Most scouts predicted that Webb would end up playing in either Europe or for the Harlem Globetrotters because of his height. However, Webb was drafted in the 4th round of the 1985 NBA draft by the Detroit Pistons. His first six seasons were played with the Atlanta Hawks before he was traded to the Sacramento Kings for Travis Mays, where he had his best years statistically and played as a starter from 1992–1995. Webb posted career highs of 16.0 points and 7.1 assists per game in his first season with the Kings. He also led the NBA in free throw shooting in his last season in Sacramento, shooting 93.4 percent in 1994-95 (after shooting 81.3 percent the previous season).