The so-called Seventh Letter of Plato deals with Plato's attempts in the 360s to educate the young Dionysius II. If genuine, the letter is of incalculable value both historically and autobiographically. Even if forged, it is still valuable historically since it was apparently written close to the events which it describes. The argument is complicated (and here omitted), but the historian Ephorus, who cannot have been writing later than the 330s, already knew the Seventh Letter.
Plato, like most aristocrats, nursed an abiding distrust of democracy. After all, the restored democracy in Athens had in 399 executed his teacher Socrates. Plato's tract, the Apology, gives a moving version of Socrates' defense which among other things makes the democracy appear brutal and capricious for executing so wise and noble a man. In his best-known dialogue, the Republic, Plato designs an ideal state - a monarchy with a philosopher-king as its ruler. In one passage he reflects on the possibility of such a ruler existing in reality: either a philosopher would have to become a ruler or "by some divine inspiration a true love of true philosophy might arise either in one of the current dynasts or kings or in one of their sons" (Rep. 499b).
In the Seventh Letter Plato's undertaking to educate Dionysius II is justified as follows:
If ever anyone were to make the attempt to achieve the things which I had in mind regarding laws and constitutions, the time to try was now: for I would sufficiently accomplish all good things if I won over one single man. . . Mostly I was ashamed lest I should appear to myself to be Just a theorist and unwilling to set my hand to any deed. (Seventh Letter, 328b-c).
In 366 Plato came to Syracuse and attempted to win Dionysius II over. Unfortunately for Plato, Dionysius II was not exactly an apt pupil and the Seventh Letter recounts Plato's disappointment at Dionysius II's inability to comprehend philosophy. Moreover, Dio and Plato esteemed each other highly, and this grated on Dionysius II who was quarreling with Dio. Plato left Dionysius II on bad terms and returned to Athens after about a year. In 361, however, Dionysius II invited him back, and Plato journeyed to Syracuse again to make one last attempt. It met with the same success as the first, and Plato was lucky to escape with his life.
Adriatic and Italy with foundations of colonies in Apulia and with a war against the Lucanians (Diod. XVI 5 and 10). None other than Plato helped him form ties with the philosopher and politician Archytas of Taras (Plut. Dio, 18).
If Dionysius II had let his exiled uncle Dio live out his days abroad in peace, his rule might have continued longer. Instead, Dionysius II confiscated Dio’s
Estate and even forced Dio’s wife, who had remained in Syracuse, to marry another man (Plut. Dio, 18-19 and 21). Provoked beyond endurance, Dio decided to make his own play for power.
He returned to Sicily in 357 with a handful of mercenaries and landed on the southern coast, to the west of the River Halycus. He collected supporters as he marched towards Syracuse. Fortunately for him, Dionsysius II was away with the fleet in Italy, so when Dio entered Syracuse, he easily gained control of the city, except for the heavily fortified island in the harbor (Diod. XVI 9-12; Plut. Dio, 25-29). Although fighting against Dionysius Il’s supporters on the island went on for some time, the actual issue was settled. When Dionysius II’s fleet sailed against Syracuse, a Syracusan fleet loyal to Dio defeated it (Diod. XVI 16). Dionysius II withdrew to Locri Epizephyrii in Italy, where he continued to rule as the rest of his empire fell apart (Strab. VI 1,8, p. 260).
In Syracuse Dio ruled as a tyrant, but only briefly as Callipus assassinated him in 354 (Plut. Dio, 56-58). Callipus himself was tyrant for a year (Diod. XVI 31), before Hipparinus, a son of Dionysius I’s by his second marriage, returned and seized control. Hipparinus ruled for two years (Diod. XVI 36), and his brother Nysaeus thereafter for another five or so (Plut. Tim. 1). In 346 Dionysius II decided to exploit the confused circumstances in Syracuse and returned from Locri Epizephyrii. The Epizephyrian Locrians, meanwhile, rose up against the garrison which he had left behind, and regained their independence (Strab. l. c.).
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