5. Chauncey Billups
Before he was Mr. Big Shot, Billups bounced around the league. He was drafted third overall in 1997 by the Celtics, but his tenure in Boston lasted just 51 games before being dealt to Toronto. The 6’3 guard played just 29 games for the Raptors prior to being traded to Denver.
His time with the Nuggets was disappointing. He played in just 58 games over two seasons and was traded to Orlando after suffering a season-ending shoulder injury in 2000. Billups looked like a draft bust after struggling to stay healthy and produce consistent numbers after three years in the league.
Billups signed with the Timberwolves in the 2000 offseason to be their backup point guard. When starting point guard Terrell Brandon suffered a season-ending injury, Billups got the chance to start and broke out. He joined the Pistons in free agency in 2002 where he became an All-Star and led Detroit to the championship in 2004.
The Pistons traded Billups back to Denver in 2008 for Allen Iverson, and he helped the Nuggets reach the conference finals in 2009. Imagine if the franchise had kept him back in 2000. Chauncey Billups likely would have ended their playoff drought sooner and significantly improved their postseason chances in the mid-2000s.
Denver gave up on the five-time All-Star way too soon, and they were ecstatic to get him back nearly a decade after trading him away.