This article traces the provenance and the multiple layers of meaning, as well as the contradictions encoded, in the word filibustero from its origins among pirates in the Caribbean in the sixteenth and seventeenth centuries to the American military adventurers in the nineteenth century, whose complex politics intersected with proindependence Cuban exiles. This history illumines the word’s specific meaning as it entered the Philippines before 1872. At the same time, filibustero can be linked to the Manilamen, natives of the Spanish Philippines who worked as international seafarers, who became involved in mercenary activities, especially in Shanghai. This seaborne genealogy contextualizes the analysis of the filibustero in José Rizal’s second novel.