Given educators' call to equalize educational opportunities, research is needed to illuminate promises and tensions in schools that resist negative labeling and sorting of nondominant youth. This article examines an urban high school that challenges traditional expectations for low-income, Latina/o students by engaging in "relabeling," a process whereby school staff socialize students, who have been viewed historically as not "college material," to see themselves as collegebound professionals. The authors use this school as a critical case study to highlight the importance of challenging negative messages about Latina/o youth and affirming students' potential, inculcating behaviors associated with academic and professional success, and marshaling multicultural capital to prepare students to navigate between the worlds of college and home. Authors also describe the tensions in balancing dominant and nondominant cultures, comportment and academics, and "ganas" (determination) and high standards. These findings contribute to deepening relabeling theory in three critical domains: rethinking Bourdieu's cultural capital theory, developing academic college-level skills, and affirming multicultural capital.