The history of Kyiv from the Battle of Blue Waters (1362/3) until the end of the Khmelnytsky Uprising (1648–1657) encompasses Kyiv's period as part of the Grand Duchy of Lithuania (1362/3–1569), the Crown of the Kingdom of Poland within the larger Polish–Lithuanian Commonwealth (1569–1648), and the early revolutionary period of the Cossack Hetmanate during the Khmelnytsky Uprising. This Lithuanian–Polish–Cossack timeframe was preceded by Kiev in the Golden Horde period (1240–1362/3), and was succeeded by the history of Kyiv (1657–1811), at the times of the Ruin (1657–1687), the hetmanship of Ivan Mazepa (1687–1708), and the gradual liquidation of the autonomy of the Cossack Hetmanate (completed in 1764).
The complex nature of urban life in Kiev was a consequence of the city's border location. In general, the city did not lose its importance as a major commercial, economic and cultural centre of the Ukrainian lands. It was the capital of the Principality of Kiev until 1471, and thereafter of the Kiev Voivodeship. On the other hand, Chyhyryn would be chosen as the capital city of the early Cossack Hetmanate in 1649.
History Late 14th century
Following the Battle of Blue Waters (1362/3), Algirdas gained control of Kyiv and the Duchy of Podolia. Vladimir Olgerdovich (Volodymyr Olherdovych) was Grand Prince of Kiev from 1362 to 1394. During his reign, the Principality of Kiev extended across the lands of Kiev, Chernigov (modern Chernihiv), and parts of Polesia (Polissia). It included the cities of Zhytomyr, Vruchi, Turaŭ, Mogilev, Bryansk, Trubchevsk, Novhorod-Siverskyi, Kursk, Chernigov, Rylsk, Putyvl, Korsun, and Pereiaslav. Vladimir pursued a policy aimed at the independence of the Kievan Principality and expressed the interests of local secular and ecclesiastical feudal lords. During this time, Kyiv Castle was built on Zamkova Hora, and the Kievan prince minted his own coins. During this period, nomads rarely appeared in the Kievan region. This contributed to the development of agriculture, trade, and crafts in the Dnieper region and Kiev in particular.
Given the complex geopolitical situation of the Grand Duchy of Lithuania in 1385, the Union of Krewo was concluded between the Grand Duchy and the Kingdom of Poland, according to which, through the dynastic marriage of the Lithuanian Grand Duke Jagiełło and Queen Jadwiga of Poland, Jagiełło received the title of King of Poland, and Lithuania and Poland entered into a personal union.
At a meeting in Belz in 1392, it was decided to liquidate the appanage principalities in the Ruthenian lands by exchanging lands. Skirgaila (previously the Duke of Trakai, 1382–1395) gave Vytautas the Great his own lands in Lithuania and the Principality of Polotsk (after 1508 the Polotsk Voivodeship). In return, Skirgaila Olgerdovich received the Kievan region, as well as part of Podolia and the Principality of Volhynia (Volyn'). At the end of 1394, Prince Vladimir Olgerdovich of Kiev received a small portion of Polesia with the towns of Kapyl and Slutsk. In the autumn of 1395, Skirgaila carried out a successful campaign against the Golden Horde, resulting in the annexation of Cherkasy and Zvenyhorod.
After Skirgaila's death in 1397, Vytautas became the sole ruler of the Grand Duchy of Lithuania, while the Kievan region was ruled by Ivan Olshansky from 1397 to 1401. In the last years of the 14th century, the Grand Duchy of Lithuania became the most powerful state in Eastern Europe.
15th century Grand Duke Vytautas initiated several campaigns against the Golden Horde, even after his defeat at the Battle of the Vorskla River in 1399. Kiev became the main centre for gathering the forces of Vytautas and his allies. Vytautas strengthened the defensive structures of Kiev. During 1401–1433, the Olshansky princes and reigned in Kiev. Vytautas' active interference in the internal politics of the Golden Horde led to a large campaign by the forces of the Horde emir Edigu against the Kievan region and Kiev itself in 1416. Podil and the Upper City were captured, but the Kyiv Castle held out.
After Vytautas' death in 1430, the elected Grand Duke of Lithuania Švitrigaila began a policy of breaking the union with Poland and restoring the independence of the Grand Duchy of Lithuania and Rus'. Kiev became the main base of Prince Švitrigaila's 'Ruthenian party' on the eve of the Lithuanian Civil War (1432–1438). As a result of this war, Kiev, Siveria, Volhynia, Podolia, Polotsk, Smolensk and other Ruthenian lands united into the , independent from Kraków and Vilnius, and recognised the authority of Švitrigaila. In 1435, Švitrigaila lost the Battle of Wiłkomierz against his rival Sigismund Kęstutaitis, resulting in the collapse of the Grand Duchy of Ruthenia and the Principality of Kiev. In 1436, the people of Kiev rebelled, and in the same year, the Kievan voivode Yursha defeated the Lithuanian army near Kiev. Nevertheless, Švitrigaila was losing his influence in the Ruthenian principalities, and attempted to reconcile with Poland in September 1437: he would reign the lands that still supported him (chiefly Kiev and Volhynia) and after his death the territories would pass to the King of Poland. However, the Polish Senate did not ratify this treaty under strong protest from Sigismund Kęstutaitis. Švitrigaila retreated to Moldavia in 1438.
In 1440, the Kievan Principality was restored, headed by Prince Aleksandras Olelka from the Gediminid clan. During the reign of Prince Olelko (1440–1455) and Semen Olelkovich (1455–1470), the principality enjoyed relative independence. Kiev experienced an economic and cultural boom, becoming a major centre for the development of crafts and trade. During this period (1470), the stone architecture of the Kievan Rus' era was rebuilt and restored, in particular Saint Sophia Cathedral and the Dormition Cathedral.
After the Council of Ferrara-Florence (1438–1445), which was convened to conclude a union between the Western and Eastern Christian churches, Metropolitan Isidore was in Kiev, already holding the titles of papal legate and cardinal. The Prince of Kiev, Oleklo, welcomed the Union of Florence, and the Metropolitan solemnly proclaimed the union in Kiev. However, although he did not encounter strong resistance, the Orthodox continued to avoid Catholic churches.
In 1458, after the schism of the Metropolis of Moscow and all Rus' from the mother church, the Ecumenical Patriarchate of Constantinople, the Muscovite hierarchs lost the right to bear the title "Metropolitan of Kiev". Kiev became the nominal centre of the Metropolis of Kiev, Galicia and all Rus' (1441–1596), although the metropolitans often continued to reside in Navahrudak, the former seat of the Metropolis of Lithuania. Metropolitans held the title Metropolis of Kiev, Galicia and all Rus', and the first metropolitan with this title was Gregory the Bulgarian.
After the death of Prince Semen Olelkovich in 1471, Grand Duke of Lithuania and King of Poland Casimir IV Jagiellon abolished the Principality of Kiev, transforming it into the Kiev Voivodeship. In 1471, the people of Kiev protested against the abolition of the principality and tried to prevent Martynas Goštautas, the first Voivode of Kiev, from entering the city. A permanent Lithuanian garrison was stationed in the castle. In 1481, princes led by Mikhailo Olelkovich conspired to kill Grand Duke of Lithuania Casimir IV and restore the appanage principalities, primarily Kiev. The conspiracy was exposed, and Prince Mikhailo was beheaded in Kiev.
In 1482, by Crimean Tatar troops under the command of Crimean Khan Meñli I Giray at the request of the Grand Prince of Moscow, Ivan III. Most of the old Kievan churches were destroyed. Saint Sophia Cathedral was looted. The Crimean khan presented the Muscovite prince with a golden diskos and chalice, which the Tatars took from the cathedral. Ivan III provoked the Crimean khan to further attacks, which took place in the late 15th and early 16th centuries and greatly slowed down the development of Kiev.
In 1494~1497, Grand Duke of Lithuania Alexander Jagiellon granted the city of Kiev the right to self-government (Magdeburg rights).
16th century At the beginning of the 16th century, Kiev was at the centre of the Muscovite–Lithuanian Wars. The growing threat from the Ottoman Empire in the first half of the 16th century led to intensive construction work to fortify Kyiv Castle. In 1508, the Glinski rebellion happened. In June 1508, the opportunistic nobleman Michael Glinski from Turov, who had defected to Muscovy, called on the Kievan boyars to revive the Principality of Kiev under the suzerainty of Vasili III. But he was defeated in the by grand hetman Konstanty Ostrogski of Lithuania.
In 1569, on the basis of the Union of Lublin, Kiev and the Kiev Voivodeship were transferred from the Grand Duchy of Lithuania to the Crown of the Kingdom of Poland.
From 1559 to 1608, Konstanty Wasyl Ostrogski, one of the wealthiest and most influential magnates of the Grand Duchy of Lithuania in the Polish-Lithuanian Commonwealth, was the voivode of Kyiv. He had great authority among the Orthodox Christians and in the 1560s advocated for the equal incorporation of Ruthenia into the Commonwealth. The prince founded the Ostrog Academy. However, he was unfavourable towards Kiev and ignored the Sejm's orders to fortify the Kyiv Castle. This was probably due to the independence of the Kievan townspeople, who enjoyed Magdeburg rights.
In 1571–1572, a plague epidemic raged in Kiev.
In 1593, during the Kosiński uprising, Kiev was briefly captured by the Zaporizhian Cossack rebels of Krzysztof Kosiński, but the forces of Ostrogski soon retook the city.
In 1595/6, with the Union of Brest, the Orthodox Metropolis of Kiev, Galicia and all Rus' entered into union with the Roman Catholic Church during the time of Metropolitan Michael Rohoza. This established the Ruthenian Uniate Church, and in it, the new Metropolis of Kiev, Galicia and all Ruthenia, which would last until the Partitions at the end of the 18th century.
In 1596, Kiev was again briefly captured by Cossack rebels during the Nalyvaiko Uprising.
17th century In 1615, Orthodox citizens of Kiev founded the , which opened the Brotherhood Monastery and the .
In 1620, a new Orthodox Metropolis of Kiev, Galicia and all Rus' (1620–1686) was created. The Brotherhood received from the Patriarch of Constantinople the status of a self-governing unit (stauropegion), independent of the Metropolitan of Kiev.
In 1632, the Orthodox Kyiv-Mohyla Academy was founded, modelled on Jesuit educational institutions.
The townspeople of Kiev were involved in the Cossack wars led by Taras Triasylo in 1630 and Pavlo But in 1637–1638.
In 1649, Kiev was captured by Cossack troops during the Khmelnytsky Uprising. Bohdan Khmelnytsky made a triumphant entry into the city to the cheers of the Kyiv residents and Orthodox clergy. Kyiv became the centre of the Cossack Kyiv Regiment and Hundred. In May 1649, the Cossacks carried out a brutal three-day pogrom of the nobility, Catholic clergy, monasteries and churches. The pogrom was provoked by a townsman named Polegenkyi from Khmelnytsky's entourage.
On 4 August 1651, Kyiv was captured by the troops of Lithuanian Hetman Janusz Radziwiłł (1612–1655), who burned down Podil (the Lower City). The Lithuanian troops withdrew from Kyiv after a one-month occupation due to an outbreak of plague, which caused heavy losses. However, the city returned under the Polish–Lithuanian control as a result of Bila Tserkva Treaty.
On 4 June 1652, one of the Cossacks who was sympathetic to Adam Kysil secretly informed the voivode about the defeat of the crown army at Batih, advising him to leave Kyiv quickly, which he did immediately that night. The nobles, who learned of this, hastily left the city. Those who did not manage to leave by noon were not allowed to leave the city. Kyiv was returned to the Cossacks.