Mission of Kostiantyn Ostrozky

On August 30, 1481, in Vilnius, leaders of a conspiracy against the Grand Duke of Lithuania and Ruthenia, Casimir IV, were executed. Among those executed was the unsuccessful claimant to the throne - Mykhailo Olelkovych, brother of the last Kyivan ruler, Semen Olelkovych. The contemporary chronicler, deeply affected by the verdict, sadly noted that it was with the death of Mykhailo that "the rule of princes" in the former capital of Rus ceased. However, this was in the capital, not in Ukraine overall.

Punishing the conspirators, Casimir IV was convinced that he was strengthening his state and preventing attempts to separate certain lands from it, especially Ukrainian ones. However, it turned out that territories deprived of their ancient rulers needed protection from enemies. Yet, he simply lacked the necessary forces and resources.

Photo: Casimir IV. Source: Wikipedia.

Moreover, Casimir IV made an unsuccessful bid in the struggle for the Crimean Khanate. In the local strife, he supported the elder sons of the founding Khan Haji Giray, while the younger, Mengli Giray, triumphed. In response, in 1482, Mengli Giray captured and burned Kyiv - along with the castle that had withstood previous sieges. Even the voivode Ivan Khodkevych fell into captivity.

Since then, the raids by the Crimean Tatars became regular. However, Casimir IV could not maintain a permanent army on the borders of his state. Therefore, Ukrainians had to defend themselves, willingly or unwillingly. For this purpose, they began to gather groups of free men - Cossacks (from Turkic languages, the word translates as "free").

Photo: The prototype of the "Cossack Mamay" was Prince Bohdan Hlynskyi, who was among the first to create Cossack units. Source: Wikipedia.

To manage these groups and the defense of the region as a whole, the most influential local princes took charge alongside officials appointed from Vilnius. Kyiv, understandably, continued to be governed by voivodes. But in Hlynsk, Vyshnivets, Ostroh, Slutsk, the rulers were specifically princes – Slutsk, among others, remained to the descendants of the executed Mykhailo Olelkovych. Other rulers also traced their lineage not far from monarchs. The Hlynskyi family, for instance, descended from the beylerbey of the Golden Horde, Mamai, the Vyshnivetskyi belonged to the Gediminids, and the Ostroh family - the Rurikids (at least, according to their family genealogy).

Photo: Ostroh - the "nest" of the Ostroh princes. Source: Wikipedia.

The Ostroh family was both the wealthiest among their "colleagues" and the most influential. And Prince Kostiantyn was also known as a talented military commander. Casimir IV passed away in 1492, but his sons - the Grand Duke of Lithuania, Alexander, and the Polish King, John Albert - witnessed Kostiantyn's victory over the Crimean Tatars near Ochakiv in 1497. It was after this victory that Ostrozky was appointed as the Grand Hetman - the chief commander of the entire army of the Grand Duchy of Lithuania. In fact, this position was created specifically for him.

"Threat from the East"

However, Lithuania's main threat awaited from the east, where the Principality of Moscow was rapidly gaining strength. Casimir IV did not display the necessary foresight here either. He concluded an "Eternal Peace" treaty with its ruler Vasili II the Dark and hoped to conduct affairs as usual. While Vilnius hoped for agreements, Moscow did not consider itself bound by any conditions. Vasili II's son, Ivan III, known as Ivan the Hunchback (later Russian historians preferred the more euphonious "the Great"), captured Novgorod, annexed Tver (which was under the protection of Casimir IV by treaty), and began to persuade the minor rulers of the Lithuanian border regions to join his side.

Photo: Ivan III. Source: Wikipedia.

Reasons for encroaching on the neighbors' individual lands were not sought for long. They recalled "ancient privileges" of defector princes, defended the "Russian" uniqueness, and spoke of the "needs of the Orthodox." Meanwhile, when the Moscow church was detached from the authority of the Constantinople Patriarch (declared "insufficiently Orthodox") and subordinated directly to the ruler, it facilitated manipulations – at times, the inhabitants of the neighboring state were called co-religionists to protect, while at other times, they were accused of heresy and unacceptable closeness to Catholics.

However, Ivan III refrained from a massive invasion for a while because he hoped to find allies in the West. Initially, Hungary seemed to be such an ally. But the local king, Matthias, passed away soon after. Then the Grand Duke proposed offering Hungary itself... to the German emperor. That is, if the latter, of course, agreed to recognize Lithuania and Rus' under Moscow's authority (this was more than three hundred years before the Molotov-Ribbentrop Pact).

Photo: Olena Ivanivna. Source: Wikipedia.

There were quite a few direct agents of the Moscow prince among the Lithuanian elite. Moreover, Ivan III forced a marriage between the Grand Duke Alexander (who lacked firmness of character) and his daughter Olena, whom he hoped to turn almost into his envoy in Vilnius.

An Invasion They Were Unprepared For

Finally, when the Moscow ruler decided that Lithuania was weakened to the "desired level," he dared to make a decisive strike. Initially, at his persistent request, Mengli Giray demanded Kyiv and Cherkasy from Alexander. Then the rulers of Novhorod-Siverskyi and Chernihiv declared their separation from Lithuania and transitioned under Moscow's rule—along with the granted lands (even though Chernihiv fell under the conspirator's control just a year before these events). Ivan III immediately took the rebels "under his protection" and in the spring of 1500... no, not a "special military operation," but outright war.

Photo: Alexander. Source: Wikipedia.

Lithuania indeed found itself unprepared for the conflict. Support from European allies, even from fraternal Poland (literally led by Alexander's brother, Jan Olbracht), if there was any, was purely moral. The army was hastily summoned, and the gathered units were sufficient to cover only one direction. The south was left defenseless. It's no wonder that the Muscovites were soon in Chernihiv.

Photo: Jan Olbracht. Source: Wikipedia.

In the north, things weren't going as smoothly for the attackers. Yet, they still had a numerical advantage. Nevertheless, Kostiantyn Ostrozky – as the Grand Hetman leading the army – dared to attack the Muscovites on the banks of the Vedrosha River. The prince even managed to crush the first ranks of the opponents, but there wasn't enough strength for further breakthrough. The enemy brought reserves into battle and turned the tide in their favor. Most of the Lithuanian army perished, and the smaller part, along with the commander and voivodes, fell into captivity.

Photo: Kostiantyn Ostrozky. Source: Wikipedia.

With no more resources for maneuvering war, the Lithuanians had to resort to a staunch defense, taking cover behind the walls of Smolensk and other fortresses. The following year, Livonia entered the war, but it quickly had to switch to positional fighting. In 1503, Alexander was forced to sign the so-called "Annunciation Truce" and practically acknowledge Ivan III's occupation of a third of his state.

Across the Frontline

According to the terms of the truce, the victors released all prisoners, except... Kostiantyn Ostrozky. The Moscow ruler recognized his military talent and sought to enlist him into service. However, the prince rejected the offer and even attempted to escape, albeit unsuccessfully. Ivan III passed away without achieving his goal. His son and successor, Vasily III, began threatening the captive with death, and he... agreed.

Photo: Kostiantyn Ostrozky in Moscow captivity. Source: Wikipedia.

What prompted Prince Ostrozky to change his mind? Historians still disagree. However, it is quite likely that he learned that there was a change in power in Lithuania, and a much more resolute and warlike Sigismund I ascended the throne. The new monarch reconciled with Crimea, which recognized his authority not only over Rus but also over Ryazan, Pskov, and even the annexed Novgorod under Moscow. It became clear that a new war was looming, and before it began, Ostrozky needed to return home at any cost. After all, the Muscovites had already broken their word several times—why wouldn't the prince resort to military stratagems?

Photo: Sigismund I. Source: Wikipedia.

As it turned out, Ostrozky was indeed brought back from exile. He was even appointed as a commander. He went to inspect the army allocated to him, curiously near the very border, and then swiftly crossed that border "to his own." Sigismund I greeted the fugitive with open arms, restored all his rights and privileges, and reinstated him as the Grand Hetman.

Photo: Mikhail Gliński's Seal. Source: Wikipedia.

The ruler's interest was evident. At this time, a new conspiracy erupted in Lithuania led by the ambitious yet unscrupulous Mikhail Gliński, who considered himself underestimated at court. The conspiracy was dangerous in itself and also because the rebels drew Crimeans to their side, and they renewed their incursions into Ukrainian lands. Eventually, Gliński switched to Vasili III's side, thereby provoking yet another war with Muscovy. This time, it turned out to be more successful for Lithuania. Ostrozky distinguished himself in it by defeating Gliński's Crimean allies and "scaring off" the Muscovites, as the prince approached the border fortresses, causing them to hastily retreat.

War Anew

However, Vasili III had no intention of restraining himself. In 1510, he captured Pskov, following his father's example by taking the city's great bell and three hundred of its most esteemed families, giving their lands and property to Moscow's "servile people." Most of the citizens of Pskov saw the loss of independence as a harbinger of the "end of the world," but there were those who praised the new ruler—such as the monk Philotheus, who declared Moscow the "Third Rome" in his letters.

Photo: Vasili III. Source: Wikipedia.

Inspired by his success, the Moscow prince decided once again to go to war against Lithuania. The first blow was again struck by Mengli Giray. However, in the battle near Vishnevets, Ostrozky managed to gain the upper hand over the Crimeans. An attempt by the Muscovites to raid Kyiv also failed. Nevertheless, this time they focused their main forces on the siege of Smolensk—three sieges in a row, the last of which resulted in the city's capture.

Photo: Siege of Smolensk by the Muscovites. Source: Wikipedia.

It was a very alarming signal. Many thought that Vasili III could surpass his father and eventually conquer all of Lithuania. And after that—move further west. Prince Kostiantyn understood the threat perhaps better than anyone—years of captivity had made him well acquainted with the enemy's habits.

Ostrozky analyzed the experience of the "unfortunate war" of 1500-1503. And it seems he drew conclusions. Moreover, Lithuania was not alone now. They made peace with Crimea and even persuaded Mengli Giray to switch sides. The time gained by the heroic defenders of Smolensk was used to accumulate and organize forces. The army assembled by the prince in Minsk included not only Lithuanian, Ukrainian, and Belarusian soldiers but also Poles (famous Hussars), Tatars, Germans, and Hungarians. Essentially, it was a pan-European army.

Victory of the Century

Ostrozky's genius lay in daring to "replay" the battle at Vedrosha in the decisive battle at Orsha. The Muscovites were astonished to see the Lithuanian commander step by step reproducing the same tactical scheme—and as if enchanted, they repeated their own actions from eleven years ago. Unaware that they were falling into a trap set by the prince. Or perhaps they realized it, but it was too late.

Photo: Battle of Orsha. Source: Wikipedia.

At one point, the Muscovites even thought victory was within their grasp—only to find themselves under crossfire from Lithuanian artillery and subsequent reserve attacks. Disoriented, they began to flee, but the Hussars pursued and decimated them. Most of the enemy perished while attempting to cross the Kropyvna River, which lay behind them. The casualties were so high that the river overflowed.

It was indeed a staggering rout. Although Ostrozky couldn't free Smolensk, and the war persisted for another eight years, the Battle of Orsha became the most resplendent success of Lithuanian (and thus Belarusian and Ukrainian) arms in the 16th century. Sigismund I arranged triumphs for the victorious prince in Vilnius and Warsaw, ensuring not only his subjects but also neighbors across the continent heard of the victory. Panegyrics issued in Latin and German likened Ostrozky to both Hannibal and Scipio at once.

Photo: Sigismund I, Bona Sforza, and courtiers. Source: Wikipedia.

These measures were not in vain. European rulers no longer viewed an alliance with Moscow as a "beneficial match." Even Emperor Maximilian reoriented. Before Orsha, he eagerly corresponded with Vasili III, considering him almost an equal. But afterward, he attempted to foster a relationship with Sigismund I, even arranging his marriage to his relative Bona Sforza.

Photo: Tombstone of Kostiantyn Ostrozky. Source: Wikipedia.

Yet, of course, it wasn't solely about political circumstances. The Orsha rout had far-reaching consequences. As we now know, Moscow's westward expansion was halted for a whole 150 years—until the Khmelnytsky Uprising itself. Within a century under the rule of Lithuanian princes and Polish kings, even Smolensk and Chernihiv were reclaimed. The experience of this shared victory brought the peoples of Eastern Europe closer, laying the foundations for the future Polish-Lithuanian Commonwealth. It's no coincidence that in the 21st century, a joint Ukrainian-Polish-Lithuanian battalion bears Kostiantyn Ostrozky's name. The prince's tombstone, once situated in the Dormition Cathedral of the Pechersk Lavra and destroyed during the Second World War, has now been restored through the joint efforts of Ukrainians and Lithuanians.