Abstract This underlying project aims to plumb Roxana’s predicament, rebellion and power struggle in the oppressive circumstance in the stance of a female capitalist in the early eighteenth-century patriarchal society. Her man-woman identity also unveils her inner desire to shrink from her former victimized passive role of the oppressed into a power-hunger hardened oppressor and emblemizes her inner desire to penetrate into the wider commercial world and monopolize the world’s wealth and power in the role of female capitalist. Roxana’s shame-ridden whore identity traps Roxana into the state of prisoner. She is always in fear. Roxana’s material accumulation cannot save her damaged ego. The success under Roxana’s belt is limited to material success, which cannot ascribe to her psychological salvation. The title of Roxana: The Fortunate Mistress is auspiciously a huge satire that the fortunate mistress’s life experience is basically grounded in unnamable mental disorder and she is mercy of neurotic fear of possible exposure. Roxana cannot secure mental peace because she is at enslaved by phobia of shame in mind. Chapter One elaborates poor women’s anxiety of economic independence in patriarchy society. The equal footing between men and women was eradicated by disfranchising women’s inborn rights of autonomy. I delve into the texts of Roxana to fathom how poor women secure self-sufficiency, and navigate their economic predicament and economic autonomy and sovereignty in and out the marriage system. Chapter Two manifests how Roxana executes her desire of becoming a man-woman and free agent in the patriarchy society. Her holds anguished spirit against economic constraint and sexual constraint women endure of the time. In the patriarchy society, hegemony was limited to men. I propose Roxana’s resolution of anti-convention signals her desire of anti-discrimination. Roxana’s desire of becoming a man-woman witnesses her drastic anger to shake off women’s passive and victimized role in patriarchy society. She breaches social normality and models men in sexuality with rebellious determination to reclaim her authority in the oppressive society. Chapter Three unmask the interplay between Roxana’s anxiety of her former criminal whore identity and the violence of Abjection. At the core, I chiefly fathom Kristeva’s essay “On the Melancholy Imaginary” and “The Power of Horror” (1982), coupled with Freud‘s psychological theory in A General Introduction to Psychoanalysis (1920) and accompanied with Elizabeth Groze’s essay “Sexuality and the Symbolic Order in Jacques Lacan” to decipher Roxana’s traumatic life in the context of identity crisis. Keywords: exploitation, patriarchy, hierarchy, Social oppression, social injustice, puritan capitalist, individualist, feminist, free agent, non-conformist, jouissance, violence of abjection, poverty and crime.