Title: Principal owner, Boston Red Sox
PRO: One curse-busting championship was enough. But a second? Beatified in Beantown, he has also introduced a new sports ownership model by creating a conglomerate that owns the Sox, a television network, Fenway Park, real estate and a 50% stake in a NASCAR team.
CON: With their free-spending ways, the super-rich Red Sox have completely lost their charm. Have they turned into an "evil empire" like the Yankees?