Settling in Athens, he lived a prosperous life until Dionysius II dispossessed him of his estates and income.
Recalled in 355 BC, he became master of the whole city but alienated the population with his imperious behaviour and financial demands.
Dion's attempts to liberate Sicily only brought the island political and social chaos which lasted for nearly 20 years.
[2] Dion joined Plato's philosophical school, where he excelled as a disciple,[1] and sought to inculcate Platonic maxims into the thoughts of Dionysius I.
He arranged a meeting between the philosopher and the despot, which ended in a quarrel after Plato spoke out against tyrannical leaders.
Plato escaped assassination by the agents of Dionysius I, but ended up being sold as an Athenian slave in Aegina.
On hearing of Dion's plans, Dionysius II then deliberately poisoned his father, who was unable to utter another word before passing away.
[1] He had, therefore, cloistered his son Dionysius II inside the Syracusan acropolis so, as he grew up, he lacked the knowledge, capabilities, political skills or personal strength expected of a future leader of men.
[1] Cornelius Nepos was of the view that Dionysius lacked his father’s strength of character and he paid too much attention to unscrupulous advisers who wished to discredit Dion.
[2] When he succeeded as tyrant of Syracuse, his entire court was composed of by licentious youngsters, who were completely disengaged from their political duties.
Dion offered either to travel to Carthage (to seek a diplomatic solution) or to furnish Syracuse with 50 new triremes with his own money to fight the Carthaginians.
[1][2] Facing increasing opposition to his plans, Dion began developing a plot, with generals Heracleides and Theodotes, to overthrow Dionysius.
Eventually Dion agreed with Heracleides to install a full democracy, by his wealthy patrician birth, he disliked this form of government.
[1] When Dionysius expressed the view that he no longer wished to rule as a tyrant, this alarmed Philistus and his supporters and they campaigned intensively against Dion.
In that letter, Dion recommended that the Carthaginians should consult him regarding a peace agreement, because he would provide all of Syracuse's demands to them.
Plato was confined inside the acropolis and received excellent treatment as an important guest, so he would not follow Dion.
[1] Thanks to these events, there was growing speculation in Syracuse that Aristomache, who was popular with her fellow citizens, would attempt to seize the power.
[1] Eventually, Dionysius decided to seize all of Dion's properties in Syracuse and stopped him receiving revenue from his estates.
However, despite his own helmsman's advice, Dion sailed further along the southern coast of Sicily where the fleet was hit by a storm and nearly smashed into pieces against the rocks near Cercina, in northern Africa.
As he was a personal friend of the governor Synalus of Heraclea Minoa, the Carthaginians offered lodging and plentiful supplies to Dion's expedition.
[1] Having learnt that Dionysius had sailed to Caulonia on the Italian peninsula with 80 ships, Dion's soldiers insisted on action.
Dion's foreign mercenaries had superior fighting skills and forced Dionysius' men to retreat back into the acropolis.
However, Dion undid this act on the grounds that his own consent was needed and then came forward himself to propose Heracleides for the role of admiral.
Heracleides then proposed to the popular assembly that: Dion opposed such plans but the Syracusans reacted decisively against what they saw as his oppressive government (which relied to a great extent on unpopular foreign mercenaries).
There, the Sicilian congress held a meeting, denouncing Syracuse, but the Syracusans responded that they preferred their actual liberties instead of a continuation of tyranny.
However, just as they were about to attack, reinforcements arrived led by a Campanian from Naples, Nypsius, who sailed his fleet into Syracuse's Great Harbour.
Instead he hoped to create a Platonic state and establish an aristocracy with some democratic limitations and with a king and a senate made up of aristocrats.
Heracleides refused joining the aristocratic senate even after an invitation of Dion and, again, the populist leader began conspiring.
Following the ceremony, Calippus broke his vow and planned to kill Dion on the day celebrating the goddess Persephone.
[1] Dion appears as a central character in Mary Renault's historical novel about classical Syracuse The Mask of Apollo (1966).