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After making a comparative survey of Italy’s ranking in the Fraser Institute and Heritage Foundation indexes of economic freedom, this article focuses on the parameters for levels of freedom in the system of property rights. Although Italy’s ranking is high in both indexes for the system, the authors show that, when we shift our concern from formal to substantial property rights in a neo-institutionalist perspective, the Italian system would appear to be characterised by a combination of weak protection and high transaction costs. Defining ‘liberalisation’ as the process which permits the reduction of the time individually and socially necessary to maintain public structures, the essay highlights how, in recent years, the Italian system has never experienced significant increases in the level of economic freedom. By way of example, it considers the process of law-making and the low quality of its final output, as well as the poor results of more recent attempts to simplify public procedures, attempting to explain their connections with some of the features of the Italian political system. Finally, it shows how these features can explain the correlation between lower levels of economic freedom and the diffusion of other phenomena, such as black markets, corruption and lack of confidence in the state, which would appear to be typical of the Italian case.