Specialized teacher preparation programs are graduating teachers with commitments to advocacy. This expanded definition of teaching stands in opposition to traditional expectations for the role of teachers that have developed during the history of U.S. education into organizational and social frames that reinforce tradition and work against reform. These influences constitute forces of professional weathering that may wear down teachers’ visions and actions for their work. This multicase study focused on four graduates from an intensive two-year teacher preparation program that included initial certification along with induction support in the second year of the program as they completed master’s degree requirements. The inquiry sought to understand how they envisioned their roles as teacher advocates and how they enacted and sustained their visions, resisting traditional teacher roles. Participants were graduates of the same cohort of the preparation program who were completing their second year of teaching in urban high-need schools and who had been nominated and confirmed as effective teachers of diverse students by faculty members of the university program and of local schools. Program materials were analyzed as background material to establish context. Primary data that were inductively and iteratively analyzed included extant course assignments, three individual interviews with each participant, three school-related observations, and three focus group interviews. Findings provide insight into the ways in which the teachers enacted a vision of anticipatory advocacy. Anticpatory advocacy includes intervening actions that are the result of a dual awareness of students’ immediate and future needs and have implications beyond boundaries of time and space in an effort to positively influence students’ lives in the immediate as well as distant future. The teachers, each of whom held beliefs that aligned with the culturally relevant foundations of the program prior to their selection, employed tools related to responsive classroom management, ambitious teaching strategies, and professional collaboration that they acquired and honed during their program. By working backward from the classrooms of effective teachers, the study links classroom practices with teacher preparation, providing direction for stakeholders concerned with the development and retention of high quality teachers for all children, especially in challenging school contexts.