A change is happening in the world of youth sports (Ripley, 2013; Longman, 2015; Fitzgerald 2013; Bowen & Hitt, 2013). Privatized youth sport teams, also known as club teams, have grown in number, size, and influence. Increasingly, high school age athletes are being forced to choose between their school team and their club team. While popular news outlets have reported on this change (Ripley, 2013; Fitzgerald, 2013), there has been no academic review of this particular phenomenon. The purpose of this phenomenological study was to compare the experiences of students participating in school-based and club-based athletics in order to better understand opportunities and potential disparities/inequalities between these two approaches to athletics. The identification-commitment model (Marsh & Kleitman) and the social inequality gap reduction model (Marsh & Kleitman, 2002) served as the lenses through which data was analyzed. Coaches, Parents, and Student-Athletes were individually interviewed or participated in focus groups. Three major findings emerged. First, winning and losing have taken on different meanings between high school and club teams. Second, athletes on both high school and club teams were able to develop a form of social capital (Coleman, 1987), however, only high school athletes saw an associated academic benefit. Finally, whereas high school athletes were able to participate with little monetary investment, the costs associated with club teams were very high and access to financial assistance was either not available or was not well-known. Implications of these findings and general recommendations as well as recommendations for parents, athletes, high school, and club officials are discussed.