23. Michael Jordan Drafts Kwame Brown

Dumbass Move By: Michael Jordan
Date: 6/27/2001
Michael Jordan is widely regarded as the best to ever play in the NBA. But when it comes to making basketball decisions, MJ is the furthest thing from the best in basketball. During the 2001 NBA Draft, Jordan used his first overall pick to take a chance on high school prospect Kwame Brown and that decision didn't pan one bit. Brown spent the majority of his time on the bench, battling injuries, or just plane sucking. After a few stints with other teams and nearly a decade later Kwame signed a deal with the Bobcats who are owned by, you guessed it, MJ! Reunited and it feels so...terrible?