TO investigate why some lineages undergo evolutionary radiation, we compare the passerine avifaunas of the Hawaiian and Galapagos archipelagoes, which have supported well-known radiations of birds, with those of the Lesser Antilles, which have not. We focus on four steps required for the buildup of diversity through allopatric speciation and secondary sympatry: genetic divergence in isolation, persistence of island populations, recolonization of source islands, and ecological compatibility in secondary sympatry. Analysis of genetic divergence among island populations in the Lesser Antilles reveals evidence of both prolonged independent evolution and reexpansion of differentiated island populations through the archipelago but little evidence of secondary sympatry of divergent genetic lineages. Archipelagoes with high rates of colonization from continental or nearby large-island sources might fail to promote evolutionary radiations because colonists fill ecological space and constrain diversification through competition. However, morphological analysis demonstrated similar divergence between allopatric populations in species in Hawaii, Galapagos, and the Lesser Antilles, although the rate of divergence between secondarily sympatric species evidently is more rapid in Hawaii and the Galapagos. Alternatively, endemic buildup of diversity might be facilitated by the relative absence of pathogens in Hawaii and Galapagos that otherwise could prevent the secondary sympatry of populations owing to disease-mediated competition.