Dion (; ; 408–354 BC), tyrant of Syracuse in Magna Graecia, was the son of Hipparinus, and brother-in-law of Dionysius I of Syracuse. A disciple of Plato, he became Dionysius I's most trusted minister and adviser. However, his great wealth, his belief in Platonism and his ambition aroused the suspicions of Dionysius I's son and successor, Dionysius II. An indiscreet letter from Dion to the Carthaginians led to his banishment. Settling in Athens, he lived a prosperous life until Dionysius II dispossessed him of his estates and income. Landing in Sicily in 357 BC, he was successful in conquering Syracuse (other than the citadel). However, Dion soon quarrelled with the radical leader Heraclides and was forced into exile. Recalled in 355 BC, he became master of the whole city but alienated the population with his imperious behaviour and financial demands. His supporters abandoned him, and he was assassinated. Dion's attempts to liberate Sicily only brought the island political and social chaos which lasted for nearly 20 years.

Family Dion was the son of the Syracusan statesman Hipparinus, who had served with Dionysius I in the Syracusan army. Hipparinus' other children were Megacles and Aristomache. Aristomache married Dionysius I, who also married Doris of Locris at the same time. Although Dion's sister was popular with her fellow Syracusans, it was Doris who gave birth to Dionysius I's heir Dionysius II.

Aristomache had four children. Of these children, Sophrosyne married Dionysius II and Arete married Dion (with their son being called Hipparinus).

Advisor to Dionysius I As a trusted advisor to Dionysius I, Dion was given the most important diplomatic assignments. Dion excelled in managing the embassies that dealt with Carthage. Dionysius I was so satisfied with Dion's role as advisor that eventually Dion was authorized to withdraw money from the Syracusan treasury. The tyrant demanded, however, to be informed daily when he did so. Despite this requirement, Dion became extremely rich and his residence was magnificently furnished. Nonetheless, Dion occasionally criticized Dionysius I.

Since his youth, Dion had excelled in intellectual activities, particularly philosophy. In 387 BC he induced Dionysius I to invite Plato to Syracuse. Dion joined Plato's philosophical school, where he excelled as a disciple, 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. Despite this disagreement over Plato, Dion and Dionysius I's close relationship continued as before.

Dionysius I was on his deathbed when Dion attempted to discuss the succession with him. Dion hoped that Dionysius I would hand over the rule of Syracuse to him or to his family. However, his attempt to influence Dionysius I was stopped by Dionysius I's doctors who supported the younger Dionysius II. On hearing of Dion's plans, Dionysius II then deliberately poisoned his father, who was unable to utter another word before dying.

Dion and Dionysius II Dionysius I had dreaded that anyone might depose him treacherously. 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. When Dionysius I died in 367 BC, he was succeeded by Dionysius II. (References to Dionysius in this article hereafter refer to Dionysius II unless otherwise specified.) As an adult Dionysius was given to libertine practices. 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.

When he succeeded as tyrant of Syracuse, his entire court was composed of by licentious youngsters, who were completely disengaged from their political duties. The Syracusan institutions thus began to collapse. With his extensive political experience, Dion effectively ruled the city state. Soon, the people of Syracuse formed the view that Dion was the only one who might save the city.

In Dionysius' court, Dion proposed a response to the continuing Carthaginian threat. 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. Although Dionysius was delighted by these suggestions, his courtiers resented Dion's interventions. They suggested to Dionysus that Dion was trying to oust him in favour of the line of his sister Aristomache.

Dion concluded that educating Dionysius would be the key to resolving Syracuse's problems. With his philosophical training, Dion began teaching him about philosophical principles and the importance of good governance with the aim of making him a philosopher king. Such lessons sparked Dionysius' interest, so Plato was invited again to Syracuse. The experiment, in spite of a promising beginning, failed, with Dion's opponents gaining influence over Dionysius, leading to the philosopher Philistus being recalled (after he had been banished by the elder Dionysius) and then leading the opposition to Dion.

Facing increasing opposition to his plans, Dion began developing a plot, with generals Heracleides and Theodotes, to overthrow Dionysius. They agreed that they would wait in the hope of political reform, although they would oust Dionysius if this did not happen. Eventually Dion agreed with Heracleides to install a full democracy, by his wealthy patrician birth, he disliked this form of government.

Nonetheless, Plato arrived and was welcomed with much enthusiasm. Plato's conversations with Dionysius were said to have led to significant changes in Dionysius' views and behaviour, who, became sober and attentive, whereas his court continued its libertine practices. Then, during a traditional sacrifice, Dionysius openly stated that he did not wish to be a tyrant any longer.

Banishment 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. They insisted to Dionysius that Dion was the greatest of deceivers, who was intending to seize the realm for his own nephews. Dionysius believed their arguments so he adopted a hostile attitude towards Dion.

The situation reached a crisis point when Dionysius and Philistus intercepted a letter which had been sent by Dion to the Carthaginians. 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. Fearing a plot between Carthage and Dion and his supporters, Dionysius feigned a renewed friendship with Dion. They walked to the seashore where the despot showed the incriminating letter to Dion and, without giving Dion the opportunity to defend himself, immediately forced Dion into exile. Dion eventually made his way to Athens.

Plato was confined inside the acropolis and received excellent treatment as an important guest, so he would not follow Dion. Later, when war with Carthage restarted, Dionysius allowed the philosopher to depart Syracuse, promising Plato that he would allow Dion to return to Syracuse during the next summer.

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. Dionysius became aware of these sentiments and he attempted to address the situation. Publicly, he explained that Dion was temporarily in Athens so that he wouldn't provoke some violent backlash against Dionysius. Dion was allowed to hold onto his Syracusan estate so he was still receiving his usual revenues. Furthermore, Dionysius handed two ships to Dion's relatives so they could send his possessions after him to Athens.

Thus, Dion lived amongst the Athenian high society, dwelling with the patrician Athenian Calippus of Syracuse with whom he had become acquainted during the celebrations of the Eleusinian Mysteries. Additionally, Dion purchased a rural residence for his leisure. His closest friend was Speusippus.

Dionysius delayed Dion's return until the end of the war with Carthage. Dionysius recommended to Plato that Dion should not publicly criticise the Syracusan regime. Dion obeyed, staying within the Athenian Academy and studying philosophy.

Later Dion did begin travelling throughout Greece meeting many local statesmen. Dion was regarded as a celebrity and many Greek cities welcomed him. For instance, the Spartans endowed him with citizenship, although the city state was at war with Thebes and was allied with Dionysius.

Rebellion Eventually, Dionysius decided to seize all of Dion's properties in Syracuse and stopped him receiving revenue from his estates. Dionysius tried to mend his image by forcing Plato to visit him in Syracuse through public threats against Dion. The celebrated philosopher returned to Syracuse, but soon he and Dionysius began arguing bitterly about Dion's fate. The philosopher was jailed until an Athenian embassy arranged for his release. In his anger, Dionysus sold Dion's estate (keeping the proceeds) and compelled Dion's wife (and niece) Arete to marry the tyrant's close adviser, Timocrates.

In response, Dion sought to start a revolt in Syracuse against Dionysius and his supporters. Dion's closest friends advised him that in Syracuse, the population could be expected to enthusiastically join Dion's revolt, if only he could get to the city. They told him that Dion did not need to bring either weapons or soldiers.

Nevertheless, Dion managed to gather from his Greek supporters 800 soldiers who gathered on the Greek island of Zacynthus. Dion assured the leaders of the mercenaries that they would be made commanders once they defeated Dionysius.

In 357 BC, Dion's fleet sailed for Sicily. As his coming was expected, the Admiral Philistus had a fleet in Italian coastal waters ready to waylay him. So Dion sailed straight across the open sea. After 13 days, Dion's fleet reached Sicily at Pachynus. 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. The fleet had to wait for five days until a favourable southerly wind brought it back to Sicily. Dion was then able to land in Carthaginian territory. As he was a personal friend of the governor Synalus of Heraclea Minoa, the Carthaginians offered lodging and plentiful supplies to Dion's expedition.

Having learnt that Dionysius had sailed to Caulonia on the Italian peninsula with 80 ships, Dion's soldiers insisted on action. So Dion led his troops towards Syracuse. On the road through Agrigento, Gela, Camarina and the region surrounding Syracuse, they were joined by 5,000 Sicilians who wished to join the revolt. Near Akrai, Dion spread rumours that he would be attacking both Lentini and Campania. Dionysius' soldiers from these areas deserted Timocrates' forces to defend their respective towns. Then, during the night, Dion ordered the expedition to advance, and at daybreak, Dion launched his attack.

With the news of the arrival of Dion, the people of Syracuse slew the tyrant's supporters and Timocrates had to flee. Dion led his army into Syracuse. He wore brilliant armour and a garland crowned his head. Dion was accompanied by Megacles and Callipus. The local community leaders greeted them. Dion proclaimed that Dionysius was now deposed.