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ESPN The Magazine: Theo Epstein, The Mastermind

I'm happily rooting for the Cubs in the postseason ... until they meet the Red Sox in the World Series.

Epstein knows how others see him, and he's self-aware enough to both understand his reputation and mock it. His friends are always baffled at his image as a cold exploiter of markets and inferior systems. One night this summer, the owner of the team, Tom Ricketts, held court at a charity boxing match and explained that few people are as different from their public narrative as Theo: He gets painted as a quant, while his attachment to baseball is actually deeply emotional.