This article explores how incarcerated youth and adult supervisors contest claims to identity via language of "representing". Comparing how youth and adults "represent" in discussions of their own past and future selves sheds light on the constrained universe of discourse within which both groups work to express identities and on the basis of which we counsel, mentor, and educate young people. Acknowledging these constraints can contribute to understanding what I call "exceptionalism"--the idea that only exceptional poor and raced young men, through great personal effort and sacrifice, may resist the lure of the "street". I conclude by discussing implications of this work for education and youth development work both inside and beyond the juvenile justice system as well as for research across lines of difference by committed "outsiders".