Before playing at Williams, he was a star of his prep school soccer team at Choate Rosemary Hall in Connecticut.

He did not make the Fire team, however, and was traded to Kansas City Wizards for a third-round 2005 MLS SuperDraft pick.

In August 2008, Khari then moved to Aalesunds FK in Norway, where he was joined by Jamaican international teammate Demar Phillips in the midfield.

Stephenson returned to the United States on loan from Aalesunds FK and signed with the San Jose Earthquakes of Major League Soccer on 9 August 2010 until the remainder of the MLS season.

[7] Stephenson appeared for the Jamaican U-20's in the 2001 FIFA World Youth Championship in Argentina and made his debut for the 'Reggae Boyz' in 2004 against Guatemala.