The aim of this paper is to analyze the importance of Political entrepreneurs and leadership for the process leading to regional autonomy in the Nordic countries. Regional autonomy is often explained by factors deriving from the autonomous regions itself, especially ethnic distinctiveness, i.e. cultural difference in matters of language, religion or ethnicity between the autonomous region and the rest of the country. Still we can find many of the factors that are believed to be important when explaining why some regions enjoy autonomy in both autonomous and non-autonomous regions. This paper focuses on the island regions in the Nordic and Baltic countries to find out what role political groups or individual actors, so called political entrepreneurs, play (or not) in the process that lead to autonomy for the region. Both regions that enjoy regional autonomy and regions that are still integrated parts of the mainland will be included in order to analyse to what extend groups and/or individuals are important when explaining the difference in autonomy. Are groups and/or individuals important when explaining the difference in autonomy? If so, which different types of groups or individuals are needed in order to achieve the goal, in this case regional autonomy in an island context? I will argue that individual matters, but they are heavily context dependent, i.e. they are dependent on the structures in each island. I will also show the need for different kinds of entrepreneurs in the process that lead to regional autonomy for the island and in this respect the importance of leadership entrepreneurs.