When conservatives rip ESPN for allegedly being too "liberal," the network likes to counter, "What about Will Cain?"
The self-described political conservative/libertarian has had a rapid rise since joining ESPN less than three years ago. His national "Will Cain Show" debuted Jan. 2 on ESPN Radio and ESPNEWS (3-6 p.m. ET). He provides a valuable balance to ESPN and has become a virtual third debate partner with Stephen A. Smith, Max Kellerman and Molly Qerim on "First Take," which just posted its most-watched February.
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The native Texan has a unique background for sports media. He is a licensed attorney and politico who previously served as a political analyst for CNN and Glenn Beck's The Blaze as well as a contributor to National Review. He's no social justice warrior. But can you name another ESPN talent who has appeared on everything from ABC's "The View" and HBO's "Real Time" with Bill Maher to MSNBC's "Morning Joe" and Fox News?
Cain's not afraid to mix it up with anybody. When he complained about people being offended by the Washington Redskins and Notre Dame Fighting Irish nicknames on "The View," Whoopi Goldberg countered: "Spoken like a true white guy." When NBA star Patrick Beverley tweeted Cain "knows nothing about basketball," Cain jousted with him on Twitter and on his show.
During a troubled NFL season when even "Monday Night Football" announcers Jon Gruden and Sean McDonough seemed horrified at the violence perpetrated on the field, the lifelong Cowboys fan was a full-throated defender of football.
Cain ripped attempts by states such as California and Illinois to ban youth tackle football. The war on football is part of the culture wars, he said: "Football has come to represent toxic masculinity."
Cain has hard words for the media, too. The press claims to love diversity and speech, but there's too little diversity of thought, according to Cain. They hate having their own views challenged. Too many sports journalists, he warns, are looking for an excuse to share their own personal views on politics when they should stick to what they know best.
Cain lives in Manhattan's fancy Upper West Side, yet considers himself something of a Texas gunslinger. His Twitter avatar is Robert Duvall's Gus McCrae from "Lonesome Dove." He quotes Val Kilmer/Doc Holliday's memorable challenge from the "Tombstone" movie Western: "I'm your Huckleberry."
Sporting News' Michael McCarthy interviewed Cain about his growing footprint at ESPN. Excerpts:
SPORTING NEWS: So how will the "Will Cain Show" stand out from all the competition?
WILL CAIN: It will stand out because of who I am, my unique point of view, that I think stands out in itself in the sports world. More than my perspective is unique, I want the "Will Cain Show" to be a place where nothing goes unchecked, nothing goes unchallenged. Too much of our media, and not just sports media, but media in general, is one where the people with the voices live in glass houses. They feel like their opinions are either above challenge or that they’re incapable of withstanding challenge. Look, when I’m going back and forth with somebody, that’s when I feel the most alive.
From the days when I was a kid, and I would sit at the dinner table with Dad, we would debate everything, from the best hamburger in the world to the most important news items. We always had real challenging conversations. That translated to hanging out with my buddies. It wasn’t always something cerebral or important. It was "Why are you dressed a certain way?" (or) "Why did you do your hair a certain way?" Every time it became challenging, most of the times in a fun way, that’s when it became real. I want the "Will Cain Show" to be real. I want callers, guests and my producers to feel emboldened at any moment to challenge me on anything I say.
@stephenasmith I’m convinced that @willcain knows nothing about basketball!!! Nothing!!!! Just reading stats!!!
— Patrick Beverley (@patbev21) February 14, 2018
I’m convinced you’re a good player Pat, so I guess I should revisit that.
— Will Cain (@willcain) February 14, 2018
In the meantime, I won’t be extrapolating two games into infinity. https://t.co/hd7HWWoEZ3
SN: How did you quickly become a regular on "First Take"?
WC: The format and the idea aren't foreign to me. In some ways, I feel like I've been preparing for "First Take" my entire life, from my childhood to my professional career. When I was in politics, I debated a Nobel Prize-winning economist, climate change activists, governors, senators, congressmen. I debated anybody on an issue I felt strongly about. There was no resume that I was afraid to go against — or an experience that negated my point of view. So the first time I sat down on "First Take" with Stephen A., I felt immediately at home, not just with the format but with Stephen A. himself. We hit it off. We had chemistry. We had the ability to debate vigorously — and take none of it personally.
Then when Max and I started appearing together as well, I can honestly say I felt the same way with Max. He enjoys the back-and-forth, enjoys the challenge. Max and I have very different world views. There's been a handful of occasions where we've had really, really heated debates. I've texted them afterwards to say, "Hey, just want to let you know, none of that was personal." Max has always said, "It never is, you don’t even have to clarify." That’s what we do and that's how it is.
SN: You break Stephen A.'s chops on the air, but he still laughs, like you telling him you can drive on him for layups anytime you want. How do you get away with it?
WC: Look, that’s how it was with me and my buddies. I've had these conversations with him and about him. Stephen A. and I are opposites on every surface level you can imagine. Look, I'm a rural white guy from a small town in Texas. He's a black guy from Queens, N.Y. On the surface you'd think "polar opposites," but that’s not necessarily true. The way we interact with people, the way we think you should engage with each other, that's how it was with my friends, man. Busting each other's balls. That’s the way it is. From the beginning, I've been emboldened to do that with Stephen A. He doesn’t take it personally. It makes it more fun. It was never a stretch, to be honest. That was it. Honestly, it always felt natural.
SN: So where in the world are Stephen A. and Max? Looks like they work from the road a lot while you and Molly mind the store in Bristol.
WC: Hell, I don't know. Stephen A. is the nomad of TV. He could be anywhere from Philadelphia to Los Angeles, to wherever the NBA game he’s watching that night. I think Max is often in LA. But you have to ask them. I honestly don’t know most of the time.
SN: You live in New York City. Will you be working out of ESPN’s new South Street Seaport studio when it finally opens?
WC: A lot of that is to be determined. Obviously, I think there are some conversations about when or if "First Take" will move down there. If that’s the case, I’m sure I will be down there for "First Take" from time to time. I already do the "Will Cain Show" twice a week from New York. I do it from the ESPN New York radio offices. We're discussing whether or not the "Will Cain Show" will go down to South Street as well, or stay up [in Bristol].
SN: When ESPN is accused of being a politically correct sports version of MSNBC, they say, "What about Will Cain? If we're such flaming liberals, why is he getting more air time?" So, Will, how do you feel about carrying the complaints of conservative ESPN haters on your shoulders?
WC: I don’t think that I do. I never think about that. Last week, we had a conversation [on "First Take"] . . . I was asked how should white America feel about whatever we were discussing. I said, "I don’t speak for white America. I speak for me." These kinds of things: He's a conservative male. Yes, these are parts of what I am, but they’re not who I am. Any of them, on their own, are not the first things I'd use to describe myself, so I don't feel any burden, or feel any pressure, to carry the point of view for conservative America. What I do is I give my point of view. Every situation I walk into it is, "What do I think as an individual about these things?" I'm not trying to get on a soapbox. But all too often when it comes to issues, and also how we judge each other, we do it on these group identifications. Who is he?
But I'll promise you this: My point of view on most issues, my point of view on political issues, doesn’t check all the boxes for any movement or any ideology, so I don't feel any burden to give voice to anybody but myself. If there are people out there who identify with it, that's great. That will be awesome. If there are people who disagree with it, and who want to engage with it, that’s even better.
SN: As we saw at the recent CPAC (Conservative Political Action Conference) conference, even they can't agree on what a true “conservative” is any more, right?
WC: That’s absolutely true. It hasn't been more in flux since the 1950s when William F. Buckley launched National Review.
SN: Has ESPN has become too liberal?
WC: I would say that I do think my point of view is unique at ESPN. Look, that’s not a problem for me as an individual. I like being around people that I disagree with. If you look at my career path, I spent time at Fox News, I was at CNN. That wasn't just because they offered me a job. It was because that’s where I wanted to be. I always wanted to engage with people who disagreed with me as opposed to high-fiving the people who agree with me. I am unique at ESPN. Most people’s point of view is different than mine. I think a lot of that comes across.
SN: When Laura Ingraham of Fox News said LeBron James should "shut up and dribble,” ESPN strongly backed LeBron’s right to free speech. Some thought Ingraham was dog-whistling for racist whites who hate millionaire black athletes. But you said LeBron should not be "inoculated" from criticism, that if LeBron wants to enter the political arena, then he should be ready to give and take punches like everybody else.
WC: Absolutely. I believe two things about that story. First, there was the question of whether what Ingraham said was racist. I am reluctant to immediately read into people's motivation and character, then extrapolate. So what motivated Laura Ingraham? Was it racism that motivated her point of view? Well, looking back over her career, I find many examples of her making similar statements toward anchors and singers and so forth, so there’s evidence she plays this "Stay in Your Lane" game consistently.
What I'm unwilling to do, and I'd like to think I'm very consistent on this, is to read into someone’s intention and character, so when I go on "First Take," or on the "Will Cain Show," to talk about LeBron and Laura Ingraham, the first thing I want to say is we can't just go about castigating everybody we disagree with. We can't make them immoral. We can say they're wrong. Sometimes just being wrong is a heavy enough hammer, right?
[Spurs coach] Gregg Popovich was right about many things he said about LeBron. LeBron’s story is absolutely inspiring and uplifting. LeBron is an absolutely amazing basketball player, among the greatest of all times. But none of them inoculate him from criticism if he ventures into these areas. I think it's condescending to say, "Well, he’s above criticism," or, "We shouldn't question LeBron James." No, it's respectful to engage and say, "This is why he's wrong and this is what he's wrong about."
SN: Given Fox News caters to conservative viewers, wasn't it a natural for them to target ESPN and LeBron?
WC: It doesn’t surprise me that it was Fox News. Again, LeBron ventured into their world with that commentary. Secondarily, he's one of the biggest stars on the planet. Those two things, if you’re in a TV meeting room, you’re like, that’s a definite go as far as discussing. As for the perception about ESPN within conservative media circles, what I would say is: Listen to Will Cain. Come enjoy the "Will Cain Show." You won't agree with everything I have to say, I make no promises with you on that, but maybe you'll hear some diversity of opinion.
SN: You hear it all the time: Why can’t ESPN "stick to sports"? What about it, Will?
WC: I'm sympathetic to that completely. Even though I come from a political background, I would say my show is one of the most reluctant to go into political spheres on any sports network, not just ESPN. I know why the audience is here. I know why they come for sports, what they want to listen to. They don’t go to the toy aisle to buy Metamucil but to buy something they want to have fun with. That's what we are. That's what we do. At times it’s going to be unavoidable. Those two worlds are going to collide. The difference is, do you go looking for it? Do you look for excuses? If every time sports just slightly touches into the world of politics, or politics slightly touches into the world of sports, is it an excuse for you, a green light, to go down the path of having the political conversation that’s pent-up inside you?
I can't take that away from some of my colleagues. Some of them feel very passionately about these issues. They feel a burden, and a responsibility, to give voice to things that they feel are underrepresented. For me, I want to balance those things against why I know the audience is here. Maybe, Mike, I got some of that out of my system by spending five years in politics. I knew when I came over here what I signed up for. I tried to be respectful of that.
SN: Has it become impossible to "stick to sports"? After all, if Steve Kerr or Popovich, not to mention LeBron or Kevin Durant, weigh in on Trump, don't you have to cover it? Is ESPN supposed to ignore it?
WC: No, we can’t. It's impossible, as you point out, to be completely free of it. It just goes back to: Is it worthy of our time, our attention, our voice? Or are we looking for excuses to talk about things that we know are not part of our job description?
SN: To that end, did Jemele Hill go too far calling Trump a white supremacist?
WC: Yes, I think Jemele did go too far. I really like Jemele. We have interactions here at the office. I've appeared on her show from time to time. She was gracious enough when she had "His & Hers" to have me fill in. I really like Jemele and respect Jemele. I think she’s very smart. She feels very strongly about the issues she speaks on. But that doesn’t mean I'm not going to disagree with Jemele. I disagree with what she had to say. I do think she went too far. It goes back to what I talked about earlier. She’s judging character and intent when actions give you plenty of things to criticize. Some of those, by the way, are outside our sphere.
The president isn't inoculated either, by the way. When those worlds of sports and politics collide, I don’t think the president isn't inoculated from criticism. I think we just have a responsibility to do it in a way that isn't over our skis. Like I said, it's just really dangerous when you indict someone's motives, characters and intentions. This is a conversation that Stephen A. and I have had, on and off the air. I think he does that as well. Let's stick with what they did or said, as opposed to who they are.
SN: But if that's what Jemele truly believes about Trump, and the media's all about free speech, why shouldn't she say what she feels?
WC: Because we have jobs. We have jobs with job responsibilities and expectations of what it is we’re here to do. So Jemele certainly has free speech. We all do. It’s really not a matter of "can’t." It's a matter of "should."
SN: Here's something ESPN's conservative critics may not realize. Do you notice that when ESPNers like Jemele get in trouble, it's usually for something they tweet, not something they said on ESPN air? Does that point to the danger of social media?
WC: Social media is one of my least favorite media platforms. I give, I would guess, 20 times the number of opinions, maybe more, on air every day than I ever do on social media. I have three hours of radio and 15 to 30 minutes a day of "First Take." . . . Certainly on "First Take," we have very sensitive and provocative conversations that push the boundaries of race in America and sports and at times have gotten somewhat political, but I don't feel the need, or the desire, to go to Twitter and share those same opinions. I don't know what it is. I like interaction. I like engagement. My favorite part of Twitter is really the mentions and interacting with people. It’s rarely just the broadcasting of my opinions. I have plenty of other mediums to do that.
SN: You’re a big Cowboy fan. What is going on with Roger Goodell and Jerry Jones? Does this boil down to two rich guys comparing who's bigger?
WC: I think so. I think it's a pissing contest between billionaires. It’s not really about Roger Goodell. This isn’t revenge or retribution from Roger Goodell for Jerry Jones. That's not a fair fight. Roger Goodell can’t square off against Jerry Jones without the backing of multiple billionaires behind him, who want him to go after Jerry Jones. . . . This is a measuring contest between billionaires.
SN: Why do fans love/hate the Cowboys?
WC: They’re America’s Team. That’s just how it is. It makes people live it — and it makes people love them. That is a fact. It was that way before Jerry Jones. It will be that way after Jerry Jones. Tex Schramm set it up in the 1960s. Maybe it’s the star. Maybe it’s the blue and silver. Maybe it was Roger Staubach or Troy Aikman. But the Dallas Cowboys, in my estimation, symbolize what's great about the state of Texas. And what’s great about the state of Texas symbolizes what's great about the United States of America. They are America’s Team.
