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Political executives often adhere to informal traditions established by their predecessors. Without the backing of formal laws, elites have incentives to violate norms, particularly if doing so yields an electoral advantage. When do constraining executive norms carry weight, and when do they falter? We examine an infinitely repeated principal-agent model to analyze two mechanisms for maintaining executive norms: intra-party accountability between an executive and their political party, and inter-party competition. We also consider the role that executive popularity, differential time horizons, and crises play in norm violations. We uncover the equilibrium costs associated with the unraveling of executive norms in terms of increased selection of low quality executives and greater variance in policy quality. In an extension, we explore how these factors may lead to the legal formalization of the norm. The insights from the model are used to categorize types of executive norms and their relative fragility. In addition, we examine in detail the life-cycle of the ``two-term tradition'' of the American presidency. Overall, the study holds implications for how informal institutions regulate executive behavior and for understanding the interplay between informal and formal institutions.