6. Jeffrey Loria

In just three years of owning the Montreal Expos, Loria managed to alienate pretty much every remaining fan of the beleaguered team, as well as Montrealers who otherwise couldn't have cared less about the Expos. Between 1999 and 2002, Loria neglected to reach agreements on broadcast rights for games, gutted the roster, and attempted to use the team as a bargaining chip in a bid to get government money for a new stadium. When that failed, Loria negotiated a lucrative agreement in which he sold the team to the league at a hefty profit and gained control of another franchise, the Florida Marlins.