James is a Pittsburgh native born in the city and raised in Western Pennsylvania. He graduated from South Hills Catholic High School (now Seton La Salle High School) before moving on to Villanova University (no relation). While a student at Villanova University, James was a member of the International Brotherhood of Teamsters, Local 926, as a factory worker, during the summer as well as having other labors and office jobs. Upon graduation from Villanova University, James was granted a full honors scholarship to the University of Pittsburgh, where he was a member of the Law Review. During his law school tenure, James was a railroad worker and was a member of the Brotherhood of Maintenance of Way of the Brotherhood of Teamsters, Local 1049. James was also chosen to work as a summer associate at Reed, Smith, Shaw and McClay, a large corporate firm.