The goal of the paper is to study all the implications of Donald W. Winnicott’s definition of democracy as maturity. Why is democracy the only political regime to achieve that which is the goal of human life in general: to go beyond immaturity and its dangers? How does it relate to psychological maturity in general, which human beings have to achieve by themselves in ordinary life? What are the challenges and risks implied (and revealed) by such a definition, since immaturity is a chronic and ever renewing danger in human history? This paper tries to answer these questions through a careful and internal reading of one precise Winnicott article. It allows us to set up and redefine the political frame, the human foundations, and the old and new challenges of democracy as such, which it faces today no less than before.