This study utilizes a Critical Anti-Race Qualitative Phenomenological Methodology to challenge the dominant deficit perspective which reinforces the notion that the cultural deprivation of Blacks causes their marginalization. From this viewpoint, Blacks should take individual responsibility for changing their life conditions. However, this article offers narratives of Black men that reveal how structural factors grounded in the notion of racial battle fatigue limit their autonomy, education, and access to employment opportunities. The study focuses on underemployed, second-generation Caribbean Black Male Youth between 18 years and 30 years of age who have made the post-high school transition into the labor market but remain underemployed. This study seeks to understand the central theme emerging in the counternarratives: "Caribbean Black Male Youth perceive and experience a lack of employment opportunities." This article's aim is to show how Caribbean Black Male Youth struggle to address their limited employment opportunities by exploring the impact of the intersecting politics of race, gender, and class on the City of Toronto labor force.