8. Rajon Rondo
Today Rondo may be somewhat of a toxic commodity, a fact that arguably nearly ended NBA career in 2016-17. But in 2006 he would have been the perfect backup point guard to Steve Nash during the Suns’ run at a Championship. A steal when drafted 21st overall, the first rounder would have provided depth that not only could have helped out during those playoff trips, but he would have been the perfect replacement for Nash when he inevitably had to leave or retire (If the Suns were still winning instead of losing, is it not possible that rather than trading Nash, he would have played out his final two years in Phoenix and retired here?).
Phoenix traded Rajon Rondo and Brian Grant (who simply retired) for a 2007 first round pick. That player ended up being Rudy Fernandez who they then packaged with James Jones to Portland for cash. To make matters worse, the Suns also traded away their other first round pick, Sergio Rodriguez, and the Rajon pick was one of the two first’s the Suns received in return in the Joe Johnson to Atlanta trade. Thus this trade was doubly bad – not only did they trade away someone who would become a very good point guard and win a Championship in Boston, but they also blew an opportunity to turn that Joe Johnson trade into a steal for themselves.