Most research finds that individuals are drawn to the correctional officer occupation for the pay and benefits or because it provides a new and exciting opportunity. However, these are not the only interests for choosing a correctional officer position. The current study draws on a sample of pre-service correctional officers surveyed prior to beginning their jobs (N = 673). In the spirit of the deviant case method, we focus on a subset of our sample who provided problematic motivations for becoming officers (n = 38). Using a thematic analytic approach, we identified five broad themes within this nefariously/disconcertingly motivated sample: use of force, punitive focus, power and control, cavalier ulterior motives, and problematic social boundaries. We theorize, based on prior research, that these individuals could constitute a meaningful minority that may contribute to the detriment of both their organizations and those they are overseeing. Future research should explore this possibility.