His growing profile coincided with a turbulent political stretch for ESPN. Between 2016 and 2018, the network became a regular target of conservative media figures and the Trump administration, which called for the firing of then-commentator Jemele Hill after she referred to Trump as a white supremacist on Twitter. Hill took a buyout from ESPN and now hosts a podcast and writes for the Atlantic.
Some people at ESPN viewed Cain mostly as a shield to that sort of criticism. TV and radio host Dan Le Batard once mentioned Cain by name on the air, suggesting the best way to get hired at ESPN was to be conservative. Others believed he offered important intellectual diversity.
“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 told The Washington Post in 2018. “Will is a great example.”
At ESPN, Cain staked out positions such as Nike’s endorsement deal with Colin Kaepernick was a mistake and that the Washington Redskins should not change their name.
“ESPN doesn’t have a voice like mine,” Cain told The Post for that 2018 story.
Cain felt that voice was plenty valuable to the network, according to people familiar with his recent contract negotiations. Cain, whose last deal paid him in the $500,000 range, asked ESPN for $2 million annually. ESPN executives were interested in bringing him back, discussing a deal worth as much as $1.2 million for a role that centered on his radio show, according to two people with knowledge of the discussions. Cain was interested in hosting a morning radio show, which ESPN was open to discussing but not with him as a solo host. ESPN strongly denied that Cain asked for $2 million or that $1.2 million was discussed; through an ESPN spokeswoman, Cain declined to comment.
In the end, Cain opted to leave for Fox, where his new role is expected to include appearances on Fox News and on subscription streaming service Fox Nation. During his 2018 interview with The Post, Cain said he had no place in the current political debate because he does not support President Trump, which could make for an interesting transition.
The New York Post reported Cain’s upcoming move to Fox News on Monday, after Front Office Sports forecast it this month.
ESPN has much larger concerns, with sports shut down because of the novel coronavirus pandemic. Its parent company, Disney, is also dealing with the impact on its core businesses, from movies to theme parks.
Still, it will be worth watching whether ESPN decides it needs someone to speak to its conservative viewers when social issues arise. Cain’s radio show had momentum, adding affiliates last year in Los Angles and San Francisco, though in recent months he had appeared far less often on “First Take.” One person with knowledge of the decision said it was in part because Cain did not test well in focus groups; another person involved in the show said it was because Max Kellerman, a “First Take” co-host, did not want Cain participating in the show. (ESPN said both theories were incorrect.)
ESPN also has avoided the political spotlight of late, thanks both to the news cycle — President Trump is no longer attacking the NFL and its players — and the network focusing more on traditional “SportsCenter” and highlights during its daily schedule.