. It truly is one of the last places that is open to debate and disagreement.

Burack: Will, in 2017, right before I got to The Big Lead, I interviewed you. A lot has changed since then — for both of us. You told me your life motto was “to sacrifice a single or a double, to hit the home run.” Since then, your career has elevated substantially. Where are you now? What’s your saying?

Cain: Man, Bobby, that’s a good memory. And I’m glad you put me to the maximum I lived by for much of my life. That’s the way I’m built, man. That’s my nature. Maybe that’s the way I was raised. My dad was a small town plaintiff’s lawyer in Sherman, Texas. He lived on contingency fees, which meant if he won, he got paid and if he lost, he got nothing. The home run was pretty much all I ever thought about: “How can I hit a home run?” It’s what motivated me. As I’ve gotten older, Bobby, that’s changed. 

I’m now inspired by guys, quite honestly, like Tom Brady, who have built massive successes based upon hitting the single. That’s showing up every day, that’s discipline, that’s sacrifice, that’s hard work. That is stacking up singles over time. That is what leads to massive success. I think in the investment world, Warren Buffett has lived by that same kind of mindset.

Where am I today in the process? Well, I’ll tell you this: I’m much more focused on singles and doubles than I used to be. I still have a tendency to raise my eyes and look for the fans. But I will tell you, and I know this sounds like pandering nonsense or sentimentality, but while I think Fox News is a good move for my individual career, one of the biggest motivating factors for making this move had nothing to do with singles or doubles or home runs. It had to do with how important this moment in time is for this country. I truly mean that, Bobby. I would do this for less. This is incredibly important to me. 

We’re talking about the foundation of the United States of America. We’re talking about values, like individuality. We’re talking about concepts like the truth. If these concepts are sacrificed at the altar of a huge movement at this given point in time, and I don’t participate in an effort to try to save that culture, to save those principles, I’ll never forgive myself.

Burack: I consider right now, right here today, August 11, one of the most divisive times in our country’s history. You love history and this country. When was the last time America was this divided? 

Cain: When I took this road trip recently, across the United States with my family, one of my go-to questions, when I talked to people whether or not it was in Tennessee or Montana, was: “What is this? “

Anytime I talk to somebody older, “how does this compare to the 1960s? Any other tumultuous times in United States history.” At this point, almost all of them said, this was the most divisive time. This was the most tumultuous time in their lifetimes.

The United States has been through a lot. We fought a civil war. We’ve been through a great depression. The United States has suffered from divisiveness and partisanship, all throughout its history. I believe in the United States. I think it will see its way through. But in my lifetime, this is the most divisive time we’ve lived through. Older generations have told me the same.

And that just means, to me, it’s worth fighting for the United States. We’ve made it through worse. We’ve lived through worse. And we can see our way through this together, but we’re going to have to fight for it.

Burack: A few quick questions before you take off. Who wins the Super Bowl this year?

Cain: I’m just trying to decide whether or not I should be a homer and say the Dallas Cowboys. Man, I really like what the Tampa Bay Buccaneers are doing. I really do. And I know that teams don’t come together from on paper to jelly on the field in that short of time. But I’m a huge believer in Tom Brady. He hasn’t had this kind of talent around him in years and the Buccaneers defense is good. So, I will say the Tampa Bay Buccaneers, 

Burack: Who is the most influential media talent right now?

Cain: Tucker Carlson.

Burack: In five years, will sports media still primarily be consumed through television?  

Cain: Live games will be. As for the shows, I don’t think so.

Burack: One year from now, what will they say about Will Cain?

Cain: Bobby, I don’t know. I don’t care. Hopefully, they’ll be saying I tell the truth.

To interview Bobby Burack, contact him on Twitter @burackbobby_.

Written by Bobby Burack

Bobby Burack covers media, politics, and sports at OutKick.

15 Comments

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  1. Bobby, excellent interview. You showed me a side of Will Cain I knew nothing about. This is the type of in-depth article that makes my investment in Outkick worthwhile.

    I thought the past few years that Will looked out of place on ESPN. I hope he’s successful on Fox & Friends Weekend. I don’t ordinarily watch it, but I will tune in to see Will.

  2. Bobby B. Great interview. I can say without hesitation Will Cain was the only thing ESPN had in their radio line-up that I would consider listening to. Not some right wing thing, just smart and measured. He seemed like an ill fit at the noisy woke grinder filling casing with heaps of bullshit. Saturdays and Sundays I have Euro Golf on one TV and Fox on the other TV as I’m doing paperwork for the week ahead. Pete Hegseth is someone you want in the foxhole with the bullets flying. I know he’s into that whole USA is great and there is so much to be thankful for living in this country – Icky I get it my woke brethren.. I’ll be watching Saturday (traveling Sunday am but you can bet damn sure I’ll record). Slam it Will, you’re in a much better place with a whole lot more eyeballs.

  3. Predicting that this move by Will Cain will be one of the biggest payoffs for a persons’ career. If he just stays himself he will be hitting homers / taters all day. Could be the face of the network at some point. Got talent. For that he stood out at the (kindly putting it) startlingly very average talent at ESPN. Buy stock in this cat.

  4. So many interviews are filled with cliches and scripted answers. Will Cain provides refreshing courageous responses — which is unexpected in today’s world. Also, kudos to Bobby for making it about Will, not Bobby. He gets out of the way to let Will talk. Politics needs Will Cain — it’s great to have him back.

  5. Hey Bobby,
    Excellent interview/conversation with Will Cain. And since you guys go back a ways it was even easier to be real and say what’s really going on in the business you guys have chosen. Thumbs up!!!

  6. Fantastic article Bobby B. Will Cain was a bright spot at the four letter network. Good luck in your new job at Fox News where you can debate issues, unlike ESPN where debate makes you a racist. Articles like this proves that every penny of 99 dollars is well spent

  7. Great article. I really liked him and outside of live sports he was the last person I have heard give an opinion on ESPN. Will is a cool head and it wouldn’t be surprised to see him hosting a primetime show on fox.
    I will be rooting for him..

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