James left juvenile hall, and inspired by civil rights attorneys William Kunstler and Morris Dees, left for Antioch College at age 17 to study pre-law. During a break in his first semester, he was involved in a gang fight and beaten in the back of the head with a baseball bat, which left him with left hemispheric brain damage. He was not able to speak or move the right side of his body. After intensive physical and speech therapy, he eventually recovered his speech and motor skills, but he ended up homeless, living on the streets and in squats across the country. He eventually settled in Boston, Massachusetts.