Any given tree has huge numbers of interactions. Insects munch leaves, fungi help gather nutrients in exchange for food, and bacteria abound. But what happens if a tree is moved out of its native range and grown on a different continent? Based on years of data on invasive species and observations of ornamentals, researchers know that non-native trees tend to have fewer interactions. The question I seek to answer is: How do non-natives, such as ornamental trees, gain or lose species interactions over years, centuries, and millennia? My research team and I are assessing this process for trees in New York City. Using contemporary sampling and historical specimens, we have found that species interactions with trees are far from static. For instance, herbivory in non-native trees has increased over centuries, but not reached the levels experienced by native species. Fungi that live in leaves of non-native trees, however, seem to have more diversity but likely less specialization compared to their counterparts on native leaves. Our results can help predict the long-term consequences for food webs of planting non-native species or native species within our cities and other landscapes.