This case study presents students with a contemporary issue within higher education: the use of athletics to positively affect an institution’s prestige. Dwight Stanley, an athletics director at Fairfield Tech College (FTC), is tasked with determining if his institution should maintain its membership in the NJCAA or pursue membership in another association, namely the NAIA or NCAA DIII. This case study is designed to encapsulate the tension sport managers face as they encounter complex decisions. Accordingly, each membership option is presented with its advantages and disadvantages, as well as its supporters and detractors. Consequently, students are required to critically asses a variety of factors to determine FTC’s most feasible undertaking. As many students aspire to become intercollegiate athletic administrators, this case study provides an excellent way to engage students in considering the complexities of such positions. Additionally, though the case study is presented within the context of intercollegiate athletics, the analytical process required to select a course of action is transferable to other segments of the sport industry. This case study is applicable to several different areas of undergraduate and graduate study in the sport management field, including athletics administration, strategic management, and policy and governance courses.