Iowa State Hall of Famer Bill Cain dominated the Big Eight’s hardcourt in the late 1960s but took up his own form of protest in October 1968. The New York-born student-athlete and, thereafter, author of ISD’s “Cain’s Scrutiny” column moved to France after graduation (and being drafted by the NBA), where he found that race relations were different. The move was less a political statement than to feed Cain’s desire to see the world and play basketball. But in the process, Cain matured from a budding athlete advocate into an athlete ambassador. This chapter traces Cain’s transformation from an athlete advocate into an athlete ambassador. It examines an often overlooked form of athlete protest and how this background served Cain abroad, while highlighting the importance of the African American expatriate athlete. Importantly, this chapter investigates the linkages between sports protest and sports diplomacy through Cain’s experience as a de facto ambassador as he communicated, represented, and negotiated through basketball.