14. Jerry Reinsdorf
Arguably the most masterful negotiator the sports world has ever seen, Reinsdorf opened a restaurant adjacent to his publicly funded ballpark last year and handed taxpayers a $3.5 million bill. Meanwhile, over the past two years, his charity programs have generously, and quietly, funneled more than $1.5 million into Chicago Public Schools, cancer programs, and children’s charities. Don’t forget about those seven championships, either.
MORE ON REINSDORF: Inside the Start of the Chicago Bulls' Championship Run
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Photograph: Nuccio Dinuzzo/Chicago Tribune