11. DeMarre Carroll
Carroll was a late first-round draft pick in 2009, but he struggled to find a consistent role early on. The 6’6 wing showed flashes during his first four seasons in the league, but it was not until he joined the Hawks in 2013 that he blossomed. Carroll was a starter on the wing on back-to-back playoff teams, including in 2015 when they reached the conference finals.
Carroll became a free agent after that run. He was right in the middle of his prime, and he agreed to a four-year $60 million deal with the Raptors. The 6’6 wing was a key rotation option, but his new contract made him the 41st highest-paid player in the 2015-2016 season.
He struggled to stay healthy in year one, and his efficiency dropped off significantly. Still, the Raptors reached the conference finals. Carroll did not make the same impact in Toronto. In year two, his production slipped further, and it became clear the Raptors needed to move on.
Toronto had to trade one first-round draft pick and one second-rounder to Brooklyn for the Nets to take on Carroll’s contract. It was a disastrous signing, and the 6’6 admitted to not fitting into the Raptors’ iso-heavy offense after his departure. It was a move fans would love to forget happened.