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Tom Ricketts

Age: 50

Occupation: Chairman and co-owner, Chicago Cubs

Ricketts owns one of the most powerful sports brands in the universe. And when the Cubs finally play well, the world will likely be watching—and buying—as much of the team as it can. But five years into the Ricketts era, the team enters this season on the heels of the worst two-year record in its history (127 wins, 197 losses). For a franchise that hasn’t won a World Series in over a century, that’s really saying something. Ricketts spent much of 2013 on another just-as-vexing project: negotiating with neighboring rooftop owners over a planned $300 million renovation of his stadium.