Drawing on ethnographic material from Brindisi, a medium-sized city in southeast Italy, this chapter analyses the role played by the city’s heritage in the (re)construction of historical memories and their significance in contemporary power games and political projects. It examines how, by establishing links with the past, the city’s heritage is used to make “symbolic statements” that are meant to legitimise power relations and the formation of new political organisations and programmes. At the same time, the chapter looks at the controversy surrounding some historical commemorative monuments and the attempts at sidelining both their symbolic meanings for the city’s identity and history, and their national significance beyond ideological characterisation. The analysis of the symbolism of new political formations points to the relevance of the historical heritage in the construction of political representation and processes of legitimation.