Despite injury issues throughout his career, Leonard is one of the best two-way wings to ever step on an NBA basketball court, and his legacy with two franchises — the San Antonio Spurs and Toronto Raptors — is secured. Selected No. 15 overall in 2011 by the Indiana Pacers and traded to the Spurs on draft night, Leonard won his first NBA championship in 2014 at age 22, earning Finals MVP honors.