Jackson played point guard for the New York Knicks, Indiana Pacers, Los Angeles Clippers, Denver Nuggets, Toronto Raptors, Utah Jazz, and Houston Rockets in the NBA in a career spanning from 1987 to 2004. After being drafted as the number 18th overall pick in the 1987 NBA Draft, Jackson went on to win Rookie of the Year in his first season and later become an All Star the following season.

Since retiring from basketball, Jackson has also worked as a commentator for ESPN and ABC alongside his former coach Jeff Van Gundy and play-by-play man Mike Breen. He was previously an NBA analyst for The YES Network's New Jersey Nets games and a member of the St. John's University mens basketball team in the 1980s.

On June 6th, 2011, Jackson was hired as the new head coach of the Golden State Warriors.