- Sunrise Sports and Entertainment, Florida Panthers: The Florida Panthers surprised everyone by making the playoffs this year, their second playoff appearance in fifteen years. Florida was the first NHL team in history to miss the playoffs for nine consecutive seasons in one city. There are constant talks about the Panthers relocating with the team mired by a history of attendance issues. The ownership is even $99 million in the red, bleeding money from the franchise. At least they make money for every other event held in BB&T Center, though.
- Josh Harris, New Jersey Devils: This once-proud franchise is also having financial problems, owing the NHL $230 million in debt at one point. The NHL is close to taking over the team, but that's not the only issue that has Devils fans seeing red. Harris landed in a helicopter in the middle of a kid's soccer game, prompting the wrath of many soccer parents in the Meadowlands.
- Maple Leaf Sports and Entertainment, Toronto Maple Leafs: It's been a looooooooooong time since the Maple Leafs last won the Stanley Cup. In fact, the Blue Jays have brought Toronto their most recent title, winning two World Series titles in the 1990s. The Maple Leafs have only one playoff appearance in the last eleven seasons, with their only appearance being a Game 7 chokejob to the Boston Bruins. The most points the Maple Leafs have amassed in the past 11 seasons is 91 in 2006-2007... And they still missed the playoffs. Attendance is still great, but it seems that the ownership only cares about money and not winning.
Honorable Mentions: Predator Holdings LLC (Nashville Predators), Daryl Katz (Edmonton Oilers)