A draft pick out of William and Mary, Barrett helped San Jose to their first MLS Cup championship in 2001 and their first Supporters’ Shield in 2005. After starting his career in midfield, Barrett moved to left back in 2001 and had two standout seasons for the Quakes in 2001 and 2002, earning an MLS Best XI nod in 2002. After spending two years in Denmark, he returned in 2005 and the Quakes, with Barrett as team captain, put together of the best seasons in MLS history with an 18-4-10 record that included a 14-game unbeaten streak to end the season.