This article intends to support the efforts of administrators, teachers, and community activists to center race, equity, and anti-deficit perspectives within the practice of school leadership. By drawing upon methods of critical race studies, and Du Bois's 1935 concept of the sympathetic touch, the author provides examples of anti-deficit approaches to sympathetic leadership in a large, diverse high school in California. Through reflections and recollections upon this case study, the author underscores ways for school leaders to formulate the conditions for college-going expectations for low-income immigrant students. This retrospective account includes concrete leadership examples, political strategies, and scenarios to illuminate the relevance and utilities of the sympathetic touch in educational leadership. In effect, the article calls for school leaders to harness anti-deficit and anti-oppressive mindsets in the work of inclusion, equity, and social justice.