This article focuses on Italian regional chief executives and aims to investigate if and how the Italian regionalization process has affected regional chief executives’ career trajectories. Our analysis is based on an original dataset on political careers of regional heads of government in Italy from 1970 to 2015. After presenting our two research expectations, we find that the direct election of regional presidents and the decentralization process have gone hand in hand with the selection of more regional political outsiders and visible politicians as well as with a higher integration between institutional levels in terms of career paths.