In the treatise That Every Good Person is Free, Philo compiles an extensive and diverse list of individuals as exempla in support of the thesis that the virtuous person is free even if enslaved. Among these, he includes the tragic heroine Polyxena who, in Euripides’ Hecuba, dies willingly rather than go into slavery. For Philo, this female tragic death functions as an a fortiori demonstration that all the more unassailable must be the freedom of the masculine subject. This mode of argument relates to Philo’s so-called “gender gradient,” whereby he depicts advancement in virtue as a move from the feminine to the masculine. This presentation employs Philo’s appropriation of the exemplum of Polyxena as a means of interrogating his gendered construction of virtue. On the one hand, Philo’s reading of Euripides anticipates the thesis of Nicole Loraux’s Tragic Ways of Killing a Woman (org. 1985) that suicide on stage blurs the distinction between masculine and feminine by moving the agency of women beyond its conventional limitations and passivity into the realm of male kleos. On the other hand, Philo’s argument participates in a wider interpretative tradition of this tragedy. Several other ancient authors—e.g., Pliny the Younger, Galen, Lucian, and Clement of Alexandria—also evoke the dramatic death of Polyxena. A survey of these literary appropriations reveals that Philo’s is not a unique application, but rather reflects conventional reading strategies. What emerges, then, is that Philo’s engagement with Greek literature proceeds from within an intellectual tradition that had pre-established moralizing applications of classical texts.