Scottie Pippen took the long road to the NBA. He walked on to the University of Central Arkansas, an NAIA program. Despite that, Pippen played all four years, earned All-American honors, and drew the attention of some scouts.
Pippen was drafted with the 5th overall pick in 1987, and the rest is history. One of the first things Pippen did when he got that NBA contract? Buy the house his parents lived in outright so they wouldn’t have to worry about the mortgage. He went on to earn over $100 million in his career.