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The origins of Grosseto go back to the Middle Ages. In 803 a document states the assignment of the church of St. George to Ildebrando degli Aldobrandeschi, whose successor where counts of the Grossetana Marquisdom until the end of the 12th century. In 1151 the citizens swore loyalty to Siena and in 1222 the Aldobrandeschi gave the citizens the right to have a podesta' (a kind of mayor) of their own. In 1244 the city passed under the control of Siena, and was as the rest of Tuscany was a field of battle between Guelph and Ghibelline parties.
The pestilence of 1348 struck Grosseto, whose population in 1369 had reduced to some hundred families. The Senese rule ended in 1559, when Charles V handed over the whole duchy to Cosimo I de Medici, first Grand Duke of Tuscany. In 1574 the construction of a line of walls was begun, which is still today well preserved, while the surrounding plain was dried. Grosseto, however, remained a second rate town, with only 700 inhabitants at the beginning of the 18th century. Under the rule of the House of Lorraine, Grosseto flourished, and in 1766 was given the title of capital of the new Maremma province.