The London planetree is one of the most common street trees in the world. The history of this tree in Philadelphia sheds light on the intersecting cultural, political, economic and ecological drivers of species selection decisions, as well as the various actors involved in those decisions. The London planetree, misidentified as Oriental plane, was enormously popular in the early twentieth century due to its large stature, tolerance of air pollution, and lack of pest problems, as well as an affinity for Paris and London. Botanists, horticulturalists and foresters established the plane’s reputation as a reliable street tree, which was then echoed by marketing from nurseries. The planting of large shade trees, including the plane, was also touted as a sound return on investment for real estate developers. However, the tree lost prominence over time due to a fungal disease as well as tree professionals’ shifting priorities. Urban foresters today promote diverse planting palettes and smaller-stature trees which have fewer infrastructure conflicts, making streetscapes with monocultures of large shade trees an artifact of the past. Our investigation provides insights into the multi-stakeholder networks and deeply intertwined social and environmental drivers that shape street tree populations.