Background: The economic crisis disrupted traditional models based on market mechanisms and state funding, allowing the proliferation of alternative forms of cooperation that could respond to new social needs. Over the years, public-private partnership, in its various forms, has become strategically important in areas where, in the past, only public companies operated. In particular, management experiments aimed at introducing project financing in the management of public health authorities have been activated. Aim: The purpose of this research was to analyze the effectiveness of public-private partnership in healthcare in order to examine strengths and weaknesses and to highlight best practices adopted. Methodology: To pursue the research objectives the multiple case study methodology was chosen. The cases were developed through information collected by literature review; desk analysis of documentation provided by corporate managements and private partners and by conducting semi-structured interviews with actors involved in decision-making processes. Interviews were conducted with the general manager, the medical director and the project manager (RUP) of both public health companies. In the private companies, the chief operating officer was interviewed as the coordinator of the project financing. Results: The analysis of the projects revealed very different management models. The present analysis made it possible to highlight the main critical issues of project financing: information asymmetry, inadequacy of specific skills and extreme profit orientation. Through the analysis it was also possible to identify the strategic choices that permitted to achieve better results from a social, economic and financial point of view. Conclusions: The evidence collected will enable to make more effective and efficient choices in the design of future projects between private subjects and public authorities.