How do gender stereotypes shape the media portrayal of women executives? Because both the executive position and the management of large-scale crime are coded as masculine, women are often perceived as outsiders in these domains, making their portrayal particularly susceptible to stereotyping. Drawing on Role Congruity Theory, I analyze media coverage of executives in Mexico and Peru using a content analysis of 104 newspapers. I find that gendered stereotypes are primarily used as political critiques. Feminine-coded traits are most frequently used as negative evaluations across both male and female executives. Comparing portrayal of Castillo and Boluarte with AMLO and Sheinbaum, I find that feminine traits are more likely to be portrayed positively during periods of high executive approval and more negatively when approval declines. Overall, the findings suggest that role congruity operates less through fixed gender identities and more through the evaluative coding of stereotypical traits in response to political performance.