Year: 1981

It may seem like but a small thing compared with some of his other misdeeds, but this first incident was really a harbinger of all the absurd penny-pinching that was to come from the new Clippers owner. Sterling simply tried to renege on a prize he promised for the winner of the contest, assuming (we suppose) that the winner wouldn’t really care.

Unfortunately for the miserly Sterling, contest champion Michael Spilger did care, and demanded the prize he was promised. The Clippers tried to offer him a hotel stay in Puerto Rico, only they decided not to include any other amenities such as airfare or transportation; Spilger finally got his money after a year of wrangling with the front office and threatening them with a lawsuit.