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Ivan III's diplomacy against Sweden did not work out well; he entered into an alliance with Denmark against Sweden in 1496 that led into a brief and inconclusive war. It was settled by a sixty-year armistice in 1508, helping Russia to focus on the Baltic through the Grand Duchy. Conflict with the Grand Duchy was endemic; in the 1480s and 1490s many Orthodox princes fled the Grand Duchy into Muscovite service, bringing strategic border lands. Ivan III tried to establish peace by marrying his daughter Elena in 1494 to Grand Duke Alexander (later king of Poland 1501), but war nevertheless broke out from 1500 to 1503, and again in 1512. The armistice that halted hostilities in 1522 established the border for the rest of the century, awarding Russia control of territories brought by defecting Orthodox princes (Novgorod Seversk, Chernigov, upper Oka) and cities won in battle, including Smolensk and Briansk.

The eminent Habsburg diplomat, Sigismund von Herberstein, came to Moscow in the 1520s to help negotiate these truces and to press Russia into anti-Turkish and anti-Polish alliances, but Herberstein accomplished nothing formal. Similarly, papal initiatives (in the late 1490s and the 1510s) failed to lure Russia into an anti- Turkish crusade.

On the coveted Volga route, throughout the late fifteenth and first half of the sixteenth century, Russia was intervening in dynastic politics in Kazan, as was the Crimean khanate. When the Crimean khanate shifted its allegiance to the Grand Duchy in 1513 (alarmed at Russia's waxing power), it became a formidable foe in raids on the southern frontier and a rival in Kazan politics. Ultimately, as detailed in Chapter 3, Russia conquered Kazan in 1552 and Astrakhan in 1556. It took the next two centuries for Russia to push defensive lines into the steppe to control nomadic raids along the Volga and from Bashkirs, Kalmyks, and Kazakhs on the Caspian steppe. Meanwhile, from the 1580s Russian military units, often following trappers, pushed across Siberia, reaching the Pacific by the end of the seventeenth century.

Less successful in the time of Ivan IV was the Livonian War (1558-81), which assembled major Baltic powers—Russia, Sweden, the Commonwealth of Poland- Lithuania (created by a union of these two states, already dynastically allied, in 1569), Denmark—to contest for Livonia (approximately modern day Estonia and Latvia). Home to the Livonian Knights, these Baltic coastal lands became vulnerable territory in 1557 when the Knights secularized their Order and accepted the suzerainty of Poland and the Grand Duchy. After early gains, Russia suffered defeats at the hands of Sweden and Poland-Lithuania; Ivan IV was forced to capitulate, requesting that the Vatican envoy, Jesuit Antonio Possevino, who had been involved in negotiations with other combatants in the war, broker peace in 1582. Terms of the Treaty of Iam Zapolskii were harsh for Russia; it yielded all its Livonian acquisitions and the Commonwealth won most of Livonia. In 1583 peace followed with Sweden, which secured Estland (modern day Estonia) and the parts of the GulfofFinland coastline from Narva to Lake Ladoga that Russia had conquered.

Russia's foreign policy in the sixteenth century was conscious and focused, undermined only in the 1560s by the chaos of the Oprichnina. The seventeenth century, however, started out with anything but controlled, intentional foreign policy. The extinction of the dynasty in 1598 set Russia on the road to the Time of Troubles. Polish private magnate armies invaded in 1604 in support of the first "pretender" to the throne; the Polish king formally declared war in 1610 after Tsar Vasilii Shuiskii (1606-10) accepted alliance with the Swedes, who sent in troops in 1609. By the time the dust settled in 1613, Russia had lost territory to both.

By the Treaty of Stolbovo with Sweden in 1617, Russia ceded yet more territory on the southern shore of the Gulf of Finland, but regained Novgorod and other inland towns that the Swedes had occupied. It proved harder to reach a lasting peace with the Commonwealth of Poland-Lithuania. The Treaty of Deulino in 1618 established a fourteen-year armistice, the Commonwealth not yielding on territory (Smolensk, the Seversk lands) or on Crown Prince Wladyslaw's claim to the Russian throne. After fourteen years, around the 1630s, Russia tried to forge an ambitious alliance against the Commonwealth with Sweden, the Crimea, and even the Ottoman empire. That effort failed, as did the subsequent war Russia launched for Smolensk in 1632; its peace treaty in 1634 won for Russia only the agreement of Wladyslaw (now King of Poland) to drop his claim to the throne, while the Commonwealth won affirmation of the territorial gains of 1618.

For the next two decades the Romanovs tried to maintain neutral relations with the Swedes and the Commonwealth, focusing on building a steppe defensive frontier against the Crimeans and keeping their vassals, the Don Cossacks, from overly antagonizing the Ottoman empire. When Don Cossacks captured the Ottoman fortress of Azov (1637), Russia ordered them to abandon it (1642), and through the rest of the century worked to limit Don Cossack raids against the Ottomans, in part by increasing Russian cash and food subventions and military control.

The second half of the seventeenth century, as noted in Chapter 3, was marked by wars catalyzed by the Cossack rebellion led by Bohdan Khmelnytsky in Ukrainian-speaking "Rus'" lands of the Commonwealth in 1648. It set off a conflagration of invasion: Russia invaded the Grand Duchy in 1654, Sweden invaded the Kingdom of Poland and Baltic coast in 1655, and Russia in turn declared war on Sweden in 1656 to seek land on the Baltic. The Russo-Swedish conflict was settled relatively quickly: by the Treaty of Cardis in 1661 Russia ceded to Sweden the Livonian territories that it had won (Dunaburg, Iur'ev/Dorpat). The Ottoman empire also got into the fray caused by Khmelnytsky, eager to retain its vassal states of Moldova and Wallachia and its new acquisition of Podolia. Russia was drawn into war with the Ottoman empire (1676-81) that ended in stalemate in the armistice of Bakhchisarai in 1681. Khmelnytsky's Cossack Hetmanate, occupying the Left Bank of the Dnieper River and Kyiv, became subject to Russian control but retained significant autonomies; Russia also accepted the move of a different group of Cossacks, the Zaporozhian Cossacks, to vassalage to the Ottomans.

Russia's major engagement in these wars was with the Commonwealth of Poland-Lithuania, and here it achieved decided success. In the armistice of Andru- sovo of 1667 the Commonwealth recognized the loss of the Hetmanate on the Left Bank and ceded a large strip of territory in the Grand Duchy (Belarus'an speaking areas), including Smolensk, Seversk, and Chernigov. Thus, Russia regained what had been lost in the Time of Troubles. This was finalized in an "Eternal Peace" in 1686, agreed to by Polish King Jan Sobieski when he was eager to draw Russia into a Holy Alliance against the Turks. Because it now considered the Ottoman empire and the Crimeans vulnerable, Russia agreed to such a move after two centuries of rejecting such requests. The resultant alliance joined the Commonwealth, Austria, Venice, and Russia; Russia played its part by attacking the Crimea in 1687 and 1689, each of which campaigns was a debacle. Peter I's campaign against Azov in 1694 (held by Russia until 1711) was a further attempt to pursue Russia's traditional goal of expansion across the steppe towards the Black Sea while honoring the alliance.