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The origins of the town of Grosseto belong to the High Middle Ages. It was a fief of the Counts Aldobrandeschi in 803: a document recording the assignment of the church of St. George to Ildebrando degli Aldobrandeschi reports this fact.

Grosseto grew in importance after the decline of Rusellae and Vetulonia until it was one of the principal Tuscan cities. In 1137 the city was occupied by German troops, led by duke Henry X of Bavaria.

In 1151 the citizens swore loyalty to Siena, and in 1222 the Aldobrandeschi gave the Grossetans the right to have their own representatives and authorities. In 1244 the city was reconquered by the Sienese, and its powers, together with all the Aldobrandeschi's imperial privileges, were transferred to Siena by order of the imperial vicar. It became an important stronghold, and the fortress (rocca), the walls and bastions can still be seen.

In 1266 and in 1355, Grosseto tried in vain defeat Siena. Umberto and Aldobrandino Aldobrandeschi tried to regain Grosseto for their family. Anyway the Sienese army won, and in 1259 Siena elected a Sienese authority to control Grosseto. But Grosseto gained its freedom in the following year and fought in alliance with the Florentine forces in the Battle of Montaperti.

During the following 80 years Grosseto was occupied, ravaged, excommunicated by Pope Clement IV, freed in a republic led by Maria Scozia Tolomei, besieged by emperor Louis IV and by the antipope Nicholas V in 1328, until it finally submitted to its more powerful neighbour, Siena.

The pestilence of 1348 struck Grosseto hard and by 1369 its population was reduced to some hundred families. Its territory, moreover, was frequently ravaged, notably in 1447 by Alfons V of Sicily and in 1455 by Jacopo Piccinino.

Sienese 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 defensive walls was begun, which are still well preserved today, while the surrounding wetlands were drained. Grosseto, however, remained a minor town, with only 700 inhabitants at the beginning of the 18th century.

Under the rule of the House of Lorraine, Grosseto finally evolved, so that it gained the title of capital of the new Maremma province.



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