The characters in fictional works, too, are often fictitious, representing the products of an author’s imagination. Character development generally stems from the author’s psyche, whether it be subconscious or cognizant. Characters then, to varying degrees, inevitably manifest different aspects of the authors themselves. The author’s values, beliefs, experiences, fears, hopes and dreams are reflected in the development of each character, and one can cultivate a greater understanding of the work itself by understanding who the author is/was as a person. For this reason, a critical analysis of the psychological connections between James Joyce and the characters within his work, The Dead, specifically Gabriel Conroy, is an advantageous task to endeavor, as the process fosters a greater coherence of the concepts behind Gabriel and the themes his thoughts, actions, and speech are intended to represent. Joyce fixates on the character Gabriel Conroy throughout the short story, providing an in depth description of his appearance, personality, and blatant allusions to his education/livelihood by way of various conversations with other party guests and himself. Moreover, Joyce provides an omniscient narrative, unique to Gabriel, that delves deeper into the character’s thinking while providing the reader with insight into Gabriel’s insecurities, neuroticism, and fluctuating self-esteem. An educated professor and part-time book reviewer, Gabriel is described as wearing rimmed glasses,