After a frustrating stint at the Boston Herald, Simmons comes across The Boston Movie Guy, a movie reviewer for AOL’s Digital City Boston. They should have a Boston Sports Guy, he thinks, and begins badgering the site’s editors. For $50 a week, the job is his. In time, his Sports Guy columns earn him a cultlike following and, years later, a national gig writing columns for ESPN’s sports and pop culture site Page 2.
A loyal reader, Kimmel recruits Simmons to write on season one of Jimmy Kimmel Live!
Simmons turns his popular columns into a best-selling memoir on Red Sox fandom. In 2008, he publishes his second book, a tome on the history of the NBA that shoots to the top of the New York Times best-seller list.
He begins building his empire, which includes the 30 for 30 series and a podcast network.
Simmons launches Grantland, what he sees as the crowning achievement of his ESPN tenure. When he leaves, the since-shuttered sports/pop culture site has more than 50 writers. Profitability, he says, never is a top priority: “Skipper would be in these meetings saying, ‘I don’t care if Grantland makes money. We make $7 billion a year. Stop worrying about that stuff, I want you guys to be Rolling Stone in the 1970s.”
His TV career begins in earnest with a gig on NBA Countdown. He also pops up on ESPN’s PTI.
Simmons’ 14-year run comes to an abrupt end May 8, when Skipper announces via the New York Times that ESPN will not re-up the firebrand. “They did it in a way that was obviously designed to try to embarrass me,” he says, “and to be petty assholes.” Months later, he relaunches his podcast business, for which he’s intimately involved in recruiting sponsors. On June 1, he adds sports/pop culture/tech site The Ringer.
On June 22, HBO debuts Any Given Wednesday, a pretaped talk show featuring Simmons’ interviews and POV. HBO also will offer his podcasts and of-the-moment opinions in video form on HBO Now.