Dorothy Day was a progressive and revolutionary activist who dedicated her life to combat issues of war, poverty, homelessness, and oppressive capitalist policies, yet she continuously stood by essentialist notions of gender and was critical of the gender politics of Emma Goldman, and many second wave feminist such as Betty Friedan. Therefore, this analysis provides an interpretation of the contradictions and contentious in Day’s narrative of her life, as well as her publicly expressed opinions in newspaper publications by engaging in a critical and theoretical analysis of Day’s subjective archives (i.e. her autobiography, newspaper publication, diary entries, etc…). As Day was embedded in a particular social context and structure, this research will aim to understand how these contentions provide insight into the gendered structure of Days life, which presented limitations that shaped her gendered experience, as well as opportunities that enabled her to challenge and shift the structure. This analysis will use Day’s subjective accounts to gain insight into the inequalities Day faced, how these inequalities shaped her, and how diverging aspects of her life's account serve as an interesting analytical field in understanding how inequalities are challenged on one hand, and reaffirmed on the other. To do so, this essay will borrow heavily from the theory of “gender as a social structure” (Risman) in order to interpret the gender structure in Days life, which includes individual, interactional, and macro levels. The purpose is not to create a factual biographical account of Day’s life and her gendered experiences, but to critically analyze and interpretively engage in her thinking and philosophies with a contemporary gender lens in order to interpret how Dorohy Day’s narrative account can serve to reveal how “structure shapes individual choice and social interaction but also how individuals and groups of individuals (e.g. social movements) can and do modify gender structures over time” (Risman, social, 30).