Global biodiversity is changing rapidly driven by human alteration of habitat, and nowhere this is more dramatic than in insular habitats. Yet land-cover change is a complex phenomenon that not only involves habitat destruction but also forest recovery over different time scales. Therefore, we might expect species to respond in diverse ways with likely consequences for the reorganization of regional assemblages. These changes, however, may be different in tropical islands because of their low species richness, generalist habits and high proportion of endemics. Here, we focus on the island of Puerto Rico and ask how island-wide changes in land cover and land use has influenced the large-scale organization of bird assemblages. To address this question, we combined in a Geographical Information System (GIS) the first 6 years (1997–2002) of the Puerto Rican Breeding Bird Survey (PR-BBS) with land-cover and land-use data extracted from a published digital map derived from the classification of Landsat images. A Non-metric Multidimensional Scaling (NMS) ordination based on the composition and abundance of birds, and percentage land-use types showed that land use followed by climate could explain most of the variation observed among routes in terms of species composition and abundance. Moreover, endemic and exotic species were widely distributed throughout the island, but the proportion of endemic species is higher in closed forests while exotic species are more abundant in open habitats. However, historical accounts from the early 1900s indicate that endemic species were distributed across the entire island. Today, most of the land cover transformation in Puerto Rico occurs in the lowlands which may explain the high abundance of endemic species in cloud forests and the high abundance of exotic species in open habitats in the lowlands.