This qualitative research is a hermeneutic inquiry into learning about democracy through critical literacy in high school English language arts (ELA) education. The purpose of this study was to address the need for greater understanding of why critical literacy should be examined in high school ELA. The literature review connects historical theoretical and praxial implications for democratic practices. Critical literacy was explored through the hermeneutic method situated in one ELA teacher’s experience connected to a world view. Pivotal stages of critical literacy learning were explored in the classroom for transfer across education and democracy. Findings provide insight into the need for teachers to envision themselves as lifelong critical literacy practitioners and to engage in learning communities that explore the evolving needs of students. Essential philosophical underpinnings of the new philosophy of critical literacy education are explored; and suggestions for further professional development to increase subject knowledge are stressed. English language arts educators who wish to enact a critical literacy curriculum need to work together with students to engage in discourses around issues of power in literacy practices so classroom discourse may connect to the world.