6. DeMarre Carroll
Carroll was a late first-round pick in 2009 that bounced around the league early in his career. He played for four different teams in four years before finally getting his first significant opportunity with the Hawks in 2014. He quickly became a starter and key rotation piece that helped Atlanta reach the conference finals in 2015.
The Raptors swooped in and signed him as a free agent after his run with the Hawks. Toronto had made the playoffs two straight years, but they were searching for their first postseason series win since 2001. Carroll helped the Raptors reach the conference finals in his first season in Toronto.
DeMarre Carroll struggled with the Toronto Raptors.
The 6-6 wing only lasted two seasons with the Raptors before being shipped to Brooklyn in one of the worst trades in franchise history. Toronto gave up Carroll and two draft picks for Justin Hamilton, who they immediately waived and stretched. Cap space was created, yes, but Carroll blossomed as soon as he left.
Carroll was a quality rotation piece for the Nets for the next two seasons, averaging a career-best mark in PPG in his first Nets season. He could have helped the Raptors in 2018 as they were swept by the Cavaliers in the second round of the playoffs.
Toronto won the championship in 2019 as Carroll began to decline in Brooklyn. The 36-year-old has not played in the NBA since 2020, but the Raptors sold just a bit too soon.