Over the last two decades, a growing body of scholarship has examined how whiteness is socially constructed as “objective” and “neutral” in the US and elsewhere. This article seeks to trouble such a position for white teachers in the multiracial classroom, particularly those that focus on multiethnic literatures. Drawing upon scholarship in critical whiteness studies, personal experiences with students, and reflections on multicultural literature, this article advances an educational philosophy of investment wherein privilege and subjectivity are made legible in the learning process. In this model, educators and students work toward the discomfort that often comes from recognizing the risks and rewards of acknowledging one’s positioning within a racial order.