TEAM (YEAR PURCHASED): Toronto Maple Leafs (1994)
W-L (
WINNING PCT): 592-511-89-86 (.463)
 Richard Peddie and Larry Tannenbaum own the Leafs because, well, they could. These fools are filthy rich and have no regard for Maple Leaf hockey. One of the NHL's most storied franchises hasn't won a cup in 43 years and counting and have a winning percentage below .500 since MLSE took control. The Leafs also haven't made the playoffs since the 2003-04 season. Blame Canada? Nah, these dudes are the culprits.