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.

Dionysius wondered much at his greatness of mind, and received his offer with satisfaction. But the other courtiers, thinking his generosity reflected upon them, and jealous of being lessened by his greatness, from hence took all occasions by private slanders to render him obnoxious to the young man's displeasure; as if he designed, by his power at sea, to surprise the government, and by the help of those naval forces confer the supreme authority upon his sister Aristomache's children. But, indeed, the most apparent and the strongest grounds for dislike and hostility existed already in the difference of his habits, and his reserved and separate way of living. For they, who, from the beginning by flatteries and all unworthy artifices, courted the favour and familiarity of the prince, youthful and voluptuously bred, ministered to his pleasures, and sought how to find him daily some new amours and occupy him in vain amusements, with wine or with women, and in other dissipations; by which means, the tyranny, like iron softened in the fire, seemed, indeed, to the subject, to be more moderate and gentle, and to abate somewhat of its extreme severity; the edge of it being blunted, not by the clemency, but rather the sloth and degeneracy of the sovereign, whose dissoluteness, gaining ground daily, and growing upon him, soon weakened and broke those "adamantine chains," with which his father, Dionysius, said he had left the monarchy fastened and secured. It is reported of him that, having begun a drunken debauch, he continued it ninety days without intermission; in all which time no person on business was allowed to appear, nor was any serious conversation heard at court, but drinking, singing, dancing, and buffoonery reigned there without control.

It is likely then they had little kindness for Dion, who never indulged himself in any youthful pleasure or diversion. And so his very virtues were the matter of their calumnies, and were represented under one or other plausible name as vices; they called his gravity pride, his plain-dealing self-will, the good advice he gave was all construed into reprimand, and he was censured for neglecting and scorning those in whose misdemeanours he declined to participate. And to say the truth, there was in his natural character something stately, austere, reserved, and unsociable in conversation, which made his company unpleasant and disagreeable not only to the young tyrant, whose ears had been corrupted by flatteries; many also of Dion's own intimate friends, though they loved the integrity and generosity of his temper, yet blamed his manner, and thought he treated those with whom he had to do less courteously and affably than became a man engaged in civil business. Of which Plato also afterwards wrote to him; and, as it were, prophetically advised him carefully to avoid an arbitrary temper, whose proper helpmate was a solitary life. And, indeed, at this very time, though circumstances made him so important, and in the danger of the tottering government he was recognized as the only or the ablest support of it, yet he well understood that he owed not his high position to any good-will or kindness, but to the mere necessities of the usurper.