Psychopathy has attracted copious attention in research. Initial theories were developed primarily on case studies of men (Cleckley, 1976). Yet, due to lower scores and misrepresentative correlates, there is reason to believe psychopathy does not paint an identical picture across the genders. Data have shown a BPD diagnosis may act as a female-specific indicator of antisocial tendencies (Blonigen et al., 2012). However, what we have come to understand about these two constructs in terms of their emotional comprehension underscores a unique contradiction: those with BPD have a hypersensitivity to negative emotion, while those with psychopathy possess a deficit to similarly connoted feelings. A primary aim of the present study is to delineate the clinical presentation of psychopathy in incarcerated women as it intersects with borderline personality disorder and alexithymia. Mediation analyses with bootstrapping were conducted to test the primary hypothesis. BPD fully mediated the relationship between psychopathy and alexithymia in our sample (p < 0.001). Further exploratory analyses delineate this relationship in terms of TAS subfactors. Interesting implications exist for how psychopathy and BPD diverge in terms of their emotional literacy. Continued research is critical; it will not only help to understand these mechanisms, but also to inform tailored treatment that is less costly, more eective, and deterrent of negative psychopathic behavior.