The drawings shown here have evolved over time from simple scaled documentation of trees as monuments, into a series of visual essays about the early role trees have played in the evolution of the city in the American Tropics. Each tree introduces an essay on a significant threshold in the development of the city. As an example, the native Ficus aurea / Strangler fig has historically been introduced as a botanical oddity or ‘freak’ of the American tropics and was frequently cited by naturalists as an exotic representative of the monstrous and bizarre riches of the tropical hammock – a place paradoxically both ideal for development because of the richness of its soil but difficult and expensive to clear. By contrast the Maleluca was introduced as a way to drain the Everglades and was boasted to be a cash crop for medicinal purposes becoming instead a marker of our early attitudes about careless land development practices that we are still addressing today. The research purpose of the drawings is to underscore how our attitudes about the city have been intertwined with our attitudes about landscape and more importantly how specific species of trees have figured prominently in this history. While the work is ongoing it is hoped that there will be a book one day on how trees as well as urban plans and buildings, have built the city.