Don Juan was born to pimp. The Chicago dandy always had a way with the ladies. Girls at school handed him their lunch money and, after graduation, their welfare checks. "Growing up in the inner city, my role model wasn't no doctor or no lawyer," he explains. "Either I was watchin' some pimp come out with three girls or I was watchin' a dope dealer get into a fine automobile. I tried to work, but it just wasn't in my blood. I considered the pimp game a great trade because I didn't like going to jail. I'd rather send someone else in my place."
Don Juan is one of hundreds of men attending the Players Ball, Chicago's annual gathering of pimps and their stable of prostitutes. The party has been a November tradition since 1974, when bell-bottomed macks or pimps, from Milwaukee and Chicago, first gathered to celebrate Don Juan's birthday with drinking and dancing. "The Players Ball brings people together to recognize that pimpin' is hard work, despite what the public thinks," Don Juan rasps in his whiskey-stale voice.
"The ball appreciates the blood, sweat and tears it takes for a guy with a third-grade education to be driving a Rolls and wearing diamonds." The event, billed as an international competition although foreigners rarely show, is always held at a Chicago nightclub and it is a party, not a pageant. There is no onstage parade of pimps in crushed velvet evening wear, no macks strutting in Speedo swimsuits.
Since Don founded the ball, it's probably no coincidence that he was pimp of the year for 13 consecutive years. The voting process is scientifically arbitrary: A month before the ball, Don and his cronies meet for drinks and argue over which mack made the most money and the biggest name for himself that year. "The criteria for winning is what we call the 365-day-a-year workout," Don explains. "It's all about activity: your bankroll, what kinda car you drive, did you buy a big house, lemme see your jewelry."
Flashy homes, clothes and jewels are how pimps flaunt their success and lure more prostitutes to their stable. "Being named pimp of the year is based on how well you are known and respected, how wise you are to picking up the tricks of the trade," Don adds. "It's like the Academy Awards: If you win, you get more girls, your light be able to shine." To punctuate his words, Don waves cigar-fat fingers weighted by diamond knuckle-dusters that spell "Magic" and "Juan."
In order not to bruise a pimp's peach of an ego, there are many categories: If you're not "No. 1 International Pimp of the Year," you might walk away with a trophy for being a "No. 1 Super Player" or the "No. 1 Boss Player."
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