1. Kawhi Leonard for DeMar DeRozan
Very rarely can a franchise be said to have convincingly won a trade in which they surrendered arguably the best player in franchise history and acquired someone who would bolt in free agency the following year. However, the Leonard trade remains the most pivotal moment in recent Raptors history.
Leonard only had one year had with the Raptors, but what a year it was. Averaging 26.6 points per game with tremendous efficiency was one thing, but essentially carrying the team on his back during a dominant postseason run made this the best one-and-done season in NBA history.
Toronto Raptors: Masai Ujiri is a champion because of Kawhi Leonard.
While DeRozan had some quality seasons with the Spurs, and Jakob Poeltl has since evolved into one of the best rim protectors in the sport, no Raptors fan would press the reset button and negate this trade if given a chance. Kawhi will always be Raptors royalty as a result of this season.
How many executives would have held onto DeRozan due to his connection with the franchise and concern over Leonard’s future? That willingness to throw all of those factors into the trash and send this trade through shows Ujiri’s savvy evaluation skills.