In this paper we weave lived experiences, those of a bilingual social studies teacher at a middle school in a large city in the Southwestern US, with critical theory/pedagogy and bilingual education. The purpose of this paper is to present an articulation of the practice of critical pedagogy in a bilingual educational context principally under the constraints of the No Child Left Behind Act of 2001 and its counterpart Race to the Top. We seek to share a few approaches that Matt, a bilingual social studies teacher, initiated to mitigate the effects of an oppressive but official curriculum and to encourage and foster the development of critical bi-literacy among his students.