Purpose: Marginalizing dynamics can emerge in school communities that are experiencing rapid demographic change, even when led by equity-oriented principals. The purpose of this article is to consider how educators can serve as transformative leaders through their performing cultural work that addresses inequity, crosses sociocultural boundaries, and fosters inclusion. Cornel West's theories on the cultural politics of difference inform the discussion, as does the literature on transformative leadership for social justice. Research Design and Methods: This comparative case study examined two North Carolina elementary schools that have experienced rapid demographic change, and it explored educators' and families' responses to cultural diversification and their views about school-family relations. Data analysis was conducted via an iterative process that identified common themes, entertained alternative conclusions, and triangulated interview, observational, and document data. Data revealed participants' general beliefs, concerns, and fears about demographic change, particularly as they relate to their communities' growing Spanish-speaking Latino population. Findings: Provided are data-based profiles of school principals and the sociocultural contexts of their school communities. Findings emphasize contradictions between the principals' equity-oriented stances and their exclusionary beliefs and practices; school community members' notions of cultural difference; and the biases, segregation, and brooding tensions affecting the schools. Implications for Research and Practice: The opportunities that principals have to perform cultural work as a form of transformative leadership are discussed, along with the value of explicitly infusing the notion of cultural work into transformative leadership frameworks. (Contains 2 notes.)