The truth was, I immediately saw myself cast in the role of the bespectacled, white, pseudo-intellectual trying to form a "heavy" thesis about a gift of grace and magical flair the black athlete possesses that can never be reduced to anything but poetry. I have always envied this gift and have often said that if I could live life over as someone else it would be wonderful to be Sugar Ray Robinson or Willie Mays. With my luck, however, I would undoubtedly wind up John Maynard Keynes.

— Woody Allen, "A Fan's Notes on Earl Monroe"

There is a moment in the life of every sports fan when you must come to terms with the mathematically irrefutable, yet somehow still surreal fact that the athletes on the court or field or ice are younger than you.1 It's a particularly brutal landmark — youth shifts out from under your feet and the future doesn't seem as limitless as it once did. Some kid is doing something you'll never do and making money you'll never make. For me, that moment came in the spring of 2001, when the chatter around basketball was about a phenomenon named Kwame Brown.

I remember watching a video interview with him around the time of the McDonald's All-American game. Brown, for whatever absurd reason, was seated on a sidewalk in his hometown of Brunswick, Ga. He spoke quietly and under his breath, and rarely looked into the camera. When he was asked how he felt about being possibly selected as the no. 1 pick in the NBA draft, Brown said, "I mean, it's cool, I guess."

There was something about his indifference in that interview — a calcified, defensive indifference — that instantly made me feel connected to him. At the time, I was 21 and trying to figure out whether or not it made sense to graduate from a college that had kicked me out twice in the span of 18 months. When reports started to surface that maybe Kwame didn't really want to be in the NBA, I thought, stupidly, about myself. It doesn't need to be said here that the vast majority of ...