In this article, the authors offer a critical perspective on the main tax and fiscal policy measures introduced by Italy in response to the coronavirus disease 2019 (COVID-19) crisis. The article shows that the tax and fiscal policy measures enacted thus far by Italy are short-viewed, being narrowly addressed at cushioning the effects of the COVID-19 crisis without a long-term vision of how the tax system can be thoughtfully reshaped. If the current crisis is to be intended both as a challenge and an opportunity, the authors submit that a new deal is needed, including a comprehensive overhaul of the country’s tax system.