1. Vince Carter
Carter is one of the greatest players in franchise history and was at the peak of his powers in the early 2000s. The mutual distaste that Carter and the Raptors had between each other at the time (it has since been patched up) became quite venomous, and it helped knee-cap a half-decade of Raptors basketball.
The feud between the two got nasty, and it very clearly bled onto the court, as Carter appeared to be checked out and giving 50% energy on a good day. Toronto inadvertently hurt his value by letting the trade saga spin out of control. The offer the Nets sent them was laughable.
Vince Carter should have been traded at peak value.
Carter was traded for Alonzo Mourning, but he refused to play for the Raptors. Aaron Williams, Eric Williams, and two picks don’t amount to a very good haul for a game-changer that remains all over the Toronto record books. Acting sooner could have helped Toronto get a much better haul.
While the Raptors did start the Chris Bosh era as a result of this trade, the team’s much-maligned depth alongside Bosh can be attributed, in part, to their feud with Carter, as they managed to tank his value, poison the well, and impact the team on the court.