Criminalizing the harms of the powerful has considerable appeal for those who desire a more tractable, ethical and sustainable business sector. Yet, attempts to both establish criminal offences and to enforce them once they are enacted often face perennial challenges. These challenges are a product of the ambiguities—economic, moral and legal—associated with the conduct sought to be criminalized, in this case cartels, and with the character of the criminal law itself. Following Aubert, we argue that exploring these ambiguities reveals critical social and economic shifts in society. Further, these shifts pose significant challenges to the legitimacy of incumbent governments. The paper makes these arguments drawing on the recent reform criminalizing cartel conduct in Australia, teasing apart the multiple ambiguities involved and, in particular, how they map the shift in the Australian Labor Party’s policies away from welfare providing security to citizens to an embrace of market competition.