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In Italy, following World War II, resurging jusnaturalism put legal positivism on trial. The movement accused legal positivism of having facilitated, or even encouraged, the establishment of fascism. The sociological and realist schools also questioned positivism, though on a more epistemological than moral level, leading to further critiques. Norberto Bobbio, as a jurist and philosopher, contributed to the core of this debate. He opted to reform positivism instead of defending it dogmatically. Furthermore, the philosopher revisited some key points, while deconstructing the mechanisms underlying others. This article explores the tension experienced by legal positivism through Bobbio’s contribution, and to discuss how this doctrine inserts in a broader “historical destiny.”