Riga in Latvia, 1533, Livonian Order, Walter von Plettenberg, Schilling.

Riga in Latvia, Livonian Order, Walter von Plettenberg, 1533 AD.,
AR Schilling (18 mm / 1,07 g),
Obv.: WOL-PLETT-ENB´M-A´LIV , arms of the Masters of the Livonian Order on a long cross.
Rev.: MONE•NOVA•RIGENSIS•1533• , arms of the city of Riga: cross above crossed keys.
Neumann 231, Haljak 138 ; Dav. 29 .

Walter von Plettenberg was born in Welver (in Meyerich Castle), Westphalia. He went to the fort of Narva at the age of ten. He joined Order when he was about fifteen. In 1489 he was elected to marshal of the Order (Landmarschall), in 1491 he fought successfully against the city of Riga and was elected master in 1494. That same year Moscow closed down the Hanseatic office in Novgorod and imprisoned Hanseatic merchants (most of them were Livonians) there. Livonia was drifting into war with Muscovite Russia. After negotiations in 1498 failed, Plettenberg chose to prepare for pre-emptive attack against Pskov, which was then still formally independent state, but under heavy influence of Moscow.
In 1500 Plettenberg made an alliance with Grand Duke of Lithuania, Alexander Jagiellon (the Treaty of Wenden), who was in war with Russia since 1499. He also tried to convince Pope Alexander VI to issue a crusading bull against the Russians and get some indulgence money, but his efforts were in vain. In the war with Russia (1501-1503), Plettenberg showed himself as a talented and skilled commander. His strength lay in his skillful use of heavy cavalry and artillery fire. With such tactics von Plettenberg won the battle of the Seritsa River (August 1501), where an army of Livonian Confederation of 8,000 foot and 4,000 horse defeated about two times stronger army of Russians. But without the promised help of Lithuanians Plettenberg couldn't conquer Pskov and burned only stronghold of Ostrov. During the winter of 1501–1502, Russians ravaged quite harshly on Eastern Livonia and many Livonian rulers wanted to make peace with Muscovy. But Plettenberg decided to continue war and tried to conquer Pskov one more time. But because of the support from Moscow, he was forced to retreat southwest from the city and 13 September 1502 he won Battle of Smolino with his 5,000 men about 12,000 Russians. The next day, 14 September, became the Victory Day in Livonia. In 1503 peace between Ivan III and Livonia on the terms of status quo ante bellum was concluded.
During the Protestant Reformation, Plettenberg supported the Lutherans, hoping thus to subjugate the Catholic Archbishopric of Riga to him. The province was in disarray and the master had serious difficulties in ruling the territory which remained divided between the Order, the bishoprics, and rich cities Riga, Tallinn and Tartu. In 1525 Plettenberg refused to convert himself to Lutheranism and to become a secular ruler of Livonia as the Grand Master Albert in Prussia had done. Instead he became vassal or Imperial Prince (Reichsfürst) of the Emperor Charles V, thus hoping to get direct support from the Holy Roman Empire. In the beginning of the year 1535 he died quite suddenly at the age of about 85 years.

The Livonian Order was autonomous Livonian branch of the Teutonic Order and a member of the Livonian Confederation from 1418–1561. After being defeated by Samogitians in the 1236 Battle of Schaulen (Saule), the remnants of the Livonian Brothers of the Sword were incorporated into the Teutonic Knights as the Livonian Order in 1237.
Between 1237 and 1290, the Livonian Order conquered all of Courland, Livonia, and Semigallia, but their attack on northern Russia was repelled in the Battle of Wesenberg (Rakovor) (1268). In 1346, the Order bought the rest of Estonia from King Valdemar IV of Denmark. Life within the Order's territory is described in the Chronicle of Balthasar Russow (Chronica der Provinz Lyfflandt).
The Teutonic Order fell into decline following its defeat in the Battle of Grunwald in 1410 and the secularization of its Prussian territories by Albert of Brandenburg in 1525, but the Livonian Order managed to maintain an independent existence. During the Livonian War, however, they suffered a decisive defeat by troops of Muscovite Russia in the Battle of Ergeme in 1560. The Livonian Order then sought protection from Sigismund II Augustus, the King of Poland and the Grand Duke of Lithuania, who had intervened in a war between Bishop William of Riga and the Brothers in 1557.
After coming to an agreement with Sigismund II Augustus and his representatives (especially Mikołaj "the Black" Radziwiłł), the last Livonian Master, Gotthard Kettler, secularized the Order and converted to Lutheranism. In the southern part of the Brothers' lands he created the Duchy of Courland and Semigallia for his family. Most of the remaining lands were seized by the Grand Duchy of Lithuania. The north of Estonia was taken back by Denmark and Sweden.