This essay highlights some of the unexpected leadership roles that women have played in relation to the oil industry on St. Croix in the U.S. Virgin Islands (USVI) from 1965 to the present. The people of St. Croix (Crucians) have a long and proud history of strong women as community and family leaders. Despite their invisibility in contemporary narratives of oil refining under U.S. colonialism on St. Croix, Crucian women have contested commonly held stereotypes of women’s roles and contributed to, as well as challenged, the refinery on their own terms. This article is part of a broader literature about women’s leadership across civil society, the private sector, and the public sector in the Caribbean and Latin America that focuses on women’s agency. This essay is also about the unequal situations that places like St. Croix face when negotiating with multinational corporations under colonial circumstances. While the oil industry generates income for the USVI, the refinery has environmental impacts injurious to the local population. Despite colonial, neocolonial, and patriarchal characteristics of their societies, women leaders on St. Croix, across the Caribbean, and Latin America have been a constant phenomenon, not just a recent occurrence. All the women in this essay demonstrate the centrality that women’s guidance, leadership, and actions play in the fostering, functioning, and protection of families, communities, and public and private institutions on St. Croix. The women in this essay created their own opportunities and took matters into their own hands, demonstrating alternative expressions of self and community values, as well as local action and agency, whether through personal relations, labor protests, stringent economic negotiations, occupying political office, and/or community-based activism.