A shooting guard-small forward from the University of Oregon's Ducks, he was chosen in the 2008 NBA draft by the Phoenix Suns, who then traded him to the San Antonio Spurs.

Hairston and his teammates Maarty Leunen and Bryce Taylor became three of the eleven players in Oregon history to record 1,000 career points as juniors.

Injuries slowed his production in 2006–2007 but Hairston was instrumental to the Ducks' late-season run and Elite Eight appearance in the 2007 NCAA Division I tournament.

[4] During his college career he grabbed 12 rebounds on two separate occasions, the first in a 58–56 loss to Stanford on February 26, 2005,[5] and in an 88–54 win over Idaho State on December 17, 2006.

[6] He closed out his career with team-highs of 22 points and 7 rebounds in a 76–69 Ducks loss to Mississippi State in the first round of the NCAA tournament.

[1][9][10] In his second season with the Spurs, Hairston was released in late July 2010 after the signing of Gary Neal and the subsequent log jam at the guard position.

[12] Despite being limited to only 16 games in his first season in the Lega Basket Serie A, a healthy Hairston would find good form for Montepaschi right before the start of the Final 16 Round Robin of the EuroLeague playoffs.

[26] On August 31, 2016, Hairston's contract was officially terminated by AEK, due to failing to pass the medical examinations before the 2016–17 campaign.

[28] After not playing for a season due to injury, on August 9, 2018, Hairston signed with the French club Fos Provence Basket.