Exacerbating the risk of “malign policy,” the soaring diffusion of the revolving door phenomenon has prompted regulatory intervention. Focusing on executive branches in charge of issuing and managing government debt—debt management units (DMUs)—this article delivers a case study assessing the effectiveness of revolving door restrictions. It does this by evaluating oversight and enforcement quality. In government debt management, the revolving door is the horizontal flow of public officials to dealer banks, and vice versa. Drawing on a comparative legal analysis across eight OECD countries and career data from a unique sample of public debt managers, this study provides empirical evidence of potential and actual breaches of regulations in force. Highlighting how career moves are potentially intertwined with cases of disruption of public resources, this study aims to steer regulators in the effective management of the risks posed by the revolving door phenomenon.