Most policy discussions around Latino boys aim to foster academic success without fully considering the way unequal outcomes are by design. The zero-sum nature of US education warrants a critical analysis and fundamental reimagining. I employ the lenses of critical social theory and critical discourse studies for a three-fold purpose: (1) examine the (im)possibilities of academic success, (2) examine how discourses of practicality are weaponized against efforts to enact structural change, and (3) engage the concept, imagining otherwise, in the field of education. Special attention is given to contemporary educational and political events to highlight the importance of going beyond “practicality,” abolishing all processes that generate unequal outcomes, and reimagining the forthcoming world of education. I call for a serious interrogation of educational structures, delving into a more critical and imaginative realm.