In Puerto Rico, the issue of gendered violence has been bubbling under the surface for decades from a centuries-old paternalist culture. Examining culture through literature, my dissertation illuminates the entangled connection between colonialism and gendered violence as my analysis traces in literary texts from the late nineteenth century to the 1970s and early 1980s a collective sense of disillusion, defeat, and demoralization that stems from Puerto Rico’s perpetual colonialism and establishes what I call a foundational pessimism. I argue that colonial and gendered violence are inextricably linked and manifest as a web of pain where it is impossible to closely examine one without confronting the other. Furthermore, I suggest that these forms of violence leave wounds that are inherited through generations provoking a haunting effect within families and society at large. Starting in the first chapter with a reading of La charca (1894) by Manuel Zeno Gandía in light of Anne McClintock’s notion of the gendered nation and following up with two of René Marqués’s plays, La carreta (1953) and Los soles truncos (1958), I demonstrate the various reactions to colonialism that led to a paternalist nation that dismisses women. In my readings of these texts, all penned by men, I argue, moreover that Gandía’s canonical national novel set the stage for subsequent canonical literature in the early twentieth century to perpetuate harmful and sexist stereotypes about women. In the following two chapters, my analysis pivots to feminist fiction by women writers that brings these issues to light. In my reading of Rosario Ferré’s “Amalia” and “La muñeca menor,” both published in Papeles de Pandora (1976), as well as Ana Lydia Vega’s “Pasión de historia” (1982) I examine how women suffer the consequences of colonization through often-silenced violence. My analysis of their corpus shows how they push back against the literary old guard by denouncing gendered violence, condemning victim blaming, and encouraging female creation. As a whole, my dissertation aims to shed light on an often-silenced issue: the culture of misogyny embedded in Puerto Rico’s canonical literature and how it bleeds into gendered violence.