New York Knicks (1987–1992)
Jackson was the 18th pick of the 1987 NBA draft by the New York Knicks. He teamed with Patrick Ewing and Charles Oakley to turn the Knicks into a prime playoff team in the late 1980s and early 1990s. However, before the Knicks peaked and became regular playoff contenders, he was traded to the Los Angeles Clippers in 1992.
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.
In 1989, Jackson had another promising season for the Knicks, teaming with Ewing to lead them to the Atlantic Division title and the number-two seed in the East (behind the eventual champion Detroit Pistons, whom they swept 4–0 in the regular season), and making his lone All-Star Game appearance. After sweeping Charles Barkley's Philadelphia team in the opening round, the Knicks faced the upstart Chicago Bulls, led by Michael Jordan, in the Eastern Conference semifinals. Near the end of Game 2, Jackson en route to a fast-break layup in the fourth quarter looked back and stuck out his tongue at Jordan before finishing the layup; Jordan responded with a 40+ PPG average the remainder of the series, and led Chicago to a 4–2 series victory.
Following a contract extension prior to the 1990 season, Jackson began to lose his All-Star form; the loss of Pitino (who left to coach the University of Kentucky) and starting the season out of shape were key factors. Consequently, he faced stiff competition from backup guard Rod Strickland, and after Strickland was traded away, Maurice Cheeks, to the point where, in their decisive first-round Game 5 against Larry Bird, Kevin McHale, Robert Parish, Dennis Johnson, and the Boston Celtics at the Boston Garden, Knick coach Stu Jackson benched Jackson for the entire game New York defeated Boston to advance to the second round, where they lost to the eventual champion Detroit Pistons in five games.
