James signed with Toronto FC II on March 24, 2016.
In 2016 he began preseason with the first team where he appeared in five matches. He joined Toronto FC II for the remainder of their preseason and made four appearances. He was selected in the fourth round, 80th overall by Toronto FC in the 2016 MLS SuperDraft.
James joins the Young Reds after he split time between the University of Virginia and Pennsylvania State University (Penn State). During his time with the Cavaliers, he appeared in 35 matches, registering four goals and two assists. In 2014, he transferred to Penn State and appeared in 38 matches, registering four goals and 10 assists with the Nittany Lions over the past two seasons.