This chapter looks at the considerable challenges that Jim Zobrest faced as he attended Salpointe Catholic High School in Tucson, as the only deaf student in that elite institution. Jim’s experiment in mainstreaming did not succeed in overcoming his social isolation within the high school. The school itself largely left Jim to his own devices to succeed in this hearing environment. Jim therefore relied heavily on his interpreter, Jim Santeford, and his younger brother, Sam, to facilitate conversation with his teachers, classmates, and coaches. The kinds, methodologies, and technologies of deaf communication are also considered. Despite mostly succeeding in the classroom, Jim grew increasingly alienated from the school he and his family chose because he was unable to start on his school’s championship-caliber basketball team.