Chicago Blackhawks
One thing is certain: it’s never boring to be a Blackhawks fan. Bill Wirtz turned them into the laughingstock of the 2000s because he refused to pay their best players. He also blocked TV crews from filming live home games because he thought it was unfair to season ticket holders (via The Hockey Writers).

This was ludicrous behavior but eventually, old Bill aged out of significance. His son turned things around and the team won a Stanley Cup in 2015. But then they went back to their roots and showed that some things stay the same in this world. The Blackhawks are a bad team again and an embarrassment to hockey.