4. John Spano – New York Islanders
When a new owner comes in, the first thing that fans want to know is, how much money does he have? It quickly becomes clear that they’re more than willing to overlook shady pasts or dubious morals if they’re going to invest heavily in their team. But if they don’t, it’s unforgivable.

Enter Spano. It quickly became clear that all of his promises were lies and that he didn’t have the money for a new suit, nevermind investment in his franchise. Finally, in 1997 the NFL forced him out of the Islanders. Then a court convicted and jailed him twice for fraud.