This article presents a philosophical and pragmatic critique of critical mathematics (CM) and current vocational mathematics (VM) in the United States. I argue that, despite differences, CM and VM advocates share the view that the inauthentic contextualization of secondary mathematics does particular harm to students from historically marginalized groups and that the subject therefore should be recontextualized to address their lived experiences and apparent futures. Drawing on sociological theory, I argue that, in being responsive to so-called authentic real-world concerns, CM and VM fail to be responsive to the self-referential principles and specialized discourses necessary for future study of mathematics and, as such, may further disempower the very students that CM and VM advocates seek to empower.