18. Gary Bettman
Bettman is the first of several Major League commissioners on this list. He is arguably the least successful of any of them even though hockey is arguably the most exciting sport. It is so fast-paced and has incredible action but Bettman’s reign has seen viewing numbers decline in key areas. He focused on the Sun Belt because of the lucrative revenues there than in loyal hockey markets.
Meanwhile, he oversaw three lockouts. One of these resulted in the write-off of an entire season. In short, this was an absolute disaster. As a result, many hockey fans loathe him. Like all of the shadiest sporting figures, money is everything to Bettman. It’s not about delivering a great product but gaining a major profit. But this is short-term thinking.