On Simmons’s rise, his gripes, and Grantland.

It was a sultry afternoon, and midway through the game, we went inside to the Dugout Club to cool off and talk. Simmons sounded as if he was having some regrets about Grantland. “It hasn’t been as much as fun as I had thought,” he told me. “I’m not sure I would do it again.” Too much of his time was being spent in the office, dealing with administrative tasks, which was encroaching on his column.

Simmons’s literary persona suggests a slacker, a guy who would like nothing more than to spend his days drinking beer and watching sports. This image, enhanced by his loose, casual prose, is misleading. The real Simmons is hard-working and competitive. His rise to prominence has been punctuated by bouts of restlessness and frustration, even when things looked from the outside to be going his way. He’s still chafing over his publisher’s handling of his 2009 book, “The Book of Basketball,” a No. 1 New York Times best seller.

Going back-back-back through the years with ESPN’s Chris (Boomer) Berman:

And then he’s talking about how deeply the New England Patriots have bought into the philosophies that have brought them two of the last three Super Bowl championships. “I mean, they’ve really drunk the Kool-Aid there,” he says, referencing a mass suicide about which we all learned on television. “What do you suppose it was?” he continues. “Goofy Grape? Jolly Olly Orange?”

He knows the names of juice-drink flavors. He still knows the names because he learned them on television, because we invited it in and it never behaved the way it was supposed to behave.

O.K., you’re a sensible person, so he can make your head explode.

On Keith Olbermann’s rise and fall at ESPN; an excerpt from the Those Guys Have All the Fun, an oral history of the network.