In this article, the author discusses the complex challenges of high-achieving Black students who are successful in becoming immersed in predominately White STEM (science, technology, engineering, and mathematics) spaces and how such immersion can exacerbate their experiences of racial stereotyping and other forms of racial bias. The author illustrates these complex racialized experiences through the story of Maurice, a high-achieving high school mathematics student who successfully negotiated the White spaces he occupied yet did not indicate interest in pursuing a STEM-related career. Although Maurice developed sophisticated bicultural competencies that allowed STEM professionals and educators to view him positively, he decided that compromising his own racial, cultural, and individual identities to pursue a STEM college major and career was too costly. The discussion in general highlights how racial and ethnic stereotyping which is endemic throughout STEM education and careers can push mathematically competent Black students out of the STEM pipeline prematurely.