24. Bill Wirtz – Chicago Blackhawks
Under Rocky Wirtz, the Blackhawks are a rejuvenated franchise. They’ve won three Stanley Cups under his reign in charge. This is a far cry from the days of misery under his father Bill. During the elder Wirtz’s tenure, ESPN named the Blackhawks the worst franchise in the US.

He ran them into the ground and made several inexplicable decisions. Wirtz refused networks that wanted to televise home games. That’s because he thought home attendances would drop. Furthermore, he was notoriously stingy with his purse strings too.