The National Recovery and Resilience Plan (PNRR) adopted in 2021 by the Italian government is explicitly committed to push the country towards a ‘radical ecological transition’ and sustainable development. However, the institutionalization of the paradigm of sustainable development, in Italy, is a story of a failure. The aim of this contribution is to investigate the hows and whys that may help explaining the failed institutionalization of the paradigm. By combining an ideational approach with a political system perspective, our empirical investigation analyses the initiatives promoted by Italian national governments, by covering a time span of over 20 years (1992–2020). Thick historical description and process tracing are used to provide an in-depth reconstruction of the process. Our results show that adverse combinations of factors of a cognitive, institutional and political nature have hindered the adoption of substantive policy outcomes, thus leading the institutionalization of the paradigm along a disjointed path.