This episode offers a comprehensive look at the foundations and complexities of contract law, analyzing its underlying philosophical tensions, practical applications, and theoretical justifications. Key excerpts explore the historical tension between individual freedom and social control within contract law, examining the shift from the classical emphasis on private autonomy to modern doctrines that incorporate greater social regulation, such as in cases involving unconscionability or inequality of bargaining power. Several sections analyze the theoretical bases for enforcing contracts, contrasting the sanctity of promises theory with the will theory, the injurious-reliance theory, and the equivalent theory, all of which seek to justify contractual obligation. Finally, the sources introduce sophisticated thinking tools for legal analysis, specifically using Wesley Hohfeld's framework to clarify legal relationships (right, privilege, power, and immunity) and the concept of acoustic separation to understand how conduct rules for the public may differ from decision rules used by judges.