Roberta Jackson’s critique of “A Painful Case” argues that James Duffy is a symbol of sexual oppression. A product of his time, Duffy is defined as an individual oppressed by the moral codes and standards of his time. Jackson supports her argument by referring to James Joyce’ personal life, and in particular, the sexual tendencies of his brother Stannie. Not only does this provide Jackson with cultural and historical background into the life of Joyce, but rather, furthers her argument by asking several insightful questions. Throughout her critique, Jackson includes the analysis of several other individuals. This not only establishes a variety of lenses to view the text, but also, allows for Jackson to develop and strengthen her argument. In particular, one critique comes from Charles Peake, in which he defines James Duffy as an “upright and incorruptible man, who freely chooses the cold, dark, silent world of his isolation.” This reading spoke out to me, especially having read Hemingway’s ‘The Sun Also Rises’ prior to this assignment. I could not agree anymore with Peake in believing that this is an internalized oppression chosen by Duffy. Many scholars find Duffy to display homosexual tendencies that of which are applicable to the life of Joyce. However, I find James Duffy to be a realist, a lonely individual that both paradoxically ‘unites him with and separates him from others’. He is simply ahead of his time, and looking out for himself. James possesses sexual desire but fails to act on it. Although this may be credited to fear and the instability of the times, I find this rejection of Mrs. Sinico as an act of protection. A protection from anguish and misery in order to uphold the realistic worldview James Duffy has come to develop. Ultimately, James is a man who lacks emotion, drive, and all romantic values. He does not reject Mrs. Sinico due to homosexual preferences, but rather, sees the lack of fulfillment that stems from such interaction.