By his own admission, Brad Gilbert was not the most talented tennis player. And yet, across the span of his sporting career, he accumulated $5.5 million in prize money, and achieved a career high world ranking of #4, along with twenty singles titles and an Olympic bronze medal. By almost anyone’s account, that is a successful career—so how did Gilbert, who on paper, should have been a middle of the pack player, achieve so much success? As he points out in his book, Winning Ugly, it’s because tennis matches aren’t played on paper, they’re played on a court, between real people—and people can be gamed.
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