Jackson was undrafted in 1999 following a college career at the University of Detroit Mercy and began his professional career with the Detroit Pistons, going on to play for the Toronto Raptors, Atlanta Hawks and New York Knicks, averaging 2.2 points, 1.1 rebounds and 1.5 assists per game in his NBA career. The Knicks included Jackson in a trade along with Mike Sweetney and Tim Thomas in exchange for Antonio Davis and Eddy Curry of the Chicago Bulls. He was cut by the Bulls on October 18, 2005, and was signed by the Milwaukee Bucks on December 15, 2005. He played for the Bucks in the 2005-06 season, with the team renouncing their NBA rights to him on July 19, 2007. Jackson signed with the Seattle SuperSonics on October 1, and was waived during that month. He also played professionally in the CBA, as well as in Europe for a number of teams, winning the 2004 Italian Cup with Benetton Treviso. In January 2011 he signed with Maccabi Haifa B.C. in Israel. Maccabi released him in March 2012. While with Maccabi, Jackson played in the Israeli Basketball Super League All-Star Game in 2012.
Post-playing career
Jermaine Jackson returned to Michigan after being released from Maccabi Haifa and opened the Jermaine Jackson-Cairns Community Center in Mount Clemens in May. The community center also includes the Jermaine Jackson Academy for youth basketball instruction. Jackson also that year became the boys' basketball coach at Mount Clemens High School. On June 29, 2015 Jackson was named Assistant Men's Basketball Coach for University of Detroit Mercy. After the dismissal of UDM head coach Ray McCallum in the spring of 2016, Jackson was appointed interim head coach until the Titans hired Bacari Alexander who kept Jackson on staff as the lead associate. In late June 2018, Jackson joined SPIRE Institute, a prep school in Geneva, Ohio, as the head basketball coach. During his first season, one of the players he coached was LaMelo Ball, a player who previously played professionally in Lithuania, as well as in his father'sJunior Basketball Association. More recently he has become the young professional LaMelo Ball's manager.
Personal life
Jackson's cousin, Brandon Jenkins, is also a professional basketballer. He currently plays in Switzerland for BC Boncourt. Jackson's son, Jermaine Jr., is also a basketball player who is committed to play at his father's alma mater and former school of employment, the University of Detroit Mercy under head coach and close family friend Bacari Alexander.