For Bill Simmons, the walk on Laker game days from his office at ESPN to the Staples Center — or “the Silicon Center,” as he once referred to it in a column — is an excruciating 250 yards, a nauseating gantlet of purple and yellow jerseys, T-shirts and banners that choke L.A. Live, the cheesy outdoor plaza that Kobe built. The games themselves are a special kind of sports abomination to him — more Hollywood scene than sports event, where no one gets drunk and yells at the officials, where the crowd could easily be mistaken for the audience at a Coldplay concert (his metaphor) and the loudest cheers are for Jack Nicholson.

Simmons is the most prominent sportswriter in America. He’s also a Boston fan. During his early years as a columnist in the late 1990s and early 2000s, he was sustained by the angst of backing losers, above all, the Red Sox. More recently, with Boston’s various sports franchises prospering, he has sought poetic inspiration in the teams he hates, and, with the exception of the Yankees, he hates no team more than the Lakers.

“It’s sad how well I know this place,” he told me as we entered the arena on a Wednesday evening in early May, a few minutes before tip-off at the Lakers’ second playoff game against the Dallas Mavericks. We arrived at our seats near midcourt just in time for the pomp of pregame introductions. A huge white sheet covering the video screen dropped to the floor, and the strains of the Who gave way to the absurdly dramatic voice of the P.A. announcer: “The defending back-to-back N.B.A. champions, your Los Angeles Lakers!”

ESPN’s press presence at N.B.A. games is dominated by men who, in their slick suits and Italian loafers, seem to be taking their misguided fashion cues from the players themselves. Simmons, who is 41, was dressed more like a TV comedy writer — which he was, briefly, on “Jimmy Kimmel Live!” — in a T-shirt, Jack Purcell sneakers, a baseball cap and blue jeans.

During the...