Despite persistent class and race inequalities in educational attainment and achievement in the U.S., hegemonic cultural ideologies and urban education politics and policies continue to proceed from an insistence that education is the great equalizer. These ideologies do not take into account the ways that normative school culture and pedagogical praxes take for granted middle-class, white-supremacist cultural assumptions that privilege student populations whose social locations already probabilize high rates of achievement and attainment. Vast research published in The Urban Review and elsewhere has demonstrated the importance and efficacy of culturally sustaining pedagogy for improving outcomes for economically marginalized students of color (Allen in Urban Rev 47(1):209–231, 2015; Delpit in Harv Educ Rev 56(4):379–386, 1995; Farinde-Wu et al. in Urban Rev 49(2):279–299, 2017; Gay in culturally responsive teaching: theory, research, and practice, Teachers College Press, New York, 2010; Graves in Berkeley Rev Educ 5(1):5–32, 2014; Jemal in Urban Rev 49(4):602–626, 2017; Ladson-Billings in Crossing over to Canaan: the journey of new teachers in classrooms, Jossey-Bass, San Francisco, 2001, The dreamkeepers: successful teachers of African American children, Jossey-Bass Publishers, San Francisco, 2009; Lee in Culture, literacy and learning: taking bloom in the midst of the whirlwind, Teachers College Press, New York, 2006; Marciano in Urban Rev 49(1):169–187, 2016; Nieto in Language, culture, and teaching: critical perspectives, Routledge, New York, 2010; Paris in Educ Res 41(3):93–97, 2012; Paris and Alim in Culturally sustaining pedagogies: teaching and learning for justice in a changing world, Teachers College Press, New York, 2017; Wiggan and Watson in Urban Rev 48(5):766–798, 2016; Yosso in Race Ethn Edu, 8(1):69–91, 2005). This article uses rich ethnographic data from a transfer school in Brooklyn, New York that serves financially insecure youth of color who are “over-age and under-credited.” These data and my analysis showcase the expertise and indigenous knowledges of teachers who practice cultural relevance and critical racial awareness in order to engage, retain, graduate and prepare students who are historically and presently marked for failure by an education system that has always been more adept at reproducing social inequality than disrupting it (Borck in Qual Inq 20(10):1–8, 2016).