In this article, I argue that Du Bois’s Japan—despite displaying his myopic failure to critique non-Western imperialism—served as a potential model for his reimagining transnational democratic leadership beyond Western-centric models and their legacies of White supremacy and democratic despotism. Du Bois’s reflections from the 1890s to the 1960s generally demonstrate a sustained, seven decade-long fluid commitment to realizing a vision of transnational leadership that was accountable to the democratic masses, whether in Asia, Africa, the United States, or elsewhere. Such reflections hold importance now (even as they did in Du Bois’s time) as we continue to grapple with the legacies of Western “democratic” dominance, especially in international institutions designed to facilitate global governance.