I'm watching a classic 1988 Bulls vs. Pistons game (first aired on April 3, 1988) on NBA-TV, and I figured out why Jordan shaved his head the following summer. In this game, Jordan still has his normal hair, but is rapidly thinning in front. Somewhere buried on the Bulls bench (and playing a few minutes in 1st Q/2nd Q) is a center Granville Waiters, who had an advanced state of male pattern baldness, as much as Bozo the Clown in fact.
I'm sure a young Jordan, razzing Waiters one day in practice suddenly realized that he might be next, and decided to shave his remaining hair off to avoid the embarrassment. Perfectly logical.
update, rewound the TiVo, and Waiters definitely was the guy that started the trend. See this photo. Nuff said
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Waiters, as a Rocket.
Jordan's Hair Trigger, as it were. Ahem.