Miles came to Southern California from Stockholm, Sweden and became a HS All-American at Mater Dei. He played for Gary McKnight, where he won four CIF titles, a rarity in CIF history. Miles then went to Arizona where he led Wildcats in an All-American career to their only NCAA title in 1997 when the Wildcats upset three #1 seeded teams. He was named NCAA Tournament MVP when he averaged 22 ppg in the six tournament games. The 6-5 guard had a limited NBA career, but while playing in the CBA, he was named MVP and Playoff MVP and set a league record by making 60 straight free throws. He also played professionally in Europe for 6 years.

Simon then turned to coaching and was an assistant for Lute Olson for three years at U of A, including going to the NCAA Elite 8 one year. He also worked for many years doing television broadcasting before going to the Los Angeles Lakers in 2017, where he is currently an assistant coach.