Born in San Diego, Barrett played two seasons of college soccer at UCLA and led the team in assists his second year.

Not known for a great first touch, his industrious play resulted in eighteen league goals in his time in Chicago where the often more heralded Calen Carr failed to impress.

Barrett tallied the game-winning goal in the ninth minute,[2] while Fire goalkeeper Jon Busch recorded eight saves in his second shutout of the season.

He, along with a first-round pick in the 2009 MLS SuperDraft and allocation money, was traded to Toronto FC on July 25, 2008, in exchange for the rights to Brian McBride.

[13] On March 8, 2014, in the Sounders season opener against Sporting KC, Barrett scored the game-winning goal in stoppage time with the game ending 1–0.

He made his debut for the United States men's national soccer team on June 22, 2008, coming on as a second-half substitute in a World Cup qualifier against Barbados.

Whilst recovering from injury Barrett and teammate David Horst would do live radio shows entitled 'the horse, the bear and the lion' which would be streamed on the RSL Facebook page.