This study explored how two mathematics/science subject-matter experts (Fellows) conceptualized urban classrooms and the students they worked with for a year, how they negotiated academic achievement with cultural and sociopolitical competence, and how their identities as educators were co-constructed and enacted. Using grounded theory, Fellows' weekly journals were analyzed using Ladson-Billing's three tenets of culturally relevant pedagogy. The Fellows' journeys point to the formation and presence of a prevalent tenet in their identities as urban educators, to the difficulty of integrating all three tenets, and to the tensions that educators experience as they try to become sociopolitically critical. (Contains 2 notes and 4 figures.)