Toucans are known for their predatory behavior, and urbanization can provide encounters with potential prey species that they would probably not meet in their usual natural habitats. Here, we describe a series of events of the Channel-billed Toucan (Ramphastos vitellinus) preying on eggs and nestlings of the Pale-breasted Thrush (Turdus leucomelas). The events occurred in a large forest fragment surrounded by an urban matrix in the Amazonian city of Manaus, Brazil. Urbanization has led to new challenges for many animals, including birds. The events reported here exemplify some of these challenges, such as the adaptation of a toucan or a population of toucans to exploit different food resources and find new prey in a modified environment, and the pressure of a new predator on the reproductive success of a thrush population. These new challenges may result in other adaptations and behaviors that must be investigated, as they can reveal patterns, impacts, or novelties on bird species and even on avian communities related to urbanization.