In 2011, the Québec government launched the Charbonneau Commission, a monumental public inquiry tasked with getting to the bottom of a major collusion and corruption scandal involving elected officials, municipal employees, and construction industry contractors. The scandal concerned the awarding of municipal contracts that led to a significant waste of public funds. Yet, at the time, all municipal sector organizations involved were regulated by several controls, particularly in the granting of public contracts. How could the situation deteriorate to the point where collusion became the “usual” way of managing public contracts, particularly in the City of Montréal? The objective of this article is to better understand how deviance became the “norm,” such that the social actors involved came to adopt a deviant identity rather than obeying socially accepted rules. Conceptually inspired by the work of Becker (1963), Foucault (1977), and Giddens (1991), this article is based on the in-depth testimonies of two key actors in the collusion scheme. Our aim is to better understand the process leading to the adoption of deviant behavior and the often illusory character of organizational and regulatory controls.