This case study of fatherhood in early nineteenth-century England examines the conflict between a wealthy East India Company merchant and his increasingly wayward adolescent son, who was transported to Australia in 1814. It argues that fatherhood was often necessarily a reactionary process, that did not conform to a static, historically specific model of ideal or dysfunctional fatherhood. It also traces the origins of much of the disagreement to conflicting ideals of masculinity between father and son, which were exacerbated by their rise in wealth and social status. Since both aspired to the elite status of gentleman, the article demonstrates that competing and compatible ideals can co-exist within different generations of the same family. Thus a study of male family experience suggests that hegemonic masculinity is subject to short-term shifts of emphasis on those values adopted by men of different ages and social status.