18. Kyle Lowry
When point guard Kyle Lowry was selected 24th overall by the Memphis Grizzlies, it was far from a certainty that he would succeed. After all, at 6'0, he is undersized, heavier than most at point guard, and he didn't shoot threes to start his career. That changed when he was dealt to Houston and told he had to shoot them or else he wouldn't play.
His improvement in that regard helped solidify himself as a starting point guard before being traded to the Toronto Raptors, where he became a star. During his nine-year tenure up North, he made six straight all-star appearances and the playoffs in seven consecutive seasons. Had it not been for LeBron James and the Cleveland Cavaliers, Lowry, and DeMar DeRozan might have led them to a couple of Finals appearances instead of being eliminated by the Cavs for three straight seasons.
Fortunately for the Raptors, they acquired star Kawhi Leonard and won it all in 2019, ensuring that Lowry would go down as the greatest player in Toronto history. Lowry would eventually move on to the Miami Heat, helping them make it to the Eastern Conference Finals and NBA Finals. Still, Lowry will always be remembered for his time in Toronto.