This chapter examines how gender dynamics shape violent acts among Mexican American young adult males with a history of adolescent gang membership. We use the concept of hegemonic masculinity to examine the various ways that gender is performed in acts of violence (Connell, 1995). Masculinity is not a fixed entity or individual personality traits, masculinities are “configurations of practice that are accomplished in social action and, therefore, can differ according to the gender relations in a particular setting” (Connell & Messerschmidt, 2005:836). In other words, “gender identity is never a completed project, but always a developmental process which unfolds within a social context” (Messner, 1990:209). Nevertheless, the tendencies for aggression and violence are central to what it means to be masculine (Messerschmidt, 2000; Crowley, Foley et al., 2008) because “real men” must show others that they are not afraid (Kimmel, 2010). We examine the unfolding of masculine identity among disadvantaged Mexican American men in two different yet related contexts: violent acts with other men and the retelling of these violent acts. Among disadvantaged men, in general, social class is central to masculinity because these men are likely to have limited options in accomplishing their masculinity compared to men with more advantages (Britton, 2011; Messerschmidt, 1993; Stretesky & Pogrebin, 2007). The type of masculinity expressed by Mexican American males, more specifically, varies depending on a constellation of variables related to social class including income, generational status, education, and association with the criminal justice system (Rios, 2011; Valdez, 2007).