This thesis identifies the variance in gender empowerment between Argentina and Chile, two countries that share countless parallels in histories, cultural norms, and political achievements. Using women’s formal legislative representation as a gauge for gender empowerment, this comparative study uses a most-similar-systems design to investigate and generate a hypothesis of the factors that contribute to Chilean women’s lack of empowerment, contrasting with the mechanisms by which Argentine women have achieved empowerment. Both Catholic nations of the Southern Cone re-democratized following military regimes, currently enjoy female heads of state and possess similar cultural phenomena where motherhood has defined women’s social and political roles for decades. Nevertheless, Argentina and Chile remain starkly dissimilar in the scope of women’s legislative presence. Chile’s open-list electoral system that exposes women to rampant machísmo and the conservative influence from the Church that encourages women to embrace their primary role as mothers are two significant factors that prevent women’s legislative representation and thereby empowerment. Contrarily, Argentina possesses one of the leading levels of gender empowerment in the world. At first glance, one may attribute the variance to the Ley de Cupos, the quota law requiring parties to enlist a critical mass of women candidates. While the Ley is certainly necessary to promote gender equity, it remains insufficient. The historical precedence of women in politics as well as an electoral system conducive to the quota’s progression allow Argentine women to achieve a greater level of political empowerment than do women in Chile, further evidenced by the Argentine success over similar laws in other Latin American countries.