Competition has negative effects on population size and also drives ecological character displacement, that is, evolutionary divergence to utilize different portions of the resource spectrum. Many species undergo an annual cycle composed of a lean season of intense competition for resources and a breeding season. We use a quantitative genetic model to study the effects of differential reproductive output in the summer or breeding season on character displacement in the winter or nonbreeding season. The model is developed with reference to the avian family of Old World leaf warblers (Phylloscopidae), which breed in the temperate regions of Eurasia and winter in tropical and subtropical regions. Empirical evidence implicates strong winter density-dependent regulation driven by food shortage, but paradoxically, the relative abundance of each species appears to be determined by conditions in the summer. We show how population regulation in the two seasons becomes linked, with higher reproductive output by one species in the summer resulting in its evolution to occupy a larger portion of niche space in the winter. We find short-term ecological processes and longer-term evolutionary processes to have comparable effects on a species population size. This modeling approach can also be applied to other differential effects of productivity across seasons.