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After the 1348 Black Death, the Republic of Siena went through a period of recurrent plagues, military threats, and famines. During this phase the city moved from the oligarchic system to a coalition formed by the participation of social groups previously excluded from politics, an institutional path almost unique among contemporary Italian states. Did the city maintain its fiscal capacity, and, if so, how? These questions are addressed using a quantitative analysis of a new dataset compiled from the fiscal archives of the city of Siena, which shows two main results. First, despite the increasing external threats, the coalitions were able to maintain fiscal capacity until the second half of the fifteenth century. Second, they did so by adopting progressive fiscal instruments that allowed the city to raise the resources needed to deal with increasing fiscal pressure. However, these instruments ultimately linked the fiscal capacity of Siena to the economic trends of northern and central Italy. When in the second half of the fifteenth century the region entered into an economic downturn, the fiscal capacity of Siena plummeted and the city lost its independence.