4. Richard “Rip” Hamilton, Shooting Guard
In the 1999 NBA Draft, the Wizards used the seventh overall pick on UConn shooting guard Richard Hamilton, a proven winner who had just led his school to the 1999 NCAA Championship as the Final Four’s Most Outstanding Player. He only started 12 games his rookie year, but as Washington started believing in Hamilton more he would increase his starts, minutes per game, and points per game over the next two seasons.
Michael Jordan joined the franchise for the 2001-02 season and he and Hamilton helped the team win 37 games, 18 more than the previous year. Hamilton started 57 games and averaged 20.0 points per game for the campaign, but unfortunately that would be his last with the Wiz.
Win-now trade leads to big time regrets
In the subsequent offseason, the 24-year-old was shipped off to Detroit in a six-player trade, with Jerry Stackhouse the centerpiece for the Wizards. The win now move did not bear fruit, as Stackhouse failed to lead them to the playoffs while he was there and was off to Dallas just two years later. Washington would win just one playoff series from the time they let Hamilton go in 2002 to Hamilton’s retirement in 2013.
Hamilton, meanwhile, helped lead the Pistons to six straight Eastern Conference Finals in his first six years with the team, averaging 18.9 points in the regular season and 20.8 in the playoffs over that span. Hamilton led the Pistons in scoring during their 2004 NBA Finals triumph over the Lakers, was named to three straight All-Star teams from 2006-08, and had his No. 32 jersey retired by the Pistons in 2017.