This article examines the role of the high bailiff. This official, appointed by the sovereign, played an important part in both the public life and military affairs of the County of Flanders’ castellanies. More specifically, it focuses on the high bailiff of the Land of Waas. The aim of this contribution is twofold. Firstly, it aims to delineate what the high bailiff’s position in the castellany was, what his powers were, and whether either changed during the course of the two centuries covered in this study. Secondly, this article will examine some individual aspects of the successive holders of this office, including their family networks, career development and the status that they enjoyed. Based on these findings, conclusions will then be drawn regarding the evolving social profile of the high bailiffs of the Land of Waas.