Tallinn, the home city of our musem, has seen its share of different rulers throughout the ages. Before the declaration of Estonian indepencence a century ago, it witnessed the reigns of the emperors of Russia, and the kings of Sweden and Denmark. But for 215 years between 1346 and 1561, for a period longer either Russian, Swedish or Danish rule, the city of Tallinn owed fealty not to a monarch, but instead to a religious organisation, an order of warrior monks – the Teutonic Knights.

The Teutonic Order was one of the three great military orders of the Middle Ages, its two equals being the Knights Tempar and the Knights Hospitaller. They share a turbulent history of defending the Catholic realms of the Holy Land, but each made its influence felt throughout all of medieval Christendom in different ways.

This article tells the tale of the Teutonic Knights in medieval Livonia – lands that roughly correspond to today’s republics of Estonia and Latvia. We find it incredibly appropriate that our musem inhabits a house that was built in Tallinn during the era when the city ruled by the members of a military order. We would like to introduce the history of the Teutonic Knights in Estonia, so our guests could think back to those days while enjoying the collection of splendid insignia we exhibit between the walls that centuries ago witnessed the lives and actions of these men.

German minnesinger (troubadour) and poet Tannhäuser pictured in the robes of the Teutonic Order. Codex Manesse (ca 1300).
Foundations in the Holy Land

Like the other major religious military orders, the Teutonic Knights were established in the Holy Land, as a result of the crusading movement. They were the youngest of the “great three”. The pious warriors who formed a religious brotherhood in the winter of 1119–20 with the aim of protecting pilgrims travelling to the Holy Land received papal confirmation as the Knights Templar in 1129. The hospital of Saint John in Jerusalem went through a gradual transformation over the 1130s and 1140s before fully becoming the Knights Hospitaller in the 1150s. The Teutonic Order, however, only formed in the last decade of the 12th century – it was born during the Third Crusade, under the imposing walls of the fortress city of Acre.

Depiction of the Siege of Acre  in a medieval manuscript ca 1280 – Biblotheque Municipale de Lyon, Ms 828 f33r

The rule of the Catholic lords of Europe who conquered the Holy Land during the First Crusade, had begun to crumble in the Levant by that time. In 1187, the imposing Muslim ruler and general Saladin captured Jerusalem from the Christians. The loss of the Holy City unleased social and religious shock waves that resonated throughout Catholic Europe, and the Pope immediately issued a call for a great crusade. The kings of France and England were the first to take the cross, shorty followed by the Holy Roman Emperor, and many other princes and nobles.

One main target of the campaign was the city of Acre that had also fallen under Saladin’s rule. Laying siege to its mighty walls for nearly two long years (1189–91), the crusader camp suffered greatly not only from the numerous combat casualties but also from various disesases. Since the Knights Hospitaller could not care for all, some North German pilgrims allegedly sacrificed one of their ship’s sails to set up a field hospidal.

Under the patronage of the Virgin and with the support of Holy Roman Emperors, this lone hospice eventually grew into a religious organisation, the Teutonic Knights – more accurately called the Order of Brothers of the German House of Saint Mary in Jerusalem. They were officially militarised in 1198, adopting a rule based on other religious orders of knighthood.

To Prussia and Livonia

Although the Holy Land remained a primary concern for the Teutonic Knights, they became more involved in European holy warfare than the other great military orders. First, the King of Hungary invited them to fight against the pagan Cuman peoples on the eastern frontiers of his realm in 1211. The order grew ambitious there, and sought to enforce its own rule in contested lands, which resulted in the Hungarian monarch expelling the Teutonic Knights. Nevertheless, another Catholic prince soon sought their help.

In 1225, the Polish duke Conrad of Masovia asked the order to repel and subdue pagan Prussian tribes on the northern border of his domain, confirming their rights to seize lands there. During the following decades, the Teutonic Knights carved out an extensive domain in Prussia, subjugating the local peoples by force of arms. These Prussian territories eventually became the order’s main seat of power in early 14th century, by which time the knights had acquired further holdings on the east coast of the Baltic Sea, in the recently Christianised lands of Livonia.

From the end of the 12th century, the Catholic endeavour in Livonia was spearheaded by North German missionaries, who founded the city of Riga (the future capital of Latvia) as a centre of the new church province. With the aid of foreign crusaders, the territory of the young bishopric quickly extended over surrounding pagan lands.

An artist’s rendition of the Teutonic Knights fighting the Cumans. Illustration by Graham Turner, Osprey Military History Series.

Since the military pilgrims only stayed in Livonia seasonally, the Bishop of Riga also needed a permanent fighting force. As a solution, the military order of the Sword Brethren was founded in 1202, to support the local ecclasiastical overlord.

“The Sword Brethren” was actually a nickname of the order, derived from its coat of arms (above). The official name of the organisation was Brothers of the Militia of Christ in Livonia.

Over the course of the first third of the 13th century, German conquerors subjugated most of Livonia. During these holy wars, the Sword Brethren became increasingly independent, soon rivalling the power of the bishop, who was forced to cede a third of all converted lands to the order in 1207. Additionally, the King of Denmark, most powerful ruler in northern Europe at the time, also had his eye set on the eastern shores of the Baltic Sea. Ultimately, the Danish monarch conquered northern Estonia, while the rest of Livonia was subjugated by the Germans of Riga.

Not all pagan peoples of the east Baltic region surrendered to the Catholic invaders, however. The Lithuanian tribes that populated lands separating Livonia from Prussia remained adamant in their resistance, and decisevly defeated the Sword Brethren in the Battle of Saule in 1236. With its Grand Master and half of all members killed, the order never recovered from this catastrophe. At that point, the Teutonic Knights stepped in – following the Battle of Saule, they incorporated the remains of the Sword Brethren in 1237, and assumed power over the order’s Livonian holdings. A theocratic domain binding together the southern and eastern shores of the Baltic Sea was born.

The Order Becomes a Prince

As might be assumed, one of the main priorites for the Teutonic Knights from this point onward was securing control over Lithuanian lands that separated the order’s two major territories. Such efforts remained rather fruitless, however, and in 1260 the Lithuanian tribe of Samogitians inflicted a crushing defeat upon the Teutonic Knights in the Battle of Durbe. Revolts of subjugated native peoples then broke out in both Livonia and Prussia, hindering the consolidation of order’s power in the Baltic region for decades.

The expansion of the Teutonic Knights and the Sword Brethren in Prussia and Livonia in the 13th century.

By the end of the 13th century, Catholic conquerors nevertheless overpowered the Finno-Ugric and Baltic inhabitants of Livonia, and founded new German-dominated lordships in these territories: in addition to the holdings of the Teutonic Order, they established the Archbishopric of Riga, and three smaller Livonian bishoprics which were all ruled by prelates who also commanded secular power as local princes. The Teutonic Knights even made attempts to extend their influence to the lands of medieval Rus’, which led to several confrontations with the princes of Novgorod. The Russians eventually came out on top, and trade began to dominate over warfare in Livonian-Novgorodian relations.

During these holy wars, the Teutonic Knights had attained a sizable domain, and although they continued expeditions against the Lithuanians until early 15th century, the order was increasingly occupied with governing its realm. While it cemented its secular rule effectively in Prussia, the situation was quite different in Livonia, because the Bishop – and soon Archbishop – of Riga possessed the dominant position of authority in these lands, whereas the Teutonic Knights had inherited the officially dependant status that the Sword Brethren had held

Hence, the politics of medieval Livonia were dominated by a constant power struggle between the Teutonic Knights and the Archbishop of Riga, with neither side achieving a decisive victory. The order wished to bend the archbishop to its will, while the prelate maintained that it was the Teutonic Knights who owed him obedience. While this conflict was mostly a dispute of charters and symbols, often fought in papal or imperial courts, the confrontation repeatedly took a violent turn, resulting in open warfare, where both sides sought aid from the rulers of neighbouring lands, and on one occasion even the King of England.

The seal of Albert Suerbeer, first Archbishop of Livonia.

Unlike the Archbishop of Riga, the Teutonic Knights managed to extend their local domain during the later Middle Ages. After an extensive uprising in northern Estonia, the King of Denmark sold all his holdings there to the order in 1346. With this transaction, the city of Tallinn became a part of the Teutonic Knights’ realm. However, it did not officially belong to the order’s Livonian branch: local members of the order acted simply as governors, while the lands became the personal property of the Grand Master, who resided in Prussia.

The holdings of the Teutonic Knights were divided into three regions under the management of separate masters. The Grand Master ruled from Prussia, the heart of the realm. East Baltic lands were entrusted to the care of the Livonian Master, who was initally elected by the general chapter of the order, and later by members of the Livonian branch, with the confirmation of the Grand Master. In addition, the German Master governed numerous smaller properties and convents of the Teutonic Knights within the Holy Roman Empire.

A Realm of Warrior Monks

The Teutonic Knights were first and foremost members of a monastic order: they gave the vows of chastity, poverty, and obedience, which meant renouncing all worldly pleasures. They could own no personal propery or touch no woman, their everyday life was confined to a convent and strictly regulated, with frequent sessions prayer defining the passage of time.

The order was divided into the leading Knight Brothers, who had military obligations, the Priest Brothers, who cared for the members’ spiritual needs, and Servant Brothers who aided them in war or daily labour. Since the Teutonic Order was also a territorial lord, however, this monastic way of life had to be reconciled with the needs of ruling wide-ranging lands.

An artist’s rendition of the casual clothes of the members of the Teutonic Order, featuring a knight, a priest and a Serving Brother.

Under the leadership of the Livonian Master, the order’s East Baltic lands were administrated by officials – commanders (Komture) and advocates (Vögte). Commanders ruled rather large provinces, called commanderies, organised around a monastic convent, which should have ideally included twelve brothers, like the dozen apostles of Jesus. In reality, many convents were much smaller, while others – in strategic locations or simply more relevant areas – could include twice or even three times as many brothers. In addition to being military and political leaders, commanders also acted as the religious heads of these convents. Advocates were intitially governors of smaller territories, but many such offices later rose to a status similar to commanders.

In Livonia, the commanders and advocates were exclusively appointed from among Knight Brothers. The order’s priests and Servant Brothers could not hope for a career in the secular administration of the realm. For the Knight Brothers, there was a hierarchy of offices, some more desirable than others, that could form a ladder of advancement within the order. The Commander of Tallinn, for example, was a quite enticing position, that could open the way for being elected the next Livonian Master. In turn, a good stepping stone towards Tallinn was the advocate’s position in the north Estonian fortress Rakvere (Wesenberg).

Members of the Teutonic Order were not locals of Livonia or Prussia, but rather immigrants from Germany. The Livonian branch commonly attracted the minor nobility of Lower Saxony and Rheinland, and its membership notably included a great number of people from Westphalia. In the 15th century, Westphalians and Rheinlanders formed two major factions within the Teutonic Knights of Livonia, and oftentimes one candidate from either was presented to the Grand Master so he could choose which to appoint as the Livonian Master. However, by the beginning of the 16th century, brothers from Westphalia clearly dominated.

For the German lower nobility, the Teutonic Order presented an opportunity for a life worthy of one’s station, if the family inheritage could not maintain several sons. Naturally, there was also the crucial prospect of salvation after death. An ideal Knight Brother was a young nobleman in good health and trained in swordsmanship – such members were valuable in battle and since they were born to a family of the medieval elites, also suitable as a rulers of commanderies.

As professional warriors, the Teutonic Knights understandably had an integral role in the defence of Livonia. The Archbishop of Riga and other local bishops had to rely on vassals or mercenaries, but the order itself constituted a permanent military force. Hence, the main weight of the wars against Lithuanians, Russians or other enemies fell upon its shoulders. The monastic convents were located in castles, covering the land as a network of permanently garnisoned fortifications. The main strength of the Teutonic Knights was concentrated in the centre of Livonia, where it could be dispatched in any direction upon need. Ruins of their largest castles can still be seen in Estonian and Latvian inlands today.

A reconstruction of the order’s castle in Viljandi (Fellin), Estonia. This was one of the largest fortresses of the Teutonic Knights in Livonia.
A Changing Order

The Teutonic Knights had arrived to the shores of the Baltic Sea during a time of holy wars and Christianisation. Although 13th-century crusades mostly took the form of religious conquests, they were justified with the need to defend the young church provinces of Livonia and Prussia from the attacks of pagan peoples. Throughout the 14th century, the increasingly powerful and still pagan Grand Duchy of Lithuania challenged the Catholic lords of these lands, and Teutonic Knights could present themselves as a shield that protected Christendom from this foe. But everything changed with the conversion of the Lithuanian Grand Duke in 1386.

In return for the Polish crown, the Grand Duke of Lithuania accepted Christianity and converted his realm to Catholicism. This meant that the Teutonic Knights had lost their raison d’être – if there were no pagan rulers in Northeast Europe anymore, from whom was the order defending Christendom, and why should they retain the wide-ranging lands they had needed for sustaining the fight? The emissaries of united Poland-Lithuania, who still saw the order as the main political and military foe, made sure these questions resonated throughout the Catholic world.

Late medieval Livonia. Lands of the Teutonic Order are painted pink, those of the Archbishop of Riga grey. Orange, yellow and green mark other Livonian bishoprics, brown the holdings of the city of Riga.

The Teutonic Knights naturally fiercely opposed all attempts to undermine their well-established position in northern Europe. They were the uncontested masters of Prussia, and by the Late Middle Ages they often had the upper hand in conflicts with the Archbishop of Riga. In general, the internal politics of Livonia became somewhat more stable by the mid-15th century. Previously, the order and local bishops had often co-operated, but they usually nevertheless acted as independent princes. From the 1430s onwards, it became a custom that the lords of Livonia with their estates would meet in a regional diet (Landestag), to discuss acute political problems as a sort of confederacy. Teutonic Knights, as the strongest Livonian power, could hope to lead this union.

By the 15th century, the Teutonic Order itself had attained an aristocratic character that was quite different from the original religious fraternity of pious warriors. As mentioned, it offered a proper way of life for the sons of lower noblity, who brought their elite status along when joining the order. As rulers of impressive holdings, the members of the order were not so different from their lay relatives.

The Livonian Master certainly resembled a secular prince, and the way his commanders and advocates governed the land did not differ remarkably from counts or other nobles in their fiefs. The Teutonic Knights also adopted many traditions of the lay orders of chivalry (on this, see another one of our articles: https://tallinnmuseum.com/2018/08/02/interchange-of-traditions-between-religious-and-secular-orders-in-the-late-middle-ages/). Outwardly, these processes made the Teutonic Knights seem more like a secular noble fraternity, but inwardly it increased the demands for funds needed to sustain members.

Meanwhile, the economical conjuncture was not favourable to the Teutonic Knights. A large fraction of the order’s income came from the sale of grain which was grown on the large fields of their Livonan holdings, but cereal prices had declined following the great plague epidemic of the mid-14th century. Additionally, the loot gained from pillaging during the crusading expeditions against Lithuanians was no longer flowing in after the Christianisation of the Grand Duchy. In warfare, the heavy cavalry of knights as such was gradually replaced by large mercenary companies, but recruiting them cost considerable amounts of money.

The Teutonic Knights were hence in a though spot, but they certainly wanted to hold on to their Baltic lands, which were now under ideological attack. Since the Lithuanians had been Christianised, there were plans of relocating the order from northern Europe to the Mediterranean, where it could fight against the Ottoman Turks. The Livonian branch of the Teutonic Knights found a new justification for remaining where they were, however. They claimed that the Russians – schismatic adherants of the Orthodox church – threatened all of Catholic Christendom and had to be repelled. The volume of propaganda initially outweighed actual danger, but the “Russian threat”, as the order came to call it, did take form in reality over the course of the 15th century.

An artist’s rendition of the Grand Master, a Knight Brother and a half-brother (a servant with quasi-membership) ca 1420.
The “Russian threat” and the Reformation

Although the eastern frontier of Livonia also marked a religious border – or even a civilisational divide – between the Catholic and Orthodox worlds, the Germans and Russians of the region actually had a deeply intervowen and largely peaceful relationship. Novgorod and Pskov were prime trading partners for the Hanseatic merchants, and despite the occasional war, Livonia and northwest Russia formed something like a unified communication space.

An reconstructed image of the gravestone of the highly renowned Livonian Master Wolter von Plettenberg (in office 1494–1535).

After the Christianisation of Lithuania, however, the Russians were increasingly depicted as ancient foes and dangerous schismatics by the princes of Livonia. Originally largely a propaganda endeavour, the intensity of this rhetoric grew as the power of the Grand Prince of Muscovy increased. In response to the Muscovites annexing one Russian land after another – including Novgorod right behind the Livonian border – the Teutonic Order actively sought the support of Catholic Christendom against this very real enemy.

In the first years of the 16th century, a Livonian-Muscovite war finally broke out. The conflict culminated in the Battle of Smolino in September 1501 where the outnumbered troops of the Teutonic Knights and Livonian bishops, led by the “the greatest Livonian Master” Wolter von Plettenberg managed to hold the field against a stronger Russian force. Despite technically resulting in a stalemate, the battle was celebrated religiously as a great triumph in 16th-century Livonia. The war itself ended without major consequences in 1503.

The truce between Livonia and Muscovy lasted for decades – even though it was initially feared to remain short-lived, so the Teutonic Knights continued to lobby for crusading funds against Russia. But instead of a holy war on the borders of Christendom, the unity of the church itself was soon to be fractured. In 1517, Martin Luther launched the Reformation movement, which shortly had a profound effect on Teutonic Knights as well.

In 1525, the order’s Grand Master Albrecht von Hohenzollern converted to the protestant faith – and since he could certainly not head a Catholic organisation thereafter, secularised all Prussian territories of the Teutonic Knights, declaring himself the first Duke of Prussia. This meant that the order’s branch in Livonia technically became independent. The Livonian Master now officially assumed full rule over northern Estonia (which he had governed for nearly 200 years anyway), and the city of Tallinn organised grandiose celebrations for the occasion of swearing fealty to its new lord.

This new situation also meant that the Livonian branch of the Teutonic Knights now had far less support behind it, and had to manage largely on its own. But no foreign foes initially threatened the realm. The era from the 1520s to the 1550s was dominated by the Reformation, which largely prevailed among Livonian elites, even winning the hearts of many Teutonic Knights. The power struggle between the order and Archbishop of Riga also continued, frequently with the participation of prominent princes of northern Europe.

The End of the Order’s Rule in Livonia

In the 1550s, the Teutonic Knights and the Archbishop of Riga were yet again embroiled in an armed conflict, this time over the participation of the princely family of Mecklenburg in the affairs of Livonia. Although this confrontation was resolved without much bloodshed, a war of far greater proportions was on the horizon.

Ruins of the castle of Cēsis (Wenden) in Latvia. It served as a permanent residence of the Livonian Master from 1494 onwards.

By the middle of the 16th century, Mucscovy had recovered from the internal turmoil of previous decades, and its ambitious Grand Prince Ivan IV (the Terrible) had aspirations of territorial expansion. In 1554, he issued a demand for tribute to the Germans of Livonia. The order and bishops remained vague about their answer, but made no efforts to collect any necessary monies. Furthermore, although a very real threat of Russian invasion was now looming, they mostly focused on weakening each other. The Livonian-Muscovite negotiations broke down in 1557, and in the beginning of the following year, the Grand Prince declared war.

The conflict was one-sided from the beginning – massive Muscovian forces quickly overpowered and captured several strategically important castles of the order, and the Teutonic Knights were repeatedly routed on the field of battle. Within the order, these events promted the impeachement of the ruling Livonian Master, and his replacement with Gotthard Kettler, who was to become the last leader of the Teutonic Knights in Livonia.

Since the order had little hope to withstand the Muscovian attack on its own, efforts were made to plead for help from neighbouring rulers. Gotthard Kettler favoured appealing to Poland-Lithuania, and his negotiations eventually resulted in conceding the Livonian lands of the Teutonic Knights to the protection of the Polish king.

An artist’s rendition of Muscovite troops during the reign of Ivan IV.

In effect, this soon meant the disbandment of the Teutonic Order in Livonia. Its members became laymen, and Kettler was rewarded with the position of the Duke of Curonia, as a vassal of the King of Poland. Only the city of Tallinn and the north Estonian vassals of the Teutonic Knights, who had held remarkable privileges and autonomy already under the rule of the King of Denmark, protested this development, and turned to Sweden for aid. In the summer of 1561, a fleet of Swedish warships arrived to the Gulf of Tallinn, and the city renounced its loyalty to the disintegrating Teutonic Order, instead swearing fealty to the King of Sweden.

Toompea Castle in Tallinn used to be the seat of the a commander of the Teutonic Order. Nowadays, the Estonian parliament is located there.

The 324-year history of the Teutonic Knights in medieval Livonia came to an end in 1561. Although the order exists to this day, as a charitable religious organisation now based in Vienna, it lost its last extensive domain in mid-16th century. The mark it left on the Estonian and Latvian lands, once conquered under the sign of the cross, has regardless lasted throughout the ages. The Teutonic Knights were instrumental in integrating the eastern Baltic coast to medieval Catholic Christendom and to the European world.

Although the local peoples, who founded independent nation states on the lands where the order used to rule, have often condemned the violent subjugation of their homelands, many literal foundations for today’s political symbols were laid by the Teutonic Knights. The building of the Estonian parliament is located on the very site where the castle of the Commander of Tallinn stood in the Middle Ages, and each morning the national flag is ceremonially hoisted to the top of the imposing tower above it – Tall Hermann, built by the Teutonic Order in the 14th century.