Montgomery attended Burns High School in Lawndale, North Carolina, and was a standout in football, basketball, and track. In football, he was a two-time Team MVP, and as a senior, helped lead his team to the State 3A title. In basketball, he won an All-Conference honors and was named the Team MVP. In track, he won All-Conference honors and was the conference champion on the 200 and the 400 meterdash.
College playing career
Montgomery attended Duke University from 1996–99, finishing his career with 171 receptions (ranking second in Duke's history) for 2,379 yards (third), four 100-yard receiving games (seventh), and 13 touchdowns (eighth).