Jordan transferred to Whitney Young Magnet High School in Chicago for his junior and senior seasons.
He led the Whitney Young Dolphins to the Illinois 4A Championship in 2009, scoring a game-high 19 points in a 69–66 victory over Waukegan.
Upon his 2009 graduation, Jordan was rated by ESPNU as the 60th-best high school senior shooting guard in the country, averaging 10.0 points, 4.5 rebounds, and 3.2 assists per game.
[5] On November 12, 2010, the opening game of the 2010–11 season, Jordan led UCF to victory against University of West Florida scoring a career high 28 points on 8–11 field-goal shooting and 5–7 from the 3-point line.
[16] In 2010, while a college sophomore and underage, Jordan tweeted about spending approximately $50,000 at nightclubs in Las Vegas, prompting an investigation by the Nevada Gaming Control Board.
[24] The same day, body camera footage was released showing Jordan leaving his car parked on a set of railroad tracks at 1:30 am on February 4 in Maitland, Florida, when police found him.