This chapter aims to explore the origin of the Icelandic local Government chief executive position and how the present and future role of the position is influenced by the past. The position of the chief executive is the single most important administrative position at the local government level. The legal framework has its roots in a local government system put into place in 1872 and was and still is mostly Danish in origin. However, the position of the Icelandic chief executive has developed into the special case of the Icelandic chief executive, with a complex mixture of Danish, Norwegian and Icelandic traits. The discussion begins with describing the framework of the Icelandic local government system and the origin of the chief executive position and how the development of the role has been influenced by both the Danish Mayor and the Norwegian council manager. Special focus is put on the fact that the legal framework allows for the position to be occupied by either a local politician, making him/her de facto an executive mayor or by a professional hired through a job posting into the position. This provides us with an interesting angle to discuss as the role perceptions of these very different types of administrative leaders is bound to very different. This discussion is followed by a focus on recruitment and professional advancement, age and gender in relation to role perception. The chapter concludes with a discussion on the future of the role of the Icelandic chief executive in relation to changes taking place at the Icelandic local level. The research design is comparative and longitudinal as it is based on data collected in the year 2011 and data collected in 2019.