Jackson attended Westview High School in the Portland, Oregon area where he was a two-time Metro League Player of the Year and a two-time first-team selection on The Oregonian Class 6A All-State Team.
As a senior at Westview in 2009-10, Jackson averaged 18.6 points, 8.8 rebounds, 2.3 assists, 1.7 steals and made 52.2 percent of his shots to lead his team to the championship game of the Oregon Class 6A division.