Case law discussions in sport management scholarship and pedagogy frequently focus exclusively on one primary topic area. Thus, a case serves as a textbook example of a specific legal theory and management practice points. Occasionally, a multi-faceted case allows for an elaborate, comprehensive analysis, integrating teaching concepts from several areas of the law. Such is the factual scenario of O’Brien v. Ohio State University. This teaching case study offers lessons in Contract Law, NCAA Compliance, and International Arbitration. The complex web of these three intersections of sport law, policy, and management provides students and scholars the opportunity to both delve deeper into concepts and learn crucial details in a broader context. Key facets of each portion instrumentally affected the other portions of the case, triggering chain reactions. Teaching this case contributes to students’ appreciation of these intertwining concepts, and creates overall awareness of potentially far-reaching ramifications for each action.