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The ushkuiniks (Russian: ушкуйники) were medieval Novgorodian pirates who led the Viking-like life of fighting, killing, and robbery. Their name derives from "ushkui", a type of flat-bottom medieval Finnish ship Uisko (literally ; swimming snake), which could be easily transported over portages between the rivers.

Although the Novgorodians took part in the Tsargrad expeditions of the 10th century and mounted pillaging raids to Finland in the 12th century, the ushkuiniks first appear as an organized force in the 1320s. Arranged in squadrons which could number several thousand, the ushkuiniks enjoyed the patronage of influential boyar families of Novgorod, who used them to demonstrate Novgorod's military clout to its neighbours and to advance its trade interests in the Volga region.

During the famous campaign of 1360, the ushkuiniks sailed from Novgorod by the portages to the Volga river. Under command of boyar Anfal Nikitin, they gained possession of Zhukotin, a trade emporium in Volga Bulgaria. A ruler of the Golden Horde, which controlled Zhukotin, was furious and ordered Grand Prince Dmitry Konstantinovich to capture the ushkuiniks and to bring them to the Horde for trial, but Dmitry's punitive expedition failed.

In 1363 the pirates launched the first Novgorodian raid along the Ob River. Three years later, without consulting their superiors in Novgorod, they approached Nizhny Novgorod and, wishing to punish Dmitry for his hostile action, massacred Armenian and Tatar merchants trading there. This led to a diplomatic row, when Dmitry demanded apologies from Novgorod Republic.

In 1371, the ushkuiniks sacked Yaroslavl, Kostroma and other Upper Volga cities. Three years later, they sailed with upwards of ninety ships to pillage the Vyatka region. In 1375, they defeated the militia of Kostroma and burnt the city to the ground. The destruction was so severe that Kostroma had to be rebuilt elsewhere. After that, they looted Nizhny Novgorod and sailed down the Volga to Astrakhan, where they were annihilated by a Tatar general.

By 1391, the ushkuiniks had recovered from this reverse and felt strong enough to resume their activities. That year, they sacked both Zhukotin and Kazan. With Muscovy's power on the ascendant, however, Novgorod Republic was pressed into putting down their filibustering activities in the first decades of the 15th century.

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