1. Willie Anderson
Back in 1988, the San Antonio Spurs selected Willie Anderson 10th overall in the first round. Keep in mind, this was a year after drafting David Robinson first overall. Anderson had a solid rookie season where he averaged 18.6 points, 4.6 assists, and 5.1 rebounds while shooting 49% FG. Anderson was named to the NBA All-Rookie First Team after an impressive NBA start.
Over the next few seasons, his numbers started to drop little by little. Anderson spent seven seasons with the Spurs, where he averaged 13.2 points, 4.2 assists, and 4.0 rebounds. His numbers were still decent, but for someone selected 10th in the first round, you'd look forward to a more solid contribution.
After his San Antonio stint, he became part of the expansion draft for the Toronto Raptors, where he played for one season. He played with the New York Knicks and the Miami Heat for a season, respectively before playing overseas.
By taking Anderson, the Spurs missed a chance to draft Dan Majerle, a three-time All-Star, who was selected by the Phoenix Suns with their 14th pick.