In the United States, women have long held the right to vote and can participate fully in the political process, and yet they are underrepresented at all levels of elected office. Worldwide, men’s dominance in the realm of politics has also been the norm. To date, scholars have focused on supply-side and demand-side explanations of women’s underrepresentation but differences in how men and women assess electoral risk (the risk involved in seeking political office) are not fully explained. To fill this gap, I explore how evolutionary theory offers insights into gendered differences in political ambition and the evaluation of electoral risk. Using the framework of life-history theory, I hypothesize that both cognitive and environmental factors in human evolution, particularly as they relate to sexual selection and social roles, have shaped the psychology of ambition in gendered ways affecting contemporary politics. Cognitive risk-assessment mechanisms evolving in the hominid line came to be expressed differently in females and males, in women and men. These gendered expressions plausibly reflect differentiable environmental pressures in the past and may help explain behaviors in and barriers to women’s electoral political activity in the present. If so, then the success of efforts to increase such activity — or, regressively, to suppress it — may be better understood.