Ivan (pseudonym), the son of Mexican migrant farmworkers, rarely spent more than six months in the same school and by high school was still classified as an English language learner. This article traces Ivan’s experiences as a language learner and writer, telling his story in his own words through his writing and ethnographic data collected during his junior year of high school and his first year of college. I examine how literacy sponsors (Brandt, 2001) helped or impeded his reading and writing as he worked to change his life. Through Ivan’s writing and oral reflections, I argue that rather than solely supporting their reading and writing development, literacy sponsors for immigrant second language writers support learners as a whole. Central to Ivan’s evaluation of his literacy sponsors is the role of caring relationships—or lack thereof—that endured longer than the technical literacy skills he learned from any one sponsor.