This participatory qualitative inquiry explored the fluctuating subjectivities of, and advocacy performed, by three content area teachers in a high-immigrant population, urban high school in the New South. Using a neo-Vygotskian theoretical framework highlighting the socially constructed nature of teacher positionality (Holland, Lachicotte, Skinner, & Cain, 1998), I narrate the sometimes-conflicted understandings of three teachers' advocacy and the sense that it brought to their professional selves. Data analysis revealed the generative hesitations and complications that arose as the three teachers cast and recast themselves as successful. Findings highlighted the complexities of the enactment of "caring" and "never giving up" in an advanced Math III course; the self-reflective hesitations surrounding a Latin American Studies teacher's piloting of a social justice framework; and the incompleteness of a dual licensure ESL/ Social Studies teacher's efforts to make more of a difference in her newcomer immigrant students lives. Implications for research and praxis highlight the spectrum of advocacy in urban schools and its tensions.