Comparing models of trait evolution might generate new insights into the role of evolutionary history in biological invasions. Assumptions underlying Darwin's naturalization conundrum suggest that close relatives are functionally similar. However, newer work is suggesting more complex relationships between phylogenetic and functional distance. We present an example in which communities of close relatives are functionally divergent in leaf traits and have greater invader biomass. Such an approach leads to new questions, such as: When might selection lead to divergence between close relatives? For example, a history of sympatry might correspond with divergence. We suggest that moving beyond a simplistic version of Darwin's naturalization conundrum as alternative hypotheses will lead to a more nuanced view on how evolution has shaped biological invasions.