Dorothy tells her son he should frequent bookstores because, she says, "that's a good place to meet girls—but don't write that, because then they'll all start hanging out in there."
Derek has his own peculiar screening technique. "One thing he likes to do when he meets a girl is ask very difficult questions," says Douglas Biro, a Tampa-based professional golfer who has been close to Jeter since they met in the fourth grade in Kalamazoo. "He'll ask a hypothetical question, usually along ethical lines. It can be really funny—I've seen women get flustered because they have to play along—but I think he really does it to find out a person's true colors."
"It can be really funny, because the female doesn't have any idea what he's thinking," says Atlanta Braves outfielder Gerald Williams, Jeter's former Yankees teammate. "It's usually about how she would handle a certain situation. He's trying to find out if she would lose her cool and rant and rave, or stay calm and keep her dignity. He's not looking for someone who exhibits extreme behavior, a woman who would bring unnecessary attention to herself, because there's already enough attention [on him] as it is. He wants a woman he can be comfortable with wherever they are, no matter what's going on around them."
Jeter's up in his apartment on a night off, watching Latrell Sprewell and Tim Hardaway go at it in a Knicks-Heat game on TV, when suddenly his eyes drift to his window. "There's someone doing Tae-Bo," he says, gesturing to an apartment across the street. Sure enough, a young woman can be seen performing the trendy workout. "It's a long way from Kalamazoo," he says laughing.
Ask Jeter about his background, and his mood brightens. "You've got to know my family," he says. "My upbringing was like The Cosby Show. We had fun, always did a lot of things together. My parents were involved in everything my sister and I did."
Before every school year Charles and Dorothy Jeter required Derek and Sharlee to sign a handwritten contract that spelled out, among other things, their study habits (daily), expected grades (A's), chores (many), curfew (early) and rules regarding alcohol and drugs (forget about it). "I always tried to negotiate," Sharlee says, "but Derek just sat there and nodded. It was hard having this older brother who did everything he was supposed to do. He had a lot of friends who could do whatever they wanted—stay out late, even the night before a game—but our curfews were always the earliest."
Derek was both sheltered and shy. "When he was 12 or 13, I took him to a basketball camp at the University of Michigan, and when it was time for him to meet the other kids, I had to push him to make conversation," says Charles, a drug and alcohol abuse counselor with a Ph.D., who gave up his practice a year and a half ago to run his son's charitable foundation. "When he was in the eighth grade and was about to switch from parochial school to a public school, we sent him over to the Y to play basketball against older kids as a way of toughening him up. He went, but he took his mother with him."
Now Jeter endorses Coach leather goods, Florsheim shoes, Fleet Bank, Nike and Skippy peanut butter—and the list is likely to grow. "He's doing as well as probably any other player in baseball," says his agent, Casey Close, "and we've turned down a lot of things."
Earlier this year Jordan chose Jeter as the lead endorser for Brand Jordan at Nike. "I love his work ethic," says Jordan, who met Jeter in '94 while playing in the Arizona Fall League during his hiatus from basketball. "He has a great attitude. He has the qualities that separate superstars from everyday people, and a lot of it is attributable to his great family background."
Like Jordan, Jeter has obvious crossover appeal, though it's not clear to which side he's crossing over. The son of an African-American father from Alabama and an Irish-American mother from northern New Jersey, Jeter says that often "people think I'm Hispanic." More important, he tries to pass on his good fortune to others. After his rookie season, Jeter—inspired by his childhood idol, former Yankees outfielder Dave Winfield, who started a foundation for underprivileged children—established the Turn 2 Foundation, which works to steer high-risk kids away from drugs.