1. Donald Sterling
TEAM (YEAR PURCHASED): LA Clippers (1981)
W-L (WINNING PCT): 830-1,594 (.342)
COMPLEX SAYS: Sterling is a terrible owner and person with a well-documented history that's grimey beyond belief. Racism, sexual harassment, and refusing to pay for medical bills of employees recently diagnosed with cancer? Yup, dude's done just about everything wrong in L.A.. The Clippers have been the laughingstock in sports for a couple decades now. Since Sterling's tenure, the Clips have made four playoff appearances, drafted in the lottery a whopping 19 times, and made notorious draft pick busts like Michael Olowokandi and Benoit Benjamin. Get out while you can, Blake!