The establishment of the Scottish Parliament created new institutions and a political environment which has had lasting implications for Scottish and UK politics, including furthering the rise of the Scottish National Party and the independence question. One central element of this new terrain has been the emergence of the Scottish government and the post of First Minister of Scotland. The latter, the most prominent devolved political position in Scotland, has so far been subjected to little detailed analysis. Drawing on a wide array of material, research and interviews with key individuals, this article explores four aspects: first, the nature of the office of first minister; second, how it has evolved over the past quarter century; third, what various post‐holders have brought to the role; and finally, how they have been influenced by wider contextual factors such as the changing dynamics of party support, electoral competition and intra‐party considerations. The article offers some provisional conclusions about the changing nature of political leadership and the interplay between institutional factors, public opinion and the role of the individual political actors in the twenty‐first century, which has relevance not just for Scotland but further afield.