Age: 58
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?
Best and Worst Sports Executives 2008
There is a whole other game that goes on behind the scenes in any sport. TIME has chosen some of the notable and not so notable sports executives and asks you to vote on who plays the game best