Sport is filled with much paradox. Sport, by nature, is inherently based on athleticism, fitness, strength, and other seemingly healthful benefits. Though such benefits are common, there is the constant presence where the unhealthy and inappropriate associations exist. This dichotomy is quite prevalent in many forms in contemporary sport. Among the most troubling occurrence with contemporary sport is the increasingly visible prevalence of criminal behaviors associated with sport. This text seeks to examine some of the most relevant and thought provoking occurrence of criminal and quasi-criminal behavior in sport. Through identifying pertinent issues, including motives and causes associated with such actions, this work aims to present a comprehensive view at these issues while providing regarding ways such matters can be effectively dealt with in contemporary society. Among the topics to be addressed in this work include: drug issues, violence, gambling, ticket scalping, hazing, fraud in nonprofit sport, homeland security issues and disaster preparedness in sport, intellectual property (trademark law, copyright misappropriation, and criminal implications), and beyond.