In recent years mentorship has become a popular 'solution' for struggling boys of color and has led to the recruitment of more male of color teachers. While not arguing against the merits of mentorship, this article critiques what the author deems 'corrective representations.' Corrective representations are the imagined embodiment of proper and productive masculinities that male of color educators are asked to perform. This discourse perpetuates confining representations of identity and locates the problem of boys of color within their own actions. Designed as an ethnographic case study, this article explores the life of one Latino male teacher as he navigates discourses of corrective representation as coordinator of his school's Latino boys program. This project provides a detailed account of the cultural politics of Latino male mentorship and offers the notion of a critical borderlands approach to identity as an avenue to problematize essentialist and deficit approaches to Latino boys.