Kersey attended the then NCAA Division II Longwood College. A virtual unknown coming out of a low-profile school, Kersey was not selected until late in the second round of the 1984 NBA Draft (46th overall pick) by Portland. He became a starter and was part of the nucleus of the strong Portland team of the early 90ís, making it to the NBA Finals in 1990 and 1992. As a Trail Blazer, Kersey was near the top in many of Portland's career categories at the time of his leaving, including games played (second), minutes (third), scoring (third), rebounding (second), assists (sixth), steals (third), field goals made (fourth), and blocked shots (second). In the 1995/96 season Kersey signed with the Golden State Warriors, and the next several seasons would find him with The Lakers, Sonics, Spurs, and Bucks before his retirement from professional basketball in 2001. Kersey served as the Trail Blazers Director of Player Programs in 2003-2004, only to leave the team accepting a assistant coaching position with his former Portland teammate, head coach for the Milwaukee Bucks, Terry Porter.