Foreign-born athletes are an integral part of global sports competitions as naturalized citizens of other countries. The United States and Canada are the top two major players in this global phenomenon (CapRelo, 2018). The purpose of this study was to understand why athletes from these countries seek foreign citizenship through naturalization using Winter Olympic sports as a medium and what legal basis exists. World system theory guided this research investigation. Research questions include: a) Why are the USA and Canada the largest exporter of naturalized athletes to other countries and what differences exist in terms of policy and legal requirements that promote this global phenomenon? b) What explanations exist to explain the naturalization of athletes? Data collection involved utilization of secondary sources –Sports Reference LLC, official documents from the IOC and NOCs, and newspapers. Data analysis involved the use of thematic analysis. The findings reveal that the USA and Canada to lose the most athletes in the recent Winter Olympics to naturalization because IOC provides a legal basis and policy requirements for this happening. Explanations for naturalization center opportunities for Olympic participation, honoring parents’ heritages and helping underrepresented countries in the Winter Olympics.