The purpose of this article is to explore a broad spectrum of some of the more prominent and interesting contract clauses that have worked their way into the practice of law in the business of sport. Many of the examples utilized in this article reflect the fundamental principles of contract law generally. The article explores contract clauses (and in some cases terminations) related to prominent coaches including Jim O'Brien, Kelvin Sampson, Tom Crean and Bruce Pearl. Other clauses explored include baseball's now outdated reserve clause, termination for cause clauses, morals, force majeure, liquidated damages, hazardous activity, best efforts, best interests of baseball, loyalty, no-trade, and other clauses as well. This article is also designed to offer the law professor pedagogical insights and queries when appropriate. Analyzing contract clauses in sports requires an understanding and appreciation of the interrelationship between judicial decisions among different jurisdictions, the evolving role of professional league commissioners, and the impact and history of law in general in the United States. This study and analysis of contract clauses also provides an opportunity to study American history, explore the infiltration of unions into major league sports, the changing view of civil rights in the 1960s, and especially the impact and influence of Curt Flood's challenge to the reserve system which made it all the way to the Supreme Court.