In light of increasing emphasis on the importance of post-secondary education to personal economic security, there is growing interest to promote college readiness initiatives in high schools, particularly for low-income and minority students for whom the harmful effects of institutional inequities on college readiness is well-documented. Relatively unexplored is whether and how deficit beliefs about these students influence college readiness initiatives. Extant literature establishes that principals play an important role in mediating organizational change and culture. However, there is scant research evaluating how principals' beliefs may influence their leadership towards reforming college readiness, particularly in regard to creating a college-going culture. This case study provides a critical examination of one principal who engaged in school-wide organizational change to create a college-going culture at an urban U.S. high school serving a high number of low-income and minority students. Discourse analysis revealed that although this principal's reform efforts were exemplary in many ways, he expressed deficit views of underrepresented students. Findings suggest that reductionist views of minority and low-income students conflict with initiatives to promote equitable college readiness. This case study uncovers a discursive dichotomy significant to examining the intersectionality of principals' beliefs and college readiness initiatives.