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Using government records and women's testimonies archived in private institutions, this article studies brothel keeping as business and brothel keepers as business owners and managers. In nineteenth-century Hong Kong, a military outpost of the British Empire, a commercial center attracting men of all classes and all nationalities, and yet, a stronghold of Chinese patriarchal practices, prostitution and brothel keeping flourished. The brothel keeper, always a woman, was offered an unprecedented opportunity to develop personal and entrepreneurial skills. In the process she expanded her life aspirations and played new roles in society and at home.