In the first interview session, conducted on May 16, 2012, Gillette discusses his early life in Milton-Freewater, Oregon, including his education and family life. He describes a childhood trip to Washington, D.C., which inspired him to pursue a career in public service. He talks about his college experiences at Whitman College in Walla Walla, Washington, including his marriage to Judy Saima Cox and becoming a parent while studying. He speaks at length about his experiences studying law at Harvard University.