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This paper presents findings from a multicase study exploring the advocacy work of four effective teachers working in high-need schools. Not only did the teachers foster immediate and future success for their students through anticipatory advocacy, that is intervening actions teachers take that result from a dual awareness of students’ immediate and future needs, but also they benefited professionally and personally as their beliefs about and commitments to their schools and students were confirmed and strengthened, allowing them to sustain their visions for their work and to resist professional weathering forces. This paper focuses on the ways the teachers used ambitious teaching practices to advocate for their students’ futures as intellectual people with “agency in the world.”