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This paper examines the history of the island of Gotland on the Baltic Sea, as a place of deep geostrategic interest for both German merchant navies and their enemies in the 14th century. This paper will focus on the invasion of Gotland of 1398 by the German crusading state of the Teutonic Order, and particularly its implications on the world of northern European trade dominated by the German Hanseatic League. The merchants of the Gotlander city of Visby helped establish the Hanseatic League two centuries earlier, and Visby remained a relatively important German trade port for centuries after this turning point. However, this paper will argue that despite its absence from the historiography of medieval European commerce, the Teutonic Order’s invasion of Gotland accelerated the downfall of the Visby merchant community as a key player in Baltic trade; furthermore, Visby’s downfall was part of a larger shift in the structure of Northern European commerce at the time.