The Rule and Statutes of the Teutonic Knights and other documents of the Teutonic Order were analyzed to track the history of the Grand Master’s office. The decisions and accomplishments of successive Grand Masters were examined to expound their role and position in the Order in the analyzed period and their influence on the power wielded by the Order in the Middle East, Prussia and European bailiwicks. The author examines changes in the role of the Grand Master’s function, other supreme offices in the Order and the shaping of relations within the Teutonic Order throughout the centuries. The transformations observed in the Rule and Statutes of the Teutonic Knights and in the Order’s activities until the 20th century throw light on the specific nature of the Grand Master’s office, the Order’s condition, the impact of external influences, internal trends (reforms), changes in the Grand Master’s powers and the role of the Grand Master’s office in the Order. The second part of the article discusses the Grand Master’s residences in Acre, Montfort, Venice, Malbork, Konigsberg, Mergentheim and, lastly, Vienna. The Grand Master’s role in each of those residences is analyzed in the light of formal requirements and historical events. The residence of the Grand Master of the Teutonic Order was transformed into the official seat of the head of the state in Prussia, whereas in the reformed Teutonic Order, the palaces in Mergentheim and Vienna retained their function of the Grand Master’s residence. Changes in the Grand Master’s role and position influenced the Order’s policies and the Teutonic Knights’ status and reputation in the international arena, in particular in Prussia.