Since the mid-1990s, Italy has made significant steps towards federalism, decentralizing political, fiscal and administrative powers, also by means of a major constitutional reform. Yet, 20 years after the beginning of this process, the country is experiencing problems in finalizing these reforms towards a stable federal architecture. This article examines Italy as a case of failed federalization. Adopting a long-term focus inspired by the 'gradual institutional change' approach, we argue that federalization has been trapped between a rather anomalous (and pathological) alliance between a persistent centralism, which prevailed when Italy was born as a state in 1861, and an ever-present strong tradition of localism. This approach allows us to show the very incremental nature of institutional change and to map changes and continuities along the 150 years of the Italian state, identifying both political and cultural factors that help to explain this unfulfilled journey towards federalism.