1. Tracy McGrady
The Raptors took McGrady with the ninth overall pick in the 1997 draft, and he was unquestionably the second-best player in the class. T-Mac was a seven-time All-Star, twice led the league in scoring, and was inducted into the Hall of Fame in 2017. He was an all-time great player that Toronto let slip right through their fingers.
He was drafted straight out of high school and the teenager needed time to develop. McGrady could barely vote by the time his first NBA training camp rolled around, and he still managed to average 7.0 points, 4.2 rebounds, 0.8 steals, and 1.0 block in 18.4 minutes per game. He steadily got better in each of his first three seasons, including blossoming into a starter and helping Toronto make the playoffs in 2000.
The Toronto Raptors should have kept Tracy McGrady.
McGrady was sent to Orlando in a sign-and-trade after their first-round playoff exit. McGrady returned home, but keeping him with Raptors is the biggest what-if in franchise history. He blossomed into an All-Star that averaged 25-plus points per game with the Magic. McGrady and Carter could have formed one of the best superstar duos in the league, and the cousins could have made the Raptors contenders for a decade. Toronto should have done more to keep T-Mac in 2000.
The Raptors much practice patience moving forward when they enter a rebuild. They recognized talent, but they did not always wait long enough to see it through. It is an important lesson to learn and one that could help them moving forward as they try to get back into contention.