This paper is a contribution to the study of the four classical Italian pragmatists: Papini, Prezzolini, Vailati and Calderoni. They are seen more as representatives of a pragmatist movement than as singular systematic thinkers. The center of Italian pragmatism was the periodical, Leonardo, where these authors discussed and presented an original and provocative understanding of pragmatist philosophy. Thier understanding of pragmatist philosophy has often been underestimated by the subsequent literature. They showed a good comprehension of the novelty brought by American pragmatism but, ignoring some of the most important epistemic aspects of Peirce’s and James’s theories, their philosophical proposals often missed consistency. However, even in their misunderstandings, they signaled a need and possibly a weakness of the whole pragmatist movement. Italian pragmatists underlined the importance of the concreteness of individuals in the realization of universal laws of mathematics and logic, physics and psychology. But, this attitude suffered from some serious tensions between metaphysical assumptions and methodological claims.