In the war of 392-391 most of the Sicels joined the Cartha ginian leader Magon ; but he was successfully withstood at Agy rium by Agyris, the ally of Dionysius. The two tyrants drove Carthage to a peace by which she abandoned all her Sicel allies to Dionysius, who founded the towns of Hadranum and Halaesa for them. This time he took Tauromenium and settled it with his mercenaries.
Dionysius in 390-387 warred against the Italiot cities in alliance with their Lucanian enemies. Rhegium, Croton, the whole toe of the boot, were conquered. In the Adriatic he helped Hellenic extension, desiring no doubt to secure the important trade route into ceptral Europe. He planted directly and indirectly some settlements in Apulia, while Syracusan exiles founded the more famous Ancona. He helped the Parians in their settlements of Issa and Pharos; he took into his pay Illyrian warriors with Greek arms, and helped the Molossian Alcetas to win back part of his kingdom. He was even charged with plotting with his Epirot ally to plunder Delphi, and sent a fleet along the west coast of Italy, to carry off the wealth of the great temple of Caere.
In the third war (383-378) Dionysius seems for once to have had his head turned by a first success. His demand that Carthage should altogether withdraw from Sicily was met by a crushing defeat. Then came a treaty by which Carthage kept Selinus and part of the land of Acragas. Dionysius had also to pay i,000 talents. In the last years of his reign he gave help to Sparta against Thebes, sending Gaulish and Iberian mercenaries to take part in Greek warfare. His last war with Carthage, which began with an invasion of western Sicily, and which was going on at his death in 367 B.c., was ended by a peace by which the Halycus remained the boundary.
The tyranny of Dionysius fell, as usual, in the second genera tion ; but it was kept up for ten years of ter his death by the energy of Philistus, now minister of his son Dionysius the younger. It fell with the return of the exile Dion in 357.
Between the death of Dion in 354 and the coming of Timoleon in 344 we hear of a time of confusion in which Hellenic life seemed likely to die out. The cities, Greek and Sicel, were occupied by tyrants. The work of Timoleon (q.v.), whose headquarters were first at Tauromenium, then at Hadranum, was threefold—the immediate deliverance of Syracuse, the restor ation of Sicily in general to freedom and Greek life, and the de fence of the Greek cities against Carthage. The great victory of
the Crimissus in 339 led to a peace with Carthage with the old frontier ; but all Greek cities were to be free, and Carthage was to give no help to any tyrant.
During the 20 years after the death of Timoleon (336-317) the Carthaginians played off one city and party against another, and Agathocles (q.v.), following the same policy, became in 317, by treachery and massacre, undisputed tyrant of Syracuse, and spread his dominion over many other cities. Acragas, strengthened by Syracusan exiles, now stands out again as the rival of Syracuse. The Carthaginian Hamilcar won many Greek cities to the Punic alliance. Agathocles, however, with Syracuse blockaded by a Carthaginian fleet, planned to carry the war into Africa.
For more than three years (310-307) each side carried on war fare in the land of the other. Carthage was hard pressed by Agathocles, while Syracuse was no less hard pressed by Hamilcar. Agathocles won many battles and towns; he quelled mutinies of his own troops; by inviting and murdering Ophellas, lord of Cyrene, he doubled his army and brought Carthage near to de spair. Meanwhile Syracuse, all but lost, had driven back Hamil car, and had taken him prisoner in an unsuccessful attack on Euryelus, and slain him when he came again with the help of the Syracusan exile Deinocrates. Acragas, deeming Agathocles and the barbarians alike weakened, proclaimed freedom for the Sicilian cities under her own headship. But her hopes perished when Aga :chocks came back from Africa, landed at Selinus, and marched to Syracuse, taking one town after another. He now relieved Syracuse from the Carthaginian blockade; his mercen aries gained a victory over Acragas; and he sailed again for Africa; when fortune turned against him there he left his sons and his army to death, bondage or Carthaginian service, and came back to Sicily almost alone. Yet he could still gather a force which enabled him to seize Segesta, to slay or enslave the whole popula tion and to settle the city with new inhabitants. A peace with Carthage, with the old boundary, secured Agathocles in the posses sion of Syracuse and eastern Sicily (301).