In this article, the author’s intent is to begin a conversation centered on the question: How might mathematics educators ensure that gatekeeping mathematics becomes an inclusive instrument for empowerment rather than an exclusive instrument for stratification? In the first part of the discussion, the author provides a historical perspective of the concept of “gatekeeper” in mathematics education. After substantiating mathematics as a gatekeeper, the author proceeds to provide a definition of empowering mathematics within a Freirian frame, and describes three theoretical perspectives of mathematics education that aim toward empowering all children with a key to the gate: the situated perspective, the culturally relevant perspective, and the critical perspective. Last, within a Foucauldian frame, the author concludes the article by asking the reader to think differently.