This article examines the complex life of one of the Universal Negro Improvement Association’s most charismatic but undertheorized figures, Madame Maymie Leona Turpeau de Mena. Relegated to the footnotes of UNIA history, the existing version of de Mena’s biography identifies her as an Afro-Nicaraguan immigrant who rose to the upper echelons of the UNIA. After years of serving as assistant international organizer and electrifying audiences throughout the hemisphere, she eventually assumed control of all the North American chapters of the UNIA, the editorship of the Negro World, and acted as Marcus Garvey’s representative in the United States and globally. Recently uncovered archival materials reveal that de Mena was actually born in St. Martinville, Louisiana, in 1879. How could such a prominent UNIA figure vanish from the historical record only to reappear and be so misunderstood? Part of the dilemma lies in the fact that de Mena appears to have intentionally altered the key elements of her biography to reflect her changing personal life and political commitments. This article maps de Mena’s shifting racial and political subjectivities as a transnational proto-feminist, moving through the landscapes of the U.S. Gulf South, Caribbean Central America, the U.S. Northeast, and preindependence Jamaica. It provides a critical corrective to de Mena’s existing biography and examines how black women moved through transnational political and cultural movements of the early twentieth century, authoring themselves into existence through intimate and public acts of diasporic self-making.