In 1948, three Haitians became Rockefeller Foundation Fellows: Jean Chenet for museum studies, and Maurice Borno and Luce Turnier for painting. These fellowships were absolutely groundbreaking for several reasons: foremost that the Rockefeller Foundation had never before granted fellowships in museum studies or to visual artists, and their granting lent credence to Haiti’s burgeoning art scene. Artistic renown requires institutional support through mechanisms that bestow prestige, such as exhibition records, scholarly publications, and, significantly, grants and fellowships. Such mechanisms have been difficult to access for artists who are racially and geographically on the margins. By tracing the history and results of these Rockefeller Foundation fellowships, this article examines the interpersonal relationships that map onto greater structures that needed to be negotiated for such prestigious awards to become a reality. Specifically, the awarding of these fellowships to three Haitians illuminates a crossroads intersected by economic, linguistic, racial, and gendered biases.