Alessandria was founded in 1168 with a charter as a free commune; it was sited upon a preexisting urban nucleus, to serve as a stronghold for the Lombard League, defending the traditional liberties of the communes of northern Italy against the Imperial forces of Frederick Barbarossa. Alessandria stood in the territories of the marchese of Montferrat, a staunch ally of the Emperor, with a name assumed in 1168 to honor the Emperor's opponent, Pope Alexander III. In 1174–75 the fortress was sorely tested by Imperial siege and stood fast. A legend (related in Umberto Eco's book Baudolino, and which recalls one concerning Bishop Herculanus’ successful defense of Perugia several centuries earlier) says it was saved by a quick-witted peasant, Gagliaudo: he fed his cow with the last grain remaining within the city, then took it outside the city walls until he reached the Imperial camp. Here he was captured, and his cow cut open to be cooked: when the Imperials found the cow's stomach filled with grain, Gagliaudo was asked the reason to waste such a rich meal. He answered that he was forced to feed his cow with grain because there was such a lot of it, and no room to place it within the city. The Emperor, fearing that the siege would last too long, left Alessandria free. (Malaria was probably the real cause of his departure.) A statue of Gagliaudo can be found on the left corner of the city cathedral.
Alessandria entered into jealous conflicts with the older communes of the region, in particular with Asti.
In 1348 Alessandria fell into the hands of the Visconti and passed with their possessions to the Sforza, following the career of Milan, until 1707, when it was ceded to the House of Savoy and henceforth formed part of Piedmont. The new domination was evidenced by the construction of a new big Cittadella on the left side of the river Tanaro, across from the city.
With Napoleon's success at the Battle of Marengo (1800), Alessandria fell to France and became the capital of the Napoleonic Département of Marengo. During this period another substantial fort was built to the north of the city containing impressive and substantial barracks which are still used as a military headquarters and stores (2006). The remains of a second fort to the south of the city (Cristo quarter) have been sliced in two by a railway (Forte ferrovia); a third one still remains in the middle of the same quarter (Forte Acqui).
From 1814 Alessandria was Savoyard territory once more, part of the Kingdom of Sardinia. During the years of the Risorgimento, Alessandria was an active center of the liberals. In a suburb, Spinetta Marengo, the Battle of Marengo is reenacted annually, on June 14.
Alessandria was the first capital of an Italian province to be governed by a Socialist: the clockmaker Paolo Sacco was elected mayor on July 25, 1899. Alessandria was a tactical military target during World War II and was subjected to intense Allied bombing, the most serious being the raids of April 30, 1944, with 238 dead and hundreds wounded, and April 5, 1945, with 160 deaths, among them 60 children from the children's asylum in Via Gagliaudo. On end of that month the city was liberated from the German occupation (1943–1945) by the partisan resistance and troops of Brazilian Expeditionary Force.
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