This dissertation critically examines how socioeconomically advantaged, white progressive parents talk about what schools they choose for their children in ways that maintain, challenge, and disrupt inequity and white supremacy within the K12 education system. I ask: how do white, socioeconomically advantaged, politically progressive parents construct their white racial identity in relation to power, privilege, and racial difference through their K12 school choice discourse? I demonstrate how parents constructed their white racial identities in a range of ways that reflect varying stages of critical awareness of their privileged positionality. I account for this variation through considering how parents differently emphasized the competing values of community and the individual in their school choice discourse. Despite exhibiting significant differences in their varied stages of critical awareness, I argue progressive white parents must contend with the dynamics of the inescapability of the tension between reconciling their broader concerns for their communities with their narrow focus on securing individual advantages. Engaging qualitative field methods, I conducted interviews and focus groups with forty-three white, politically progressive, socioeconomically advantaged parents of K12 school-aged children living in the Madison, WI area. Each dissertation chapter engages with these transcripts to pursue separate but related questions focused on four key concepts: choice, ideology, identity, and difference. This project intersects critical whiteness studies with the rhetoric of education policy to contribute to rhetorical scholarship that deepens our understanding of the tensions of white political progressives through attending to their privileged position in relation to systems of inequity in the K12 education system.