20. Anthony Bennett (2013):
This one might seem obvious if only viewed through the prism of revisionist history, because you could have a rousing debate as to whether Anthony Bennett wasn’t just the worst #1 overall pick since the turn of the century, but one of the worst in the history of the NBA Draft itself. Teams loved the fact that Bennett had a big, strong body at 6’7 and 240lbs, with the ability to out-muscle smaller defenders and “out-quick” larger defenders.
But there were a lot of NBA teams who didn’t even have Bennett ranked among their top five prospects in a rather weak 2013 NBA Draft class, and believe that Bennett was much more of a product of being the #1 pick by process of elimination, since most teams has significant questions about every other player taken among the top picks in that draft.