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The article explores the vibrant constitutional community that existed in St. Augustine and the province of East Florida in the final decade of Spanish control of the area. Based on relatively unexplored primary sources, it reveals a great deal of unknown information about the importance of the Constitution in Florida immediately before the territory was transferred to the United States. The article provides full description of the Constitution's promulgation in 1812 and a second promulgation of the Constitution in 1820 (something unknown in the general literature). It also addresses the construction of the St. Augustine monument to the Constitution erected in 1813 and standing today in the central square of the city. It concludes with the novel claim that when Spain transferred the territory to the United States in 1821, the territory moved from one constitutional regime, under the Constitution of Cadiz, to another, under the Constitution of Philadelphia. This article presents a very different view of the Spanish period from the standard account, which usually links Spain's presence in North America with royal absolutism and a lack of meaningful governmental development. It ends by suggesting that there may have been Spanish and North American influences in constitutional thought in both directions that merit further exploration on the state and national level.