Bad-Boy Pitchmen

Shoe marketers trying to reach trendsetting young urban males have discovered a fact long known by any weary eighth-grade teacher: guys love a troublemaker. Celebrity endorsers typically have been squeaky-clean family men like Cal Ripken Jr. or harmless rebels like long-haired Andre Agassi. But today's sneaker ads often showcase figures known as much for alleged misdeeds as for their accomplishments. When a company attaches its brand to these antiheroes, "it's a way of saying, 'We're in touch with somebody who is street real,'" says Rick Burton, professor of sports marketing at the University of Oregon. And it's a way of accomplishing...

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