Jackson had a steady career with the Knicks, most notably under coach Rick Pitino, averaging 13.6 points and 10.6 assists per game in his rookie season, earning him the 1988 Rookie of the Year award, the lowest overall draft pick to win the award since Woody Sauldsberry in 1958. He was the only non-lottery pick to have won the award since the introduction of the system in 1985 until the 2016-17 season, where Malcolm Brogdon won the award as a second round pick.