Critical literacy—which I define briefly here as a lens that assumes no text is neutral and therefore an important goal of reading and writing is to evaluate and critique the power and perspectives that all texts contain—has been continuously well-theorized over the past half-century but is less frequently taught or studied in practice, especially in the United States. To help bridge this gap and to contribute to the conversation that identifies critical literacy as an invaluable approach to literacy education, this dissertation study is a qualitative multiple case study that investigated the teacher identities and pedagogies of five high school English Language Arts (ELA) teachers who self-identified as critical literacy educators. Using critical literacy theory to frame my understanding of teachers’ pedagogy and taking a sociocultural approach to understanding teacher identity, I sought to answer the following three questions: (1) How do critical literacy educators’ lived experiences inform their critical literacy teacher identities? (2) How do critical literacy educators’ identities inform their critical literacy pedagogy? and (3) What supports and/or challenges do critical literacy educators face when implementing critical literacy pedagogy, and how do they navigate challenges? To answer these questions I administered a survey to, collected teaching artifacts from, and conducted a series of in-depth interviews with each of my five participants. Analyses of these data indicated that participants’ critical literacy identities are largely the product of a variety of methods of self-selected professional development, and are deeply connected to social justice beliefs. To enact these identities and beliefs into practice, participants employed a number of student-centered classroom strategies to build students’ capacities to consider multiple perspectives and counternarrative stories, critique power in texts, and move towards taking social justice action. Finally, when enacting their critical literacy pedagogies, participants felt most supported by curricular freedom and self-selected professional development, and encountered the most challenges when it came to normative education elements that reflected dominant ideals such as suggested canonical texts and standardized testing requirements. The findings from this study have implications for critical literacy research, literacy teacher education, and K-12 schools, and include the importance of teaching critical literacy in theory and in practice across pre- and in-service teacher training, re-thinking the relationship between current standards and curriculum and critical literacy, and considering the value of curricular freedom in achieving critical literacy goals in K-12 classrooms.