Does grounding in the philosophical dimensions of teaching, learning, and education systems contribute in meaningful ways to being a good teacher? This chapter will answer “Yes” to that question and assert that, indeed, philosophical dimensions contribute in meaningful ways, though they are being squeezed out for contributions that are more easily quantifiable and measurable. Habermas’s knowledge constitutive interests (KCI)—technical, practical, and emancipatory—can help describe and dissect this problem and provide a path forward. In particular, the KCI constructs can serve as a critique of the ideology of positivist technocratic forms of schooling wherein the emancipatory interest manifests through philosophical critique in education as a bulwark against intellectual and social reproduction. I will show that a teacher education focused on technical and practical interests will serve only a technocratic form of teaching that ignores and reifies oppression. This perspective on teaching recommends the construction of the teacher as not only a professional skills expert, but as a political and social being embedded in a community, a person with rights and desires that extend beyond his or her employment, and one with obligations to educate students about the world and their agency in it. This requires engaging philosophical critique in the making of a teacher, a teacher who can then engage students in a similar exercise. To omit the philosophical dimensions of life, let alone teaching, is not only a failure of professional preparation, but a repudiation of educational imperatives.