This paper resumes and completes the understudied topic of the relations among Carthaginians, Italiotes and Italics between the fourth and the third century B.C. The used sources show that the existing relations of “philia”, “emporia” and “xenologia” with the cities and the peoples of ‘Megale Hellas’, which has already begun at the time of Dionysius I and Dionysius II of Syracuse, were further strengthened in the second half of the fourth century; they influenced the military strategy of the “basileus” Agathocles against Brettians in an anti–Punic way. Some sourse also show that the relationship with Carthage still existed at the time of Pyrrhus military expedition in Italy and Sicily; this intervention had not only resulted in a closer link between the Romans and the Carthaginians, but it led, in an unforeseeable way, to an inevitable military encounter.