Glenn Loury reflects on his memoir, Late Admissions, and the process of recalling his life experiences. He discusses the powerful and galvanizing experience of reliving his past, including memories of his mother, admiration for his father, and personal struggles with addiction and infidelity. The conversation then shifts to the transformation of the South Side of Chicago over time and the unraveling of the Black family structure. The impact of cultural and societal changes, as well as class differences, on the decline of the Black family is explored. The chapter concludes with a discussion on the contrasting experiences of Black students at Northwestern University and the sense of wonder and entitlement among different socioeconomic backgrounds. The conversation covers various topics including personal experiences with racial identity, addiction and recovery, the debate between Booker T. Washington and W.E.B. Du Bois, the influence of Thomas Sowell, and the collaboration between Glenn Loury and John McWhorter.