A new, extinct genus of flea is described and figured in the tribe Spilopsyllini (Siphonaptera: Pulicidae) from a male preserved in Early Miocene Dominican amber. Eospilopsyllus kobberti Beaucournu & Perrichot, n. gen. and n. sp., is characterized by the absence of ctenidia, very small eyes, lanceolate terminal segment of the maxillary palpus, enlarged second abdominal sternite, legs with six notches on dorsal margin of tibiae, five pairs of lateral plantar bristles on distitarsomeres, and ungues with a reduced space between the basal lobe and the tarsal claw. Most of the extant spilopsyllines parasitize lagomorphs and squirrels, but these taxa were seemingly absent from the Greater Antilles until very recently. Instead, the Tertiary record and biogeographical history of land mammals on these islands suggests that early spilopsyllines may have parasitized the endemic solenodon insectivores or echimyid rats.