Michael Olowokandi, Clippers (1998)
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The 1998 NBA draft featured two guys who won NBA Championships and will almost certainly be headed to The Naismith Memorial Basketball Hall of Fame (Dirk Nowitzki and Paul Pierce), as well as a high-flying superstar that took the league by storm (Vince Carter). Yet, the Los Angeles Clippers missed out on all of those guys, when they took Michael Olowokandi with the first overall pick in said draft. Between Olowokandi never really reaching his potential, and eventually being limited due to injuries, he goes down as one of the biggest draft disappointments in NBA history.
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