Community and biogeographic surveys often conclude that plant-pollinator interactions are highly generalized. Thus, a central implication of the pollination syndrome concept, that floral trait evolution occurs primarily via specialized interactions of plants with their pollinators, has been questioned. However, broad surveys may not distinguish whether flower visitors are actual pollen vectors and hence lack power to assess the relationship between syndrome traits and the pollinators responsible for their evolution. Here we address whether the floral traits of three closely related hermaphroditic Silene spp. native to eastern North America (S. caroliniana, S. virginica, and S. stellata) correspond to predicted specialized pollination based on floral differences among the three species and the congruence of these floral features with recognized pollination syndromes. A nocturnal/diurnal pollinator exclusion experiment demonstrated that all three Silene spp. have diurnal pollinators, and only S. stellata has nocturnal pollinators. Multiyear studies of visitation rates demonstrated that large bees, hummingbirds, and nocturnal moths were the most frequent pollinators of S. caroliniana, S. virginica, and S. stellata, respectively. Estimates of pollen grains deposited and removed per visit generally corroborated the visitation rate results for all three species. However, the relatively infrequent diurnal hawkmoth pollinators of S. caroliniana were equally effective and more efficient than the most frequent large bee visitors. Pollinator importance (visitation X deposition) of each of the animal visitors to each species was estimated and demonstrated that in most years large bees and nocturnal moths were the most important pollinators of S. caroliniana and S. stellata, respectively. By quantifying comprehensive aspects of the pollination process we determined that S. virginica and S. stellata were specialized on hummingbirds and nocturnal moths, respectively, and S. caroliniana was the least specialized with diurnal hawkmoth and large bee pollinators. Compared across the Silene species, divergent floral character states are consistent with increasing the attraction and/or pollen transfer efficiency of their respective major pollinators, which suggests that the pollinators are past and/or contemporary selective agents for floral trait evolution in these three Silene species. We conclude that the pollination syndrome concept allows us to effectively relate the functional significance of floral morphology to the major pollinators of these Silene species.