Dion, Aristomache's brother, at first found an honourable reception for his sister's sake; but his own worth and parts soon procured him a nearer place in his brother-in-law's affection, who, among other favours, gave special command to his treasurers to furnish Dion with whatever money he demanded, only telling him on the same day what they had delivered out. Now, though Dion was before reputed a person of lofty character, of a noble mind, and daring courage, yet these excellent qualifications all received a great development from the happy chance which conducted Plato into Sicily; not assuredly by any human device or calculation, but some supernatural power, designing that this remote cause should hereafter occasion the recovery of the Sicilians' lost liberty and the subversion of the tyrannical government, brought the philosopher out of Italy to Syracuse, and made acquaintance between him and Dion. Dion was, indeed, at this time extremely young in years, but of all the scholars that attended Plato he was the quickest and aptest to learn, and the most prompt and eager to practise, the lessons of virtue, as Plato himself reports of him and his own actions sufficiently testify. For though he had been bred up under a tyrant in habits of submission, accustomed to a life on the one hand of servility and intimidation, and yet on the other of vulgar display and luxury, the mistaken happiness of people that knew no better thing than pleasure and self-indulgence, yet, at the first taste of reason and a philosophy that demands obedience to virtue, his soul was set in a flame, and in the simple innocence of youth, concluding, from his own disposition, that the same reason would work the same effects upon Dionysius, he made it his business, and at length obtained the favour of him, at a leisure hour, to hear Plato.
At this their meeting, the subject-matter of their discourse in general was human virtue, but, more particularly, they disputed concerning fortitude, which Plato proved tyrants, of all men, had the least pretence to; and thence proceeding to treat of justice, asserted the happy estate of the just and the miserable condition of the unjust; arguments which Dionysius would not hear out, but, feeling himself, as it were, convicted by his words, and much displeased to see the rest of the auditors full of admiration for the speaker and captivated with his doctrine, at last, exceedingly exasperated, he asked the philosopher in a rage, what business he had in Sicily. To which Plato answered, "I came to seek a virtuous man." "It seems, then," replied Dionysius, "you have lost your labour." Dion, supposing that this was all, and that nothing further could come of his anger, at Plato's request, conveyed him aboard a galley, which was conveying Pollis, the Spartan, into Greece. But Dionysius privately dealt with Pollis, by all means to kill Plato in the voyage; if not, to be sure to sell him for a slave: he would, of course, take no harm of it, being the same just man as before; he would enjoy that happiness, though he lost his liberty. Pollis, therefore, it is stated, carried Plato to Aegina, and there sold him; the, Aeginetans, then at war with Athens, having made a decree that whatever Athenian was taken on their coasts should forthwith be exposed to sale. Notwithstanding, Dion was not in less favour and credit with Dionysius than formerly, but was intrusted with the most considerable employments, and sent on important embassies to Carthage, in the management of which he gained very great reputation. Besides, the usurper bore with the liberty he took to speak his mind freely, he being the only man who, upon any occasion, durst boldly say what he thought, as, for example, in the rebuke he gave him about Gelon.
Dionysius was ridiculing Gelon's government, and, alluding to his name, said he had been the laughingstock of Sicily. While others seemed to admire and applaud the quibble, Dion very warmly replied, "Nevertheless, it is certain that you are sole governor here, because you were trusted for Gelon's sake; but for your sake no man will ever hereafter be trusted again." For, indeed, Gelon had made a monarchy appear the best, whereas Dionysius had convinced men that it was the worst of governments.
Dionysius had three children by Doris, and by Aristomache four, two of which were daughters, Sophrosyne and Arete. Sophrosyne was married to his son Dionysius; Arete, to his brother Thearides, after whose death Dion received his niece Arete to wife. Now when Dionysius was sick and like to die, Dion endeavoured to speak with him in behalf of the children he had by Aristomache, but was still prevented by the physicians, who wanted to ingratiate themselves with the next successor, who also, as Timaeus reports, gave him a sleeping potion which he asked for, which produced an insensibility only followed by his death.
Nevertheless, at the first council which the young Dionysius held with his friends, Dion discoursed so well of the present state of affairs that he made all the rest appear in their politics but children, and in their votes rather slaves than counsellors, who timorously and disingenuously advised what would please the young man, rather than what would advance his interest. But that which startled them most was the proposal he made to avert the imminent danger they feared of a war with the Carthaginians, undertaking, if Dionysius wanted peace, to sail immediately over into Africa, and conclude it there upon honourable terms; but, if he rather preferred war, then he would fit out and maintain at his own cost and charges fifty galleys ready for the service.