This chapter analyses the relationship between Agathokles and the Carthaginians as part of a long-term historical process and a wide-ranging pan-Mediterranean system of interaction. The Carthaginians sought to maintain a dominant situation in Sicily and prevent attacks from the eastern part of the island by keeping the Greek poleis there divided. This approach clashed with Agathokles’ priorities (as outlined in chapter 6) and with the aggressive model of engagement that had been laid down by Agathokles’ predecessors. Agathokles’ invasion of Africa was a novel expansion of earlier Sicilian leaders’ approach to war with Carthage. Various structural features—especially the disparity in the naval power of Carthage and Syracuse—made its failure nearly inevitable, but it provided the template for the conduct of both the Romans and the Carthaginians in the Punic Wars.