In the 13th century the campaigns to the shores of the Baltic were waged within the framework of the Crusading movement. The high spirit of its participants was evident, believing that they were performing a God-pleasing mission to the highest degree and conscious of themselves as an instrument of God. A constant influx of military reinforcements from Western European countries was necessary to keep the captured territory. Almost every year Bishop of Riga Albert von Buxthoeven went to Germany to recruit pilgrims. The Crusade to Livonia was of a permanent nature: Northern Crusaders arrived in Livonia every year, albeit in different numbers.
The contribution of the pilgrims was undoubtedly great, but it could not become decisive, so military contingents arriving to help the Crusaders were rarely numerous. The exception was, perhaps, only the first arrival of Bishop Albert in Livonia, when he was followed by about 2,300 pilgrims, and the expedition of the Duke Albert I of Saxony in 1219 (note: "pilgrims" should be understood as the secular volunteers involved in the campaigns in the Baltics; they also were called "guest knights"). About 300 to 1,000 pilgrims came at any one time, which was clearly insufficient for the Christianization of the Baltics. Regrets in this regard can be found in The Livonian Chronicle of Henry. Thus, Henry of Latvia reported that in 1201 the Bishop returned to Livonia with few pilgrims whom he was able to collect, and complained in 1211 that only a few pilgrims had arrived in Livonia. In addition, the arrival of pilgrims was by no means regular, and they used to remain in Livonia, as a rule, for no more than a year. In fact, the size of the military reinforcements depended almost exclusively on the efforts of Bishop Albert. Contrary to popular belief, the then Popes did not equate the Crusades to the Holy Land with military expeditions to the Baltics. Both Innocent III and Honorius III, actively directing Western chivalry to Syria and Palestine, paid relatively little attention to Livonian affairs in general. And among the German feudal lords, it was considered more worthy to make a trip to the Holy Land than to the Baltics. This problem was partially solved by the decision of Bishop Albert to establish a military order by analogy with the Knights Templar and Hospitallers, and thus came to be the Order named The Livonian Brothers of the Sword.
Bishop Theoderich von Treyden, who was replacing the then absent Bishop Albert (who was in Germany at the time), established the Livonian Sword Brethren in 1202. This Order was to become that serious military force that the Livonian Germans needed so much.
The first mention of the Order’s participation in military actions against heathens refers to 1205, when the Sword Brothers, together with the squad of the Bishopric, defeated a Lithuanian detachment.
In the first instance the Order was few in number and it took at least two years to establish it completely. However, since 1205 the Order’s knights had been involved in the Northern Crusaders’ campaigns constantly. For instance, as early as next year, intending to organize a campaign against the Livs (Livonians), Bishop Albert, involved the Sword Brothers along with the pilgrims and his own troop. In the battle that took place near Holm town on June 4 an Order’s knight named Arnold distinguished himself attacked the enemy first. On December 26, 1207 the Sword Brothers participated in the rout of the Lithuanians at Ascheraden (Aizkraukle). In 1208 the Order’s warriors took part in the capture of Selburg (Sēlpils; Vecsēlpils).
Until 1208 the Sword Brothers fought exclusively alongside the Bishop's troops, conducting military operations only upon agreement with him. But then the situation changed. In 1208 the Crusaders and Latgalians began their combined onslaught on the Estonians. The Latgalians elders and Brother Berthold, the Order’s Komtur (Commander) in Wenden (Cēsis) Castle and the Provincial Master of Cēsis, concluded an agreement of offensive against the Estonians and launched an attack on them. Nothing is known about the participation of the Bishop in this agreement, which is not surprising: at that time Albert concentrated his main efforts on firmly consolidating his acquisitions in the areas of the Daugava (the Western Dvina), and starting another war in the north apparently was not part of his plans.
Wanting revenge for the invasion, the Estonians laid siege to the Latgalian castle called Beverīna. In need of help Beverīna’s defenders applied to the Order but not to the Bishop, considering the Sword Brothers as the most real allies. A Latgalian messenger sent to Wenden was received by not the local Komtur (Berthold of Wenden), but by the Order’s Master himself, Wenno von Rohrbach, and the next morning the Order's army, reinforced by local Latgalians, arrived to the aid of Beverīna. It is noteworthy that the Master was at the time in Wenden, but not in Riga, as usual, as well as how quickly the Sword Brothers managed to march. Obviously, the Sword Brethren’s army was already on alert. These facts indicate that the Order focused its attention on the offensive against the Estonians and mobilized its main forces to accomplish this task.
In December 1208 the Bishop had clarified his viewpoint on the war started by the Order and Latgalians. It was expressed not by the Bishop himself, who was in Germany at the time, but by Hermann, his Vogt in the areas of the Livonians. He was very indignant about the constant attacks on the Estonians, warned against excessively annoying the heathens and thus provoking them to attack against the fragile Christian faith in Livonia, and demanded peaceful negotiations. At the meeting with the Estonians it was decided to postpone the conclusion of a peace treaty until the return of the Bishop, at the same time the parties agreed to an armistice. The report of the chronicler upon the activities of Hermann and the negotiations is very vague, but, apparently, the Order also agreed to a truce with the Estonians.
Returning to Livonia in 1209, the Bishop continued his advance upstream of the Daugava and organized campaigns against Koknese and against Duke Visvaldis of Jersika. The Order did not participate in them. The campaign of the Bishop ended with the construction of Koknese castle and the recognition of vassalage with the Bishop of Riga by Duke Visvaldis.
After that, the Sword Brothers started again a war against the Estonians. Henry of Latvia pointed out that this occurred after the expiration of the truce. In the same year the combined forces of the Sword Brothers and Latgalians, led by Berthold of Wenden and a Latgalian leader called Russin, invaded Ugandi (Ungannia). That was the year when Brother Volkwin von Naumburg zu Winterstätten became the next Master of the Order after the death of Wenno von Rohrbach.
In 1210 the Sword Brothers participated in defending Riga against the Curonians. Then the army commanded by Komtur Berthold of Wenden arrived to the aid of Riga. According to Henry of Latvia, the Curonians lifted the siege just before the approach of Berthold's troops. In the same year Komtur Berthold and the Latgalians, reinforced by the vassals of the Bishop named Alexander and Siegfried, attacked the Estonians. During this campaign they captured the Odenpäh (Otepää) Fortress.
Desiring to avenge, the Estonians besieged Wenden, but the approaching army of Caupo, who was a baptized leader of the Livonians of Turaida, forced them to retreat. The allies launched a pursuit, but near the Gauja (Ümera; Imera) River were ambushed and defeated. Caupo’s son called Berthold died in that battle. The chronicler pointed out that the composition of the defeated troops were also detachments of the Bishop’s vassals called Wichmann and Alder. However, this defeat did not shock the Sword Brothers. Already in February next year, Komtur Berthold and Russin repelled the Estonian raid on Metsepol (Limbaži). Then in March Komtur Berthold was also involved in the siege of Fellin (Viljandi) Castle. In April Komtur Berthold, the Bishop's vassals and Caupo organized a raid on Sakala County. In the same year the Sword Brothers unblocked Caupo’s castle besieged by the Estonians, and during the subsequent defeat of the Estonians, a Knight-Brother called Ewerhard especially distinguished himself in battle. In addition, in 1211, the Sword Brothers along with Bishop’s squad and the Latgalians participated in the march on Sakala, Nurmekund and Ugandi.
In 1212 the Holy Roman Emperor, considering the significant contribution of the Livonian Sword Brethren to the Christianization of the Baltics, granted the Charter of on the Exclusive Possession of Sakala and Ugandi to the Sword Brothers. The Sword Brothers in their turn conceded to Bishop Albert the right of possession of the areas of the Daugava. In the same year the Lithuanians invaded the possessions the Bishopric of Riga in Lennewarden (Lielvārde) administered by the Bishop’s vassal called Daniel. Daniel of Lennewarden was not able to resist the invasion, and the Lithuanians freely raided the Bishopric’s lands until the Sword Brothers, led by Master Volkwin, wiped out almost the entire Lithuanian unit, including its leader.
In 1214 the Order’s warriors led by Master Volkwin participated in a successful march on Rotalia (Läänemaa). The following year, the Sword Brothers were among the defenders of Riga stormed by the Oeselians. The militant knights of the Livonian Sword Brethren and especially the tireless Komtur Berthold, whose name terrified enemies, more than once turned the heathens to flight just by their appearance. For example, the Estonians of Sakala and Ugandi, who besieged the Latgalian castle of Autine in 1215, had abandoned their camp and fled as soon as they find out that a detachment led by Komtur Berthold was on the move to the aid of the castle.
In 1215, the Sword Brothers significantly increased the onslaught against the Estonians. Another expedition to Ugandi was undertaken by the Sword Brothers of Wenden, and then this area was devastated nine times by the Latgalian allies for a year, after which the Estonians of Ugandi had finally recognized German domination.
In 1216, the knights of the Order marched on Rotalia, making up the main body of the Christian army, which forced the Estonians there to obey. In April, the Sword Brothers of Riga together with the troops of the Bishop strengthened the harbor of Dünamünde (Daugavgrīva), which was threatened by the Oeselians. In the same year, according to the chronicler, Bishop Albert and Master Volkwin, at the head of troops composed of the Sword Brothers and pilgrims, undertook a campaign against Harrien (Harjumaa; Harju; Rugel). Thus, this time, under the direction of the Master, there were not only members of the Order, but also pilgrims from Germany. Perhaps Master Volkwin was the Commander-in-Chief of the whole army of Christians during this campaign. This was the evidence of the increasing military prestige and credibility of the Sword Brothers, who were already acting as a kind of general staff, coordinating and heading military campaigns in Livonia. In the same year the Sword Brothers led by Komtur Berthold defeated Russian troops, which were devastating the possessions of the Latgalians.
However, the next year was extremely difficult for the Sword Brothers, as it was for all the Germans who lived in Livonia. In February 1217 a 20,000-strong army, composed of the Russian warrioirs, the Estonians from Sakala, Harrien and Oesel (Saaremaa), under the command of Prince Vladimir of Pskov and Stadtholder of Novgorod Tverdislav, invaded Ugandi. They approached Odenpäh city and besieged it. The city defended by the garrison composed of the crossbowmen of the Bishopric and the Sword Brothers was in a desperate situation. The united army of the Bishopric, the Sword Brothers led by Komtur Berthold, and the Baltic allies headed towards the city to the rescue of its besieged residents. However, the forces were still lacking: the Crusaders managed to gather only 3,000 men. Trying to unblock Odenpäh with this ratio of forces was pointless, and the Crusaders broke through into the city in order to strengthen its garrison. During a desperate battle, many knights died, including Brother Konstantin, Brother Ilias von Brünninghausen, and Komtur Berthold himself. The breakthrough was carried out, but Odenpäh still could not withstand the siege for lack of food. The Crusaders made peace on severely disadvantageous terms: they had to leave Ugandi.