The paper focuses on the role of the Danish viceroy of Northern Estonia in the events that led to the uprising on the night before St. Georges day in 1343 and to his activities during the uprising. The St. George’s Nights Uprising in Northern and Western Estonia (1343–1345) is usually perceived as a conflict between the native Estonians and the German-speaking elite. Even though the uprising began in an area under Danish rule, the role of the Danish viceroy in these events is hardly touched by historians.

Previous historical research has seen the dominant position of German-speaking royal vassals in Northern Estonia and their suppression of native Estonians, as well as political instability caused by the negotiations between Valdemar IV and the Teutonic Order on the sale of Northern Estonia coupled with the interest of King Magnus of Sweden and Norway towards the region as the probable reasons for the uprising.

This paper claims, that the main reason for the uprising lay in extraordinary taxation. Even though the sources are scanty, it can be said, that Konrad Preen collected extraordinary taxes in Northern Estonia on behalf of King Valdemar IV of Denmark (1340–1375) in the years 1340–1343. These extraordinary taxes were probably approved by the dominant royal vassals in hopes of persuading king Valdemar IV not to sell the region to the Teutonic Knights.  The fact that before the uprising began, a group locals sent their envoys to the king to complain of their oppression with high dues, can be considered as an attempt to persuade the king to decrease the extraordinary taxation. Therefore, the uprising must be seen as directed against the Danish king and his administration in Northern Estonia, as well as against the dominant German-speaking royal vassals of the area. Furthermore, this was definitely not a peasant-uprising. Rather it’s participants and supporters can be argued to have come from various social backgrounds united by their discontent with the Danish administration of Estonia and/or the extraordinary taxation. Then again not all those opposed to increased taxation took part in the uprising.

Viceroy Konrad Preen was taken prisoner by the Teutonic Order and released in the summer of 1344. Historians have usually dated his capture by the Teutonic Knights to some point before the beginning of the uprising. By a new analysis of the sources this paper claims that Konrad Preen was in the castle of Narva during Lent 1343 and seems to have been captured by the Order only after the uprising had begun. Probably he was taken captive in the beginning of May 1343 in the Teutonic Order’s castle of Paide during an arbitration between Danish authorities in Northern Estonia and the leaders of the uprising organized by Burchard von Dreileben, the Master of the Livonian Branch of the Teutonic Order.

There is reason to believe that the Burchard von Dreileben captured viceroy Konrad Preen in order to use the uprising to take over Northern Estonia. King Valdemar IV of Denmark was hesitant in selling the region to the Teutonic Knights, and the dominant royal vassals in the region undoubtedly opposed the sale. After the viceroy had been captured, Burchard von Dreileben set out to crush the rebellion in Danish Estonia and coerced the leading royal vassals to elect him as their provisional guardian, viceroy and protector. As a result, the order had the most important royal castles and administrative centres of Danish Estonia in their hands and king Valdemar IV finally conceded to sell the area to the Teutonic Knights.