Not all high school students go to college. Yet, because there is currently such a dominant emphasis on "college for all," preparing non-college-bound students for career-readiness has received short shrift. This issue is particularly important for English learners (ELs) because close to half of high school ELs do not advance to postsecondary education. Through a longitudinal ethnography of two underperforming, non-college-bound ELs, I examine how and why a relatively well-resourced school allowed these students to graduate without college- and career-readiness. I argue that although there were substantial structural inequalities that led to the under-education of the two ELs, educators at the school were largely unaware of such barriers and attributed the ELs' underachievement to the students' own deficits. I counter this institutional deficit orientation with alternative stories of student assets that illuminate the substantial strengths and talents that the focal ELs possessed, which, if recognized and integrated into their education, could have led to career-readiness.