- Attended St. Johns University. While at St. John's, he played alongside Chris Mullin for one year. He credits Mullin with teaching him the importance of rigorous practice work in the gym.
- Played professional basketball as a Point Guard in the NBA for 17 years with; New York Knicks (1987-1992 and 2001-2002), Los Angeles Clippers (1992-1994), Indiana Pacers (1994-1996 and 1997-2000), Denver Nuggets (1996-1997), Toronto Raptors (2000-2001), Utah Jazz (2002-2003), and Houston Rockets (2004).
- Wears his wedding ring tied to his shoelaces during NBA games.
- Is an ordained minister.
- Jackson was selected as the 18th overall pick of the 1987 NBA Draft by the New York Knicks.
- While playing at St. John's, Jackson had the unusual habit while at the free-throw line of extending his hand and "cupping" his thumb and index finger around the rim. This helped him stay focused on the rim while shooting foul shots. He continued this well into his pro career and it helped him to a career 77.0% free-throw percentage.
- Jackson averaged 13.6 points and 10.6 assists per game in his rookie season, earning him the 1988 NBA 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).
- Was selected as an All-Star player in the 1989 NBA All-Star Game (1989).
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