I will illustrate how we can combine phylogenetic analyses of biogeography and phenotypic trait evolution to better understand the assembly of ecological communities. I will focus on two questions. First, how have the set of species with their given set of ecological traits come to be present in the same local community? For example, how important is in-situ evolution of characters within the community relative to dispersal of traits from elsewhere, and when will one process be more important than the other? Second, how does the composition of the community influence trait evolution in the species that occur there and the propensity of the community to be invaded by other species? Our studies so far illustrate what may be several general principles of community assembly, when viewed from this phylogenetic perspective. For example, one surprising (but recurring) inference from these studies is that even though competition seems to be important in driving and constraining phenotypic evolution, it often fails to prevent the co-existence of similar species in the same community. I call this the competition-divergence-coexistence conundrum.