This study considers the social and economic lives of free women in Jamaica from 1760 to 1834. Throughout the period studied Jamaica was Britain’s most important imperial holding. The colony’s slave economy, driven by the labour of hundreds of thousands of enslaved men and women, generated incredible wealth. Still, Jamaica was the deadliest place to live in British America. Due to the endemic nature of tropical disease and atrocious mortality rates, neither the enslaved population nor the white population maintained itself naturally prior to emancipation. However, an environment characterized by death and demographic crisis engendered heightened opportunities for women to take part in tropical enterprise and to shape the futures of their families. Inheritance norms were weakened by the omnipresence of death, precipitating more generous inheritance bequests for women and a greater role given to wives and daughters—both white women, and those of mixed-race descent—in tropical commerce. Additionally, as slave ownership was not limited by gender or race, free women of all races took part in the slave economy. Free women’s visibility in the island’s formal as well as informal economies, and the wealth accumulated by some, was unsurpassed in a British American context. However, in this slave society, free women’s prosperity rested upon the exploitation and oppression of others. In contrast to familiar historical trajectories that have presented Caribbean participation in Atlantic markets of slavery and capital as male-driven ventures, this study argues that free women of all races were vital participants in the slave economy and principle beneficiaries of plantation profits. This project moves beyond previous studies on women in colonial Jamaica by revealing how women’s enterprise and relations with one another shaped the nature of this economy and society, including the commercial, familial and kin networks that bound it together. In doing so, it enhances our understanding of this colony and the operation of race and gendered power within it.