Regional cabinet members (RCMs) are key political actors in subnational politics, especially in federal systems or in countries that have undergone a process of regionalization or devolution, even though they are still less studied than federal or national ministers. Italy and its regionalization process represent an interesting case study to understand how and under what conditions members of regional cabinets can exit from politics or move upwards, or downwards the different tiers of government. By using an original dataset of 721 RCMs in ordinary statute regions we tested through multinomial regression analysis whether political and institutional or personal factors influence their movements (both legislative or executive) upward, that is, toward national and/or European positions, backward toward local (both provincial or municipal) positions or their exit from politics. Our results show that both political–institutional and individual factors matter. In particular, displaying a previous national career favors upward movements while being a technician or independent favors the exit from politics.