In Chapter 14, MacLeod revisits Clarendon Heights and its residents after significant time has passed, reflecting on how social structures continue to shape opportunities and constraints for the Brothers and the Hallway Hangers. This reflection begins with a conversation between MacLeod and Isaac, a successful alumnus of the neighborhood, who challenges the notion that middle-class attainment for a few individuals from the community is an exceptional achievement. This dialogue sets the stage for a deeper exploration of social reproduction, a theme analyzed by Katherine McClelland and David Karen rather than MacLeod himself, due to his current commitments as a parish priest.

The authors explore the lives of the men, now in their forties, revealing how their paths have been shaped by their social class, educational opportunities, and personal choices. They discuss significant life events and transitions, such as employment, marriage, fatherhood, and the struggles with addiction and the criminal justice system. The narrative particularly focuses on the varying degrees of economic stability they have achieved, with some members breaking into middle-class jobs while others remain mired in poverty or near-poverty conditions.

The chapter emphasizes the persistent influence of structural factors on individual lives, highlighting how early decisions and social capital play crucial roles in shaping adult outcomes.