Bill Simmons Won’t Move Back to Boston at Gunpoint

Or so says Jimmy Kimmel in a new Rolling Stone profile of the Boston Sports Guy.



When Bill Simmons left Boston to write for Jimmy Kimmel’s show in Los Angeles back in 2002, he—the Boston Sports Guy—had a lot of explaining to do. Thankfully, this is Bill Simmons we’re talking about, and emoting over the goings-on of his personal life is sort of his thing.

“Ride through Cambridge on Memorial Drive and gaze across the Charles River, and there’s Boston … Each time I hit that stretch, I thought to myself, ‘I can’t believe I’m here,'” he told his ESPN column readers just after his departure. His ode to the city, titled “Sadness is Boston in My Rearview,” ended on a promise:

“I left my heart in Boston, along that stretch of Memorial Drive. Some day, I’ll go back to get it.”

Perhaps you’re still boycotting Simmons and didn’t notice, but there’s a great new profile of him in Rolling Stone. It describes the making of his now-significant media empire and gives the sense that, if ever he did return to Boston to get his heart, it was only to haul it back to Los Angeles.

“I don’t think you could get him to go back to Boston at gunpoint,” Jimmy Kimmel tells reporter Rob Tannenbaum. The piece suggests that this is, in part, because of Simmons’s complex relationship with the city. His brand is based on an unapologetic, rabid love for the teams. But “Boston is where I failed,” he notes.

And sure, the contours of this rise from the ashes are familiar to any Simmons reader because, again: Bill Simmons. He got his first job working for the Herald, but he was writing about high school teams and doing grunt work while, in his words, ” mediocre writers were blocking my way.” So he left and started blogging for This appears to have been a good gamble.

Beyond origin stories, though, the rest of the piece gets at what Jimmy Kimmel probably meant about Simmons’s aversion to returning: The guy’s just got a lot going on. He runs a website, hosts a podcast, produces a TV show, writes bestselling books… “It’s the sportswriter version of the EGOT,” Tannenbaum writes. The need to be in the city he has long rooted for seems superseded by business interests.

To read Simmons talk about his love for the city suggests that Boston is still in his rearview, but in this case, it may actually be further than it appears.