Caribbean Anolis lizards are a classic case of adaptive radiation, repeated four times across islands of the Greater Antilles. On each island, very similar patterns of evolutionary divergence have occurred, resulting in the evolution of the same set of ecological specialists—termed ecomorphs—on each island. However, this is only part of the story of the Caribbean anole radiations. Indeed, much of the species diversity of Caribbean Anolis occurs within clades of ecomorphs, which contain as many as 14 ecologically-similar species on a single island. We ask to what extent the classic model of ecological interactions as the driving force in adaptive radiation can account for this aspect of anole evolutionary diversity. Our answer is that it can in part, but not entirely. More generally, the most complete understanding of evolutionary diversification and radiation is achieved by studying multiple hierarchical evolutionary levels from clades to populations.