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Kiev (also spelled Kyiv,) is one of the oldest and most important cities of Eastern Europe and has played a pivotal role in the development of the medieval East Slavic civilization.

The city is thought to have existed as early as the 5th century, initially as a growing trading post. The legend of Kyi, Schek and Khoryv speaks of a founder-family consisting of a Slavic tribe leader Kyi, the eldest, his brothers Schek and Khoriv, and also their sister Lybid, who founded the city. Kyiv/Kiev is translated as "belonging to Kyi".

It is unclear when Kiev fell under the rule of the Khazar empire but the Primary Chronicle (a main source of information about the early history of the area) mentions Slavic Kievans telling Askold and Dir that they live without a local ruler and pay a tribute to Khazars in an event attributed to the 9th century. At least during the 8th and 9th centuries Kiev functioned as an outpost of the Khazar empire. A hill-fortress, called Sambat was built to defend the area. At some point during the late ninth or early tenth century Kiev fell under the rule of Varangians and became the nucleus of the Rus' polity.

Gradually acquiring the eminence as the center of the East Slavic civilization, Kiev reached its Golden Age as the center of Kievan Rus' in the tenth through the twelfth centuries. Its political, but not cultural, importance started to decline somewhat when it was completely destroyed during the Mongol invasion in 1240. In the following centuries Kiev was a provincial capital of marginal importance in the outskirts of the territories controlled by its powerful neighbors: the Grand Duchy of Lithuania, the Polish-Lithuanian Commonwealth and the Muscovite Russia. A Christian city since 988, it still played an important role in preserving the traditions of Orthodox Christianity, especially at times of domination by Catholic Poland.

From Oleg's seizure of the city until 1169 Kiev was the capital of the principal East-Slavic state, known as Kievan Rus' (or Kyivan Rus') which was ruled by initially Varangian Rurikid dynasty which was gradually Slavisized. The Kievan Grand Princes had traditional primacy over the other rulers of the land and the Kiev princehood was a valuable prize in the intra-dynastic rivalry. In 968 the city withstood a siege by the nomadic Pechenegs. In 988 by the order of the Grand Prince Vladimir I of Kiev (St. Vladimir or Volodymyr), the city residents baptized en-masse in the Dnieper river, an event the symbolized the Baptism of Kievan Rus'. Kiev reached the height of its position of political and cultural Golden Age in the middle of the 11th century under Vladimir's son Yaroslav the Wise. The following years were marked by the rivalries of the competing princes of the dynasty and weakening of Kiev's political influence, although Kiev temorarily prevailed after the defeat of the Polotsk at the Battle on the river Nemiga that also led to the burning of Minsk, in a later war (1169) Kiev was sacked by the Suzdalian troops of Andrei Bogolyubsky.

Devastated by the invading Mongols in 1240, it subsequently passed under the rule of the state of Halych-Volynia (prior to 1264) before falling to Gediminas (Gedimin) in 1321. Gediminas' brother Fiodor of Kiev was installed to rule the city. In 1362 Kiev became a part of the Grand Duchy of Lithuania after the Algirdas' victory against the Golden Horde in the Battle at Blue Waters. During the 15th century Kiev has been ruled by Olelkovich dukes, successors of the Grand Duke of Lithuania Algirdas. By the order of Casimir Jagiellon, the Duchy of Kiev was abolished and the Kiev Voivodship was established in 1471. Lithuanian statesman Martynas Goštautas was appointed as the first voivode of Kiev the same year; his appointment was met by hostility from locals.