I think an historical award needs to go to Ted Stepien, who was such a bad owner that the NBA made a rule to prohibit trading 1st round picks in consecutive years, informally known as the "Stepien Rule". He did such an awful job with the Cleveland Cavaliers that the other owners agreed to give additional draft picks to the Cavs if someone would buy them. Not many owners are so bad that a rule is named after them!
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