Webb was born into poverty in Dallas, Texas. He was raised in a small two-bedroom home and used basketball as an inspiration. Webb was not tall, but he used his quickness and jumping ability to outplay the other, bigger kids. Starting in the seventh grade, Webb was told that he was too short to play basketball. He received a chance to play on his junior high team only after 2 players forgot to complete their physical exam requirements in time for the first game. Webb scored 22 points in that first game. He could dunk the ball when he was 5 feet 3 inches (1.60 m). At Wilmer-Hutchins High School, he played on the junior varsity team where he made a large impact; when he made the varsity team, he averaged 26 points per game.\n', '

Despite his impressive high school record, colleges showed little interest in Webb. He received his first opportunity to play on a college basketball team when he attended Midland College (in Midland, Texas), where he led the Chaparrals to the junior college national title in 1982. In the championship game, Midland defeated #1-ranked and previously unbeaten Miami-Dade North of Florida, 93 to 88, in double overtime. Webb led all scorers in that game with 36 points, making 10 of 15 shots from the floor and 16 of 18 from the free-throw line. His performance at the tournament earned Webb a write-up in Sports Illustrated, and national attention. In 1983, he was named an NJCAA All-American by the National Junior College Athletic Association.\n', '

Webb attracted the attention of Tom Abatemarco, an assistant coach at North Carolina State University, who arranged for Webb to meet head coach Jim Valvano, who offered Webb a scholarship. In college, his vertical leap was measured at 42 inches (1.1 m).\n', '

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