This research addresses the challenges of engaging students in critical conversations about controversial topics in racially homogeneous settings. Data analysis from this qualitative, phenomenological study reveals how veteran high school teachers understand and experience their contexts and how they navigate the complex instructional strategies required by English language arts state learning standards yet may be challenged by community stakeholders. Findings suggest that teachers enjoy differing levels of freedom regarding content yet focus on building relationships and engaging students' thinking. This study offers a framework for critically engaging students while attending to distributive and relational aspects of justice-oriented teaching.