The history of organized boxing in colonial Kenya is complicated. The complexity stems from multiple facets undergirding colonialism. Until the last decade of British colonial rule in Kenya (1953–1963), organized boxing belonged to a tiny cadre of opulent white settlers in the colony. It became a sport for Blacks in the mid-1950s, especially impecunious Africans who appeared to colonial officials as lacking the qualities constituting morally acceptable citizens. This observation challenges the insinuation that British colonizers—administrators, missionaries, and settlers—introduced organized boxing in colonial Kenya exclusively for the indigenous people. This essay historicizes boxing in colonial Kenya (1895–1963). It is a socio-cultural history that grounds boxing within the broader history of colonization and contributes to the general history of sports and imperialism in Africa. The dynamics of class, race, citizenship, gender, power, and masculinity flow through the essay. Boxing in colonial Kenya is undocumented and undertheorized. The present work attempts to break this circle.