2001 — Jason Richardson
Wait, Jason Richardson was a bust? Yeah, relatively speaking. Richardson carved out a long relatively successful NBA career, and he remains one of the most underrated dunkers of all time. Richardson scored at least 14 points a game for 10 straight seasons with the Warriors, Bobcats, and Suns. The problem is that Richardson was number five pick and finished his career with only 59 win shares despite all those points and all those seasons.
Richardson was something akin to a replacement player and never really found an NBA home after leaving the Warriors. Golden State might wish they had gone with someone like Joe Johnson or Richard Jefferson in the draft — or maybe Richardson’s college teammate, Zach Randolph.