He smiled and looked at his co-worker: “Do you hate me?” he asked.
Was he just needling? Or was this a glimpse into ESPN’s new business model? Cain is a 43-year-old Texan who has worked for right-wing luminaries — for Bill Shine (now a senior White House staffer) at Fox News and for Glenn Beck at The Blaze. On CNN, he used to debate Eliot Spitzer on policy questions like whether health care is a right. (It is not, Cain says.)
Now he is a rising star at ESPN, where he dukes it out with Stephen A. Smith and Max Kellerman on “First Take,” in addition to hosting a solo national ESPN radio show every afternoon.
Cain’s growing profile comes amid consistent charges of liberal bias at ESPN for its coverage of social and political issues in sports. Last month, President Trump sent out a fundraising email after ESPN announced it would not show the national anthem during “Monday Night Football” broadcasts this season, accusing the network of a “spineless surrender to the politically correct liberal mob.” (The network was continuing its past policy.)
With his conservative bona fides, Cain may offer much-needed intellectual diversity at a network that leans left. Or he could be a sop to conservatives at a network desperate to quiet its critics, including those in the White House.
Or, maybe, Cain’s just good on TV.
Regardless, if ESPN needs a voice to say that football players should stand for the national anthem, or to explain why Nike is making a mistake by attaching itself to Colin Kaepernick, Cain is the guy. The Washington Redskins should not change their name, he has said, asking, “What’s the level of offense we’re willing to tolerate in society?” After Serena Williams’s recent dust-up at the U.S. Open, he joked on the radio, “This is about the long fight for women’s rights against that known and traditional foe: tennis umpires.”
“Has being conservative helped me since I’ve been here?” Cain said. “Of course. ESPN doesn’t have a voice like mine.”
'A potpourri of opinions'
On “First Take,” Cain’s voice — his right-leaning takes and his lilting Texas twang — stands in sharp contrast to Smith and Kellerman, both New York City natives. And it often makes for good TV.
“We want a potpourri of opinions,” Smith said. “I’m interested in mass appeal for the show.”
Kate Fagan, an ESPN writer who has hosted with Cain, said: “He hasn’t changed my mind on any one issue; he’s been more impactful. Will was my first foray into getting out of my own echo chamber and radically changed how I looked at stories.”
There is little doubt that ESPN has been progressive on issues like gender and race — the network honored Caitlyn Jenner after she came out as a transgender woman and launched a website, The Undefeated, devoted to covering the intersection of race and sports. Notable personalities have been critical of Trump on social media; Jemele Hill, who recently left the network, called him a white supremacist, prompting a rebuttal from the White House. The political critiques of ESPN have come as the network confronts larger industry trends, such as cord-cutting, which has led to layoffs. Whether that means ESPN needs a Will Cain to balance its ideological ledger depends on whom you ask.
“When I look at this topic — the criticism that we’re left-leaning — my job is to bring on people who have different thoughts,” ESPN President Jimmy Pitaro said. “Will is a great example. . . . I feel like we’re pretty balanced right now.”
Pitaro, who has been in his new job for six months, has also made clear that ESPN shouldn’t be in the politics business. “If you ask me is there a false narrative out there, I will tell you ESPN being a political organization is false,” he said over the summer.
On Pitaro’s watch, the 6 p.m. “SportsCenter” and morning show “Get Up!” have emphasized traditional sports content. But Pitaro’s charge may be as much about perception — and making sure that ESPN isn’t seen as a liberal outpost by its most zealous critics. Robert Lipsyte, a former ESPN ombudsman, said the network is no different than Twitter or Facebook.
“I don’t think they’re a liberal network,” he said. “But the conservatives complain, and they want to appeal to as many people as they can.”
If that’s the case, it doesn’t hurt to get someone like Cain in front of as many eyes as possible — and also on “First Take,” sponsored by Bass Pro Shops.
Smith did not hesitate when asked what he liked to debate with Cain. “The social and political issues,” he said. “If it’s a sports conversation, he can’t hang — it’s like a train running over somebody.” Several ESPN staffers privately expressed a similar sentiment, believing Cain’s perceived value to ESPN’s higher-ups was based on nothing more than his politics.
Last year, ESPN TV and radio host Dan Le Batard name-dropped Cain when he suggested that the best way to get an on-air job at ESPN was to be a conservative. And after the Trump administration introduced a travel ban that targeted Muslim-majority countries, ESPN radio staff received an email offering Cain to provide balanced commentary on the issue. (The memo was first reported by Deadspin.)
“I had nothing to do with that,” Cain said of the email. “I think there are presumptions people make because of my point of view.”
From politics to sports
Cain grew up north of Dallas and cut his teeth in the media business. After law school at the University of Texas, he took a $19,000 job near Austin, covering local news — and also delivering the newspaper.
Always the entrepreneur, he bought a string of small-town papers and started a magazine that catered to the quinceanera market. One story sticks with Cain from his shoe-leather reporting days: He covered a suicide just a few years after his father took his own life, which instilled in him an outlook similar to that of Ben Shapiro, the conservative commentator.
“The news is the news,” Cain said. “Facts don’t care about your feelings.”
The failure of liberals, Cain said, is the hubris to believe “you can organize more than you’re capable of actually accomplishing.” On climate change, for example, he does not believe in society’s “ability to re-engineer an economy to regulate the level of temperature in society.”
After selling the papers for a tidy profit, Cain moved in the late 2000s with his wife to New York — where he still lives — and tried to break into the media world as a voice on the right.
He filmed a pilot for a TV series, a roundtable political discussion inside an Upper West Side deli that included Kevin Williamson, the conservative writer, and Chris Hayes, now an MSNBC host. The show never materialized, but Cain hustled his way into hosting a video series for National Review and was introduced to Shine, who helped him get booked on Fox News as a pundit.
He made appearances on “The View” and MSNBC, and pitched himself to CNN, while also earning a regular role on a TV show on The Blaze. Rob Savinelli, an ESPN VP for recruitment, saw Cain on CNN, and despite his lack of a sports background, pushed to hire him. “I sat in front of executives and talked about what sports meant to me — from playing to my fandom,” said Cain, who had walked on to Pepperdine’s water polo team.
He initially did features on “Outside the Lines,” the network’s news magazine (he rode a bus through Mississippi with a minor league baseball team) before filling in on “First Take.” Last year, Cain was tapped to co-host afternoons on ESPN radio, and when co-host Ryen Russillo left the show, Cain suddenly was riding solo. His show debuted in January; it reaches some 200 terrestrial stations and averages a million listeners per week.
Cain is sensitive to the critique that he is politics-first and likes to note that he arrived at ESPN before the network was in Trump’s crosshairs. “I didn’t come here to bring politics to sports,” he said recently on his show. “I didn’t come here to counterbalance anybody out.”
He compares himself with Philadelphia Eagles General Manager Howie Roseman, who got his first job in football after law school, with no football background.
His first sports memory is watching Dwight Clark catch the winning touchdown pass in the 1982 NFC championship game. “I was 6, and I cried,” he said. Cain remains a die-hard Dallas Cowboys fan, and he sees sports as an escape from politics.
“A lot of tribalism we want to stamp out — racial tribalism, for example,” he said. “But I love that Boston fans are Boston fans, and Texas fans are Texas fans. God help us if we all become the same.”
Cain said he has no place in the current political debate — he does not support Trump — and although his show sticks mostly to sports, politics still animate him. Following college football’s opening weekend, Cain suggested Miami was in bigger trouble than Michigan or Texas after all three lost. But he sounded more passionate analyzing Nike’s new Kaepernick ad, arguing the former quarterback’s cause was “washed under a flood of capitalism.”
'These are big boy rules'
Cain held court over that dinner in Bristol. Of the ongoing NFL protests, he said, “I try to think I’ve listened with a critical ear, broadly about social injustice and more narrowly about racial injustice.”
“Now it’s like a married couple fighting,” he added, referring to Trump and the players.
Cain also expressed admiration for Clay Travis, the controversial radio host who has relentlessly attacked ESPN’s politics while popularizing the “MSESPN” insult. “I think he sees things in ways that are fairly unique and brave,” Cain said.
ESPN, of course, has had issues with its outspoken conservative commentators in the past. Rush Limbaugh resigned in 2003 after he said Eagles quarterback Donovan McNabb was overrated by a news media that wanted to see a black quarterback succeed. Curt Schilling was fired for a series of racist and homophobic comments.
If today’s political right has prized a willingness to troll the left, Williamson, a writer for National Review, said there is an earnestness to Cain. “There’s a model of discourse that rewards anger and outright rage and oversimplification,” he said. “Will is more interesting in his political presentations.”
Lipsyte put it another way: “He’s not so obviously a nut.”
As Cain’s visibility has increased, Smith has seen his colleague shaken by being called a racist and a bigot on social media (Snoop Dogg called him “a f------ devil” after a “First Take” segment about the Redskins’ name.) Six months ago, Smith pulled his colleague aside.
“I said these are big boy rules,” Smith said. “You are going to have people that attack you, and you have to accept it comes with the job.”
Cain appreciated the advice.
“No one wants to be called a racist if you’re not one,” he said. “Anybody who tells you they don’t care about being liked is lying.”