In this article, I advocate the need to carry out broader socio-cultural contextual analyses and more systematic psychological analyses of individuals sporting behavior. Here, I offer a multi-level contextual approach as a potentially fruitful strategy for investigating the dynamic interplay of individual and contextual factors in traditional and new, or "alternative," sports. To highlight the potential of this approach, I apply it to an incident that involved American snowboarder Lindsey Jacobellis at the 2006 Winter Olympics. Here, I draw upon a multi-methodological approach to analyze her experiences on multiple contextual levels-micro, meso, and macro. In so doing, I link her behavior with the larger social, cultural, and political structures in which it was produced. Ultimately, this article illustrates that in-depth knowledge of sporting cultures and their development and the values of cultural members is an essential prerequisite for those hoping to understand and explain the behaviors of athletes and practitioners in alternative sports such as snowboarding.