As early as 393 Dionysius had attacked Rhegium on the Italian side of the strait, opposite Messene. The attack had failed, but since the non-Greek Lucanians were menacing the Greek cities in Italy anyway, many of the latter formed a defensive alliance - both against the Lucanians and against Dionysius (Diod. XIV 90-91).
In 391 Dionysius, his back guarded by the treaty with the Carthaginians, brought an army across the strait to Italy. He had apparently secured Locri Epizephyrii (just up the coast from Rhegium on the east) as an ally, so he landed there, marched on Rhegium, and besieged it. Other Greek cities in Italy (Croton and Thurii are named or implied) stood by Rhegium and sent a fleet to hinder the siege. Eventually Dioynsius was forced to retreat to Messene. He then formed an alliance with the Lucanians and, it seems, persuaded them to attack Thurii. Dionysius’ brother, Leptines, commanded the Syracusan fleet in the next year and was supposed to assist the Lucanians by sea, but after Leptines had picked up some Thurian survivors from a battle which the Thurians had lost against the Lucanians, he negotiated an armistice between the two. Dionysius, not surprisingly, relieved his brother of the command shortly thereafter (Diod. XIV 100-102).
Dionysius went on the attack again in 389. This time he laid siege to Cau-lonia, a small Achaian colony a little up the coast, on the west, from Rhegium. Another Achaian colony, Croton, sent aid to Caulonia, but Dionysius surprised and defeated those troops. In fact, he managed to capture some 10,000 prisoners whom he - for once - graciously set free. The magnanimous gesture worked, and most of the Greek cities in Italy now made peace with Dionysius. This left him free to capture Caulonia in 398 as well as, in the next year, Hipponium (a Locrian colony, opposite Caulonia, on the eastern coast). He transferred the inhabitants of both cities to Syracuse and awarded their territory to the Epiz-ephyrian Locrians. In 387 Dionysius besieged Rhegium, now bereft of allies, and after an eleven months’ siege, he took it. He allowed those Rhegines who had the money to ransom themselves, the rest he sold into slavery (Diod. XIV 103-112).
In the next few years Dionysius founded several colonies on the Adriatic Sea - Lissus and Issa on the eastern side, Ancona and Hadria on the western side. Additionally, he assisted the Parians in founding a colony on the island of Pharos (Diod. XV 13) near Issa. Dionysius also took the city of Croton (Dion. Hal. Rom. Ant., XX 7). The paucity of the evidence hinders analysis of this activity, but one may suggest two possible motives: profit from trade in the Adriatic and access to a pool of Celtic mercenaries. Dionysius had need of both. Unfortunately for him, the peace with Carthage which had allowed this tremendous expansion of his power was now fraying.
Dionysus had made alliances with some cities which the Carthaginians regarded as dependent on them, and the Carthaginians responded by making alliances with Greek towns in Italy not under Dionysius’ control. In 379 the two sides came to blows. Two battles were fought, the first at an unknown place called Cabala (a Syracusan victory) and the second at Cronium near Panormus. This time the Carthaginians won decisively and in the negotiations for peace Dionysius agreed to pay a thousand talents to the Carthaginians as well as to accept the River Halycus (midway between Selinus and Acragas on the southern coast) as a boundary between the Carthaginian and the Syracusan dominions (Diod. XV 15-17). In Italy the Carthaginians wrested Hipponium from Dionysius and gave it back to the previous inhabitants (Diod. XV 24).
The next ten years are a blank. In 368, however, Dionysius tried one last time to dislodge the Carthaginians from Sicily. He won Selinus and even captured Eryx in the northwest, but his attempt at besieging Lilybaeum failed. Additionally, the Carthaginians captured much of his fleet while it lay in Eryx’ harbor. Dionysius died that same year after ruling Syracuse for 38 years (Diod. XV 73).
As a ruler he appears never to have enjoyed popularity (Seventh Letter, Pp. 331d-332c), and frequent mutinies always kept him on his guard - he is the tyrant who in the famous story of the sword of Damocles continually sat with a sword suspended over his head by a single thread (Cicero, Tusc. V 61). An acute need for money characterizes his administration, and financing his wars must have imposed great hardships on his subjects. Yet his overall success speaks for itself. To his son, also called Dionysius, he left behind an empire which stretched from the Halycus on Sicily across the straits and into southern Italy, with outposts on the Adriatic Sea. Finally, Dionysius also fancied himself a poet. He wrote tragedies, one of which, The Ransom of Hector, even won the first prize at a festival in Athens (Diod. XV 74; Snell, TGF 76, T. 3). Too little of his poetry survives to form an opinion on its quality now, and one may doubt that ancient critics, given who Dioynsius was, judged it dispassionately. All the same, it shows another side of the tyrant; and his participating in the dramatic festivals at Athens as well as staged recitals of his poetry at Olympia (Diod. XIV 109) shows that he maintained contact, at least culturally, with mainland Greece.
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