In this article, we examine the first volume of the correspondence between Croce and Gentile, the most important Italian philosophers of the 20th century. This volume was published in Turin in 2014. The author analyzes the strenghts and weaknesses of this edition by emphasizing that just in the letters emerges the first considerable contrast between the two great thinkers. It is the dispute about the review of Windelband on which Gennaro Sasso, Girolamo Cotroneo and Francesca Rizzo have focused during the years. At the end of the dispute Gentile comes to one of the cornerstones of his thinking: the perfect identity between philosophy and history of philosophy. Nonetheless, it must be recognised that the constant exchange of letters with the younger friend made Croce feel the need to overcome the level of erudition and historiography towards a speculative framework of the 20th-century crisis. Also starting from this correspondence one can finally understand that compared to others the Italian tradition is more suitable to think about life philosophically