Reginald Shon Jackson entered the world on April 16, 1990, in Pordenone, Italy, where his father was stationed with the U.S. The family later moved to Colorado Springs, Colorado, where Jackson attended General William J. He earned the 2008–09 Gatorade Colorado Player of the Year honor before playing three years of NCAA basketball at Boston College. His progression peaked during his junior season, when he posted averages exceeding 18 points per contest and declared for the NBA Draft following the 2010–11 campaign. Jackson requested more playing time and was dealt to the Detroit Pistons in February 2015. He quickly proved his value, leading Detroit to the playoffs in 2016 with a stretch of double-double performances in points and assists. However, injuries and performance inconsistencies gradually reduced his influence with the Pistons over time. After finalizing a buyout with Detroit in 2020, Jackson joined the Los Angeles Clippers and enjoyed a career renaissance.