African American males from urban communities have been attending Jesuit high schools in urban spaces for many years, yet little to no literature exists that explores their experiences while attending these elite private schools. This qualitative study of 10 African American males from an urban community attending a similarly positioned Jesuit high school on the East Coast revealed their struggles with both inter- and intra-racial dimensions of their experiences. This paper explores their challenges with racist comments within the interracial context and their understandings of "acting White" within the intra-racial context.