He does commentary for San Jose Earthquakes games on Comcast Sports Net Bay Area Gray played forward and midfielder at the University of Portland from 1999 to 2001.

He scored a total of 32 goals and 12 assists in his three years for the Pilots and was voted a second-team All-American and first-team All-WCC as a junior.

Gray's versatility may have been a hindrance to his development, however, as even three years into his career with the Fire, it is unclear what his position should be; although a consistent starter, he was longing to play in his hometown.

Gray was traded to San Jose Earthquakes in June 2005 in exchange for a second-round pick in the 2006 MLS SuperDraft.

In June 2007, Gray was traded with a second-round pick in the 2008 MLS SuperDraft to Los Angeles Galaxy in exchange for Nate Jaqua.