15. Charles Wang, New York Islanders
Wang could almost be replaced here with Maple Leaf Sports Entertainment for their commitment to simultaneously beclown four different sports franchises, but they've recently murmured the right things about using advanced hockey stats. Also, the Leafs aren't moving.
In 2006, Wang used a statistical outlier season to sign a goalie to an astonishingly ludicrous 15-year $67.5 million contract. (The team finally bought out the contract in 2013.) He hired Neil Smith as general manager, fired him 40 days later and replaced him with a backup goalie. For the day-to-day operations, he created an absurd executive structure that routed all personnel decisions through a committee that included non-hockey people who had no idea how to scout, manage or evaluate personnel. Lastly, he's watching the Islanders vacate their home to move to Brooklyn because, aw, shucks, somehow a guy with a lot of money who knew a lot of other people with a lot of money couldn't get an affordable deal worked out. Insert shrugging emoticon here. He's technically still the owner, so Long Island can technically still tell him to fuck off while his franchise chuckles its way to a tonier location.