James played college soccer for the University of Connecticut, and was a 2007 Hermann Trophy candidate and Lowe's Senior CLASS Award finalist.

James drafted 9th overall in the 2008 MLS SuperDraft by Toronto FC, and played with them during their 2008 preseason, but suffered a shoulder injury against the New York Red Bulls[1] and missed his side's first two matches of the 2008 regular season.

James was traded to Houston Dynamo on 12 December 2008 as part of the deal that took Dwayne De Rosario to Toronto FC.

On 14 August 2009, after a short loan period at Minnesota Thunder in the USL First Division, James was traded to D.C. United in exchange for a third-round pick in the 2012 MLS SuperDraft.

[4] He made his debut on the next day as a second-half substitute in the second leg of the Crew's CONCACAF Champions League quarter-final series against Real Salt Lake.