Recent phylogenetic advances have uncovered remarkable biogeographic histories that have challenged traditional concepts of dispersal, vicariance and diversification in the Greater Antilles. Much of this focus has centred on vertebrate lineages despite the high diversity and endemism of terrestrial arthropods, which account for 2.5 times the generic endemism of all Antillean plants and non-marine vertebrates combined. In this study, we focus on three Antillean endemic praying mantis genera, Callimantis , Epaphrodita and Gonatista , to determine their phylogenetic placement and geographical origins. Each genus is enigmatic in their relation to other praying mantises due to their morphological affinities with both Neotropical and Old World groups. We recovered the three genera as a monophyletic lineage among Old World groups, which was supported by molecular and morphological evidence. With a divergence at approximately 107 Ma, the lineage originated during the break-up of Gondwana. Ancestral range reconstruction indicates the lineage dispersed from an African + Indomalayan range to the Greater Antilles, with a subsequent extinction in the Old World. The profound ecomorphic convergence with non-Caribbean groups obscured recognition of natural relationships within the same geographical distribution. To the best of our knowledge, the lineage is one of the oldest endemic animal groups in the Greater Antilles and their morphological diversity and restricted distribution mark them as a critical taxon to conserve.