The relevant historiography has largely overlooked the role of Karl Haushofer as a cultural-political actor in National Socialist-Fascist relations. From 1924 to 1944, the German geopolitician dealt extensively with Italy, with an eye to both its geopolitical role in Europe and to the political system of Benito Mussolini's regime. On behalf of Rudolf Hess, he began visiting Italy during the 1930s, aiming to overcome ideological and political misunderstandings between Rome and Berlin. He established a network of contacts with Italian scholars and politicians, passed information back to the so-called deputy Führer, and attempted to influence official German policy toward Italy. He eventually promoted the development of an Italian geopolitics, and, in so doing, achieved one of the most significant cultural-political transfers from National Socialist Germany to fascist Italy. This article analyzes the contacts between Haushofer and Italy, both his political activities and his geopolitical theories. It is a case study of a history of contradictions: a man committed to Pan-Germanist culture and to the defense of German minorities abroad, Haushofer also attempted to improve relations between Berlin and Rome. Moreover, he considered the Axis from a geopolitical point of view—as a realization of the European imperial idea—and from a trilateral perspective, i.e., he viewed Japan not only as an ally, but also as a cultural and political model. The reconstruction of Haushofer's relations with Italy is, therefore, an opportunity to rethink the antinomies, as well as the global dimension, of the National Socialist-Fascist alliance.