Plutarch's Life of Dion - Podcast and Show Notes by Tom Cox

Important People

Dionysius I (the elder) – Tyrant of Syracuse taking power shortly after the Peloponnesian War and reigning until 367 BC. For some authors, he’s the textbook tyrant in the way he held on to power, the fear that prevented him from trusting almost anyone (except his nephew Dion), and his cruelty. Though Plutarch doesn’t mention it, this is the tyrant who shows up in stories like Damon and Pythias or The Sword of Damocles. Dionysius is called D-Prime in this podcast so that we don’t confused him with his son, D-II, or nephew, Dion.

Dionysius II (the younger) – Less accomplished and intelligent than his father, Dionysius does manage to rule Syracuse not once, but twice. We’ll see his comeback in Timoleon’s story but in this biography we’ll see him attempt to go from neglected son of a tyrant to philosopher-king. It doesn’t work out well. He’ll be called D-2 in the podcast to distinguish him from his father and uncle.

Dion – The main character of our tale and one of Plato’s best and brightest students. When he fails to convert either the elder or younger tyrant to philosophy, he finds himself exiled, stripped of most of his wealth, and finally discovers his wife has been ordered by the tyrant to marry another man. This means war and Dion takes it to Syracuse. Can he become the next philosopher-king? Will he instead train up a virtuous democracy to overthrow fifty years of tyranny? Tune in to find out!

Plato – Yep. Plato was a real person who had a real life outside of his dialogues (in which he never makes himself a character). You’ll want to check out Plato’s Seventh Letter for another perspective on the events in this Life. If you haven’t read this life, though, Plato’s Seventh Letter will be a great deal more obscure.

Philistus – An accomplished military mind banished by D-Prime but recalled by D-2, Philistus had taken up his pen in exile and written as a historian. As a political enemy and counterweight to Plato’s influence on D-2, Plutarch has a lot of reason to hate this man.

Heracleides – The perfidious but fun-loving rival as Dion tries to tame the tyrannical democracy. Heracleides would rather feed the beast and the tensions certainly mount as Dion fights not one tyrant, but two.

Callippus – This perfidious Athenian doesn’t seem important until the end… and then he’s fatally important.

Important Places

Corinth – Mother city (metropolis, μητρόπολις) of Syracuse and prosperous city on the Peloponnesus.

Syracuse – 5 major neighborhoods

Ortygia – The original island settled by the Corinthians who founded Syracuse. It still contained
Achradina – The heights of the mainland settlement overlooking the ocean and the Neapolis region, famous for the stone quarries in which the Athenians died during the Peloponnesian Wars and after which Dionysius would use for political prisoners.
Neapolis – the most recent addition to the city, North and West of Achradina and Ortygia, but enclosed by the fortifications D-Prime built
Tyche – district of Neapolis near the Northern gates of the city
Epipolae – high plateau in the Neapolis, included in the walls D-Prime built

Key Virtues + Vices

Courage (ἀνδρεία – manliness, courage) – Dionysius I and Plato have a fight about what virtue consists in. Plato concedes that andreia is important but then proves publicly that tyrants are the least manly men.

Aloofness – Dion struggles to win friends and influence people.

Outline of Plutarch’s Biography of Dion

C. 1 – A Corinthian? A Teacher’s Influence

Why Troy can’t be mad at Corinth (Corinth attacked and allied with Troy through different people: cf. Glaucus).
Dion and Brutus both students of Plato, one directly and Brutus nourished on his teachings.
Their lives prove that wisdom and justice united with power and good fortune make for a beautiful and marvelous life.
The principles of those who have received the same training flow into their lives, creating a parallel harmony visible even to outsiders.

C. 2 – Common Fortunes: Evil Spirits?

Their fortunes similar, and over this they had no control.
Both died young and unable to achieve what they had set out to do.
The gods warned both of their coming death.
Some might dismiss this warning, denying that any man in his right mind is ever visited by a specter.
But Dion and Brutus’s characters, trained in philosophy and hardened to the ascetic life, were still shaken enough by the dreams as to tell fiends. Thus, we may have to accept as fact that
Malignant spirits walk the earth attacking virtuous men so that they don’t attain a better end than the spirits themselves.
But enough of this, I’ll start with Dion.

C. 3 – A Tale of Two Tyrant Wives

Just before the end of the Peloponnesian War (405 BC), Dionysius the Elder marries Hermocrates (a general and leader of the Syracusans during the Sicilian expedition).
Whose life is made so difficult by the Syracusans that she kills herself.
Dionysius now marries two women: Doris of Locri and Aristomache (a native Syracusan).
He married both wives the same day, and he devoted himself equally to each one.
The Syracusans wished that the Syracusan wife were more favored, but Doris had a first-born son and thus made up for her foreign status.
Aristomache still barren until Doris’s mother comes under suspicion and is put to death for rendering Aristomache barren.

C. 4 – The Philosopher’s Pupil

Dion is Aristomache’s brother, first respected as a brother-in-law and then admired in his own right.
Dion even entrusted with the treasury (as long as the treasurers informed Dionysius the same day).
Dion had natural virtues enhanced by his meeting Plato around 388 BC
Divine guidance brought these two men together for laying the foundation of freedom in Syracuse.
Of all the companions of Plato, Dion sets himself apart as the quickest and most adept in virtue.
Plutarch accepts the seventh letter as genuine and in it sees that someone like Dion can be raised in a court of servitude which counts pleasure and luxury as the highest good.
but still be led to love philosophy. Dion’s soul quickly ignited with this love and in his youth he expected he could help the tyrant Dionysius I love the same things. So Dion introduces Plato to Dionysius I.

C. 5 – Dionysius I Rejects Philosophy

In their first meeting, they discuss human virtue, which centered on manliness. Plato asserted that tyrants were least manly and that the life of the just was the most blessed.
Dionysius annoyed at such speech, but even more annoyed to see people listening and being convinced.
Dionysius grows angry and asks why Plato has come.
Plato says he came to seek a virtuous man, and Dionysius tells him he hasn’t found one yet.
Dion sends Plato back, because he wanted to return to Athens.
D I tries to pay a Spartan on the same return voyage to kill Plato, if possible, and if not, to sell him into slavery. Dionysius thought that since he was a wise man, he’d be just as happy in slavery as in freedom.
The Spartan sells Plato on Aegina, and island at war with Athens at the time.
Dion still trusted by Dionysius in spite of his friendship with Plato, even using him as an ambassador to Carthage.
Dion spoke more freely than most courtiers around Dionysius. Dionysius makes a joke about an earlier tyrant, and Dion is the only one to correct him, pointing out how much better the former tyrant was than the current one.
Gelon ruled well as a tyrant; Dionysius not so much.

C. 6 – Tyrannical Succession

Dionysius had two daughters by Aristomache, named Prudence and Virtue. Prudence married Dionysius, making Dion now the uncle to the heir. Virtue married a brother of Dionysius, who died, and so Dion married his own niece… (Plutarch gives no comment on this arrangement)
When Dionysius was on his deathbed, Dion tries to negotiate for settlements for the children of Aristomache that will keep them safe in the coming succession.
The doctors don’t like anyone having close contact with Dionysius, so they shoo Dion away and give Dionysius a sleeping potion that finishes him off (according to Timaeus).
When Dionysius II (young Dionysius) calls together his friends, Dion gievs teh soundest and most mature advice.
Carthage is threatening again and Dion offers to take care of it. If young Dionysius wants peace, Dion will sail to Africa as envoy and negotiate it. If young Dionysius wants war, Dion will provide 50 ships for the war, maintaining them from his own money.

C. 7 – The Young Tyrant’s Court

Dionysius marveled at Dion’s magnanimity and zeal.
All the others surrounding the young tyrant immediately began to sow seeds of discontent about Dion: he must be trying to use his naval power to hand the tyranny on to Dionysius’s half-siblings, the children of his father’s other wife Aristomache, who were his nieces and nephews.
They really hate him because he lives differently than them and doesn’t mingle.
His other courtiers were always arranging pleasures and flatteries for the young tyrant… corrupting him further than his poort education already had.
The tyranny is softened like iron in the fire, not blunted by clemency but love of leisure.
Thus, everything Dionysius had built into the tyranny for fear and control gradually weakened the longer Dionyisus II ruled.
Once, supposedly, Dionysius partied for 90 days straight, rejecting any and all political business that came to his door.

C. 8 – Dion’s Judgment

Dion would not participate in these things, so the sycophants give vicious names to Dion’s vices.
They would not distinguish his advice from reproach and they saw his refusal to participate in debauchery as despising the men who participated.
Dion’s character had gravitas and aloofness that often seemed harsh or repellent to many. He was often criticzed for being more rude or harsh than necessary in his dealings with everyone.
Plutarch thinks the 4th letter is genuine, wherein Plato warns him that being strongly self-willed is a recipe for being alone.
Dion knew already that he was the first and most powerful in court because he was necessary for the running of Syracuse, not because anyone in the court liked him or respected him.

C. 9 – Dionysius I’s Legacy – Overprotective Parenting and Suspicious Tyranny

Thus, Dion wanted to see Dionysius II receive a liberal education (free way of spending time, or spending time for freedom), so that he would learn at first to fear virtue less and then even to delight in it.
D II mostly had been kept sheltered, so that his father could prevent him from being used as a political tool against him. So D II spent most of his childhood playing with miniatures (little wagons and lampstands).
D I so suspicious that the barber had to trim his hair with live coal rather than scissors.
Everyone who visited D I was given clothes they had to wear and thus the guards watched them remove all their other clothes, preventing anyone from sneaking into his presence armed.
Once, D I’s brother wanted to explain something, so he needed to draw a diagram on the ground. He took a spear from a nearby bodyguard and began drawing in the sand with it. D I ordered that bodyguard member to be put to death for handing off his spear.
He was especially suspicious of his friends who seemed to have a mind, since they would rather be tyrants themselves than serve one.
He slew another member of his bodyguard for admitting that he had a dream about killing the tyrant.
The man who grew angry with Plato for not publicly declaring him as the manliest of all men, was so besieged by his own fear and cowardice.

C. 10 – Dion’s pitch to D II

Dion encourages D II to study, and asks the best philosophers to come to the Syracusan court.
He should learn from the beautiful orderer of the universe, who brings things from chaos to order.
Thus he would also find happiness for himself and his people at the same time, replacing forced obedience with goodwill born of a just and moderate king rather than a tyrant.
D I had thought the unbreakable bonds of tyranny were fear, force, and a big navy. Dion argued that they were actually goodwill, ardor, and favor engendered by virtue and justice.
After all, how could Dionysius dress himself in the best clothes and not also want equal adornment and finery for his speech and his soul.

C. 11 – Plato v. Philistus

Dionysius seems passionate to learn from Plato, even wanting to befriend the man.
Dion asks directly and enlists the help of other philosophers in southern Italy to ask Plato to come (back) to Syracuse, to steady the youthful soul from being tossed about by his power.
Plato, mostly to prove that he wasn’t just a theoretician, and also because he knew what a great good it would do to heal the leader of so many people, came to Syracuse.
The other cronies of the court recall an educated man name Philistus from exile and hope that his influence can balance Plato’s.
Philistus had helped D I establish his tyranny and had been the captain of the citadel guard. He also may have been intimate with D I’s mother.
Philistus banished for not asking permission about whom to marry.
Philistus flees to Adria (MAP?) and there wrote histories, which do not survive but Plutarch had access to. He was recalled as a “staunch friend of the tyranny”

C. 12 – Dion’s “Plan”

Dion now implicated in a rumored plot to overthrow D II.
Dion really hoped, with Plato’s help, to make D II a fit ruler.
But, if D II refused, Dion was supposedly planning from the beginning to depose him and restore democracy, not because he loved it but because he saw no virtuous aristocracy to fall back on.

C. 13 – Plato Arrives

Sometimes after 368 BC, Plato arrives, greeted with great acclaim and honor.
A royal chariot escorted him from his ship and D II offered a thanksgiving sacrifice on his arrival as a gift for all of Syracuse.
D II began to show signs of modesty in banquets, actions of his court, and all dealings with the public so that people began to hope for permanent change.
The fad for philosophy becomes all the rage. The palace filled with the dust of all those doing their geometric proofs.
In response to a prayer that the tyranny might be unshaken for generations, D II once responded “Stop Cursing Us”
Philistus seemed to be losing ground to Plato’s influence.

C. 14 – Dion Exiled; Plato Isolated

The abuse of Dion becomes concerted and public, calling him a bewitcher of D II with Plato’s teachings, and the plot for Dion’s nephews to get the power is “revealed.”
Some seemed angry that the Athenians, who couldn’t take Syracuse with large land and sea forces (see Life of Nicias) should now
overthrow Syracuse by the means of one wise man, who persuaded D II to disband his bodyguard (10,000 strong), abandon 400 triremes, 10,000 cavalry and countless infantry in order to pursue Academic philosophy.
D II grows suspicious as these rumors swirl, and later turns openly hostile. Then a letter comes to D II where Dion insists the Carthaginian envoys include him in any discussions with D II, which looks like Dion is trying to run the city.
Dionysius consults with Philistus and pretends for a time to bring Dion closer to himself.
Then, when walking alone with him down the beach, he confronts him with the letter and accuses him on conspiring with the Carthaginians.
Dion tried to defend himself but D II doesn’t listen and places him on a ship right then and exiles him from Syracuse.

C. 15 – The Immediate Aftermath of Dion’s Exile

The women close to the tyrant mourn the loss of Dion. but the citizens of Syracuse seem hopeful of a change in government, thinking Dion would return to a take on the tyrant and his toadies?
Dionysius is afraid, so he claims only that he sent Dion on a journey so that D II’s anger didn’t make him do something worse.
He allows Dion’s friends to load up two ships with as many of his belongings as can fit and send them to the Peloponnesus where Dion will live in exile.
Dion had princely wealth, and his friends dispatch much of this wealth to him immediately.
With all this wealth among the mainland Greeks, he becomes a brilliant symbol of the power and wealth of the tyrant of Syracuse.

C. 16 – D II Jealous Love for Plato

Plato put under house arrest inside the acropolis, though under a pretense of hospitality.
D II grows jealous of Plato’s love for Dion and wants to be considered Plato’s best student, fawning over Plato in an attempt to win him over.
D II yo-yos back and forth between being desperately jealous of Plato and begging for forgiveness. He loved hearing the philosophical lectures, but also hated being corrected by his friends who loved only pleasure.
When war breaks out with Carthage(?), D II sends Plato away, promising to summon Dion back when peace was declared.
He doesn’t fulfill the promise, but at least continues sending Dion the revenues from his lands.
D II asks Plato to keep quiet and say no evil things about him among the Greeks.

C. 17 – Dion’s Reputation in Greece

Plato and Dion now working together in the Academy in Athens.
Dion lives with Callippus in the city, but buys a country estate that he later gives to Speussipus, his closest friend while at the Academy.
Plato trying to soften Dion’s cold aloofness by association with men or warmer and more charming presence.
Speusippus was just the ticket.
Plato chosen by lot to pay for a chorus of boys to sing in a Festival Dionysia, Dion covers all Plato’s expenses. Plato encourages this goodwill-gathering, hoping it will increase Dion’s prestige in Athens.
Dion visited other cities as well, showing off the fruits of philosophy to so many parts of Greece: moderation, virtue, manliness, and devotion to letters and philosophy.
Many cities vote him public decrees of honor.
The Spartans give him honorary Spartan citizenship, even though D II was the zealous ally of Thebes against Sparta at the time (date??).
When visiting a wealthy and influential Megaran,
he was forced to wait and rather than being annoyed as many of his friends were, he pointed out that they were often this busy when in Syracuse and made so many important people wait to speak to them.

C. 18 – D II’s Jealousy

D II grows jealous of Dion’s popularity among the Greeks and cuts off his revenues and confiscates his estates.
Dion also gets together another band of philosophers, to prove that he’s still pursuing philosophy.
He thus uses poorly the little he had learned from Plato and looks foolish.
Now, D II flip-flops and longs for Plato to return.
Like a tyrant, he was always “extravagant in his desires and headstrong in every undertaking,” he persuaded Archytas, a Pythagorean in southern Italy, to promise Plato’s perfect treatment.
D II sends a trireme and personal philosophical escort to pick up Plato.
D II also promises mercy to Dion if Plato comes, but nothing for Dion without Plato’s arrival.
Dion also receives letters from his family asking for Plato’s return.
Thus, Plato returns for a third time to Scylla and Charybdis (mythologically located in the straits between Sicily and Italy).

C. 19 – Third Time’s A Charm?

Both D II and all the citizens of Syracuse excited by Plato’s return, hoping philosophy would win over tyranny.
Women also earnest,
Plato was allowed to come into the presence of D II without being searched.
Plato brings up Dion shortly after arriving…
D II always finds excuses and coverup for not dealing with the Dion situation.
One of Plato’s close friends correctly predicts an eclipse and D II gives him a talent of silver.
Then another philosopher, as a joke, predicts that Plato and Dionysius will soon be enemies…
D II sells Dion’s estate and puts Plato in charge of the mercenaries, who have long hated him since they think Plato’s philosophy will convince D II to disband his bodyguard.

C. 20 – Plato’s Swift Dismissal

Archytas, the philosopher who had guaranteed Plato’s safety, now sends a trireme to pick up the philosopher in the awkward position in charge of the bodyguard.
D II dismisses him with farewell banquets and the thought that Plato will take D II’s bad reputation and noise it abroad.
Plato responded that he had much better things to discuss at the Academy than D II.
Plato’s own words (Epistle VII) do not entirely agree with the account Plutarch gives, and Plutarch knows it.

C. 21 – Dion’s Wife, the Last Straw

Dion grows angry, particularly about the forced remarriage of his wife.
Plato was asked on his first dismissal to see how Dion felt about his wife being remarried.
A rumor had spread that Dion and his wife did not get along (no one knew if it was true).
Plato responded in veiled (but obvious) enough terms that Dion would be angry if Dionysius should “carry out the business.”
When hope of reconciliation, recall, or return was in the air, Dion’s wife and son tolerated at court.
When Plato left Sicily the second time, then Dion handed Arete to Timocrates, against her will. In this, he did not even follow the reasonableness of his father.
Dionysius I had married his sister off to Polyxenus, who was ran away from Sicily when he became an enemy to the tyrant.
D I berated his sister for not telling him. The sister defended herself saying if she had known, she would’ve gone with him, because she’d prefer to be the wife of Polyxenus than the sister of D I.
Admired for her bold speech (παρρησιασμένης) and still honored after the tyranny broke up, with people willingly attending her funeral. “This is a digression παρέκβασιν, but not a useless one”

C. 22 – Dion Turns to War

While Dion turns to war, Plato backs away on account of guest-friendship with D II and his age (~65-70). Speusippus, Plato’s cousin, and many from the Academy do cooperate with Dion helping him to free Sicily.
Speusippus had gotten to know Syracuse when he was waiting for Plato to be released.
He earned the Syracusans’ trust and they now begged Dion, through Speusippus, to come himself as soon as possible, regardless of whether or not he returned in force.
Dion collected mercenaries secretly.
Other philosophers lent their aid.
Miltas, a seer and student of the Academy, joins in as well.
The tyrants had banished about 1000 men, only 25 of whom joined Dion in this quest. The rest were cowards ἀποδειλιάσαντες
800 men convene on the island of Zacynthus, having no match in experience, daring, or training.

C. 23 – The Army Gathers

The mercenaries to not react kindly to the news, which had before this been kept from them, that they’d be tasked with taking down Dionysius’s tyranny.
Dion and another eloquent Greek, Alcimenes, convince them of the soundness of the plan and call them all the leaders of the Syracusans, who are ready for revolt.
Midsummer, Etesian winds blowing full, and a full moon. Dion sacrifices to Apollo in a solemn procession with his soldiers, all fully armed.
At the stadium of Zacynthus, Dion hosts a feast. As they admired his wealth, they became even more convinced he would succeed for who in his right mind would risk this exorbitant wealth for an unsure enterprise?

C. 24 – Omens on Both Sides

Eclipse right as the sacrifice begins! Dion not phased.
Soldiers, greatly shaken, reassured by Miltas, the seer’s, interpretation: something currently great will be eclipsed!
So it is Dionysius’s tyranny which will be eclipsed.
Privately, he reports the omen of the bees swarming on the sterns of Dion’s boat as a promise of initial success but ultimate failure.
Dionysius also received omens at the time.
An eagle took a spear from one of his bodyguards and dropped it into the sea.
The water nearest the base of the acropolis (ocean water of the Mediterranean sea) tasted fresh and clean for an entire day.
An entire litter of pigs was born without ears.
The seers interpret the latter as the people no longer listening to Dionysius and the former as a change from bitter to sweet circumstances.
The eagle, as the servant of Zeus and the spear as the emblem of power meant that the highest god wanted to take the power of this tyranny.

C. 25 – Dion’s Journey

About 35 ships set sail for Syracuse, most of Dion’s soldiers in two merchant transport ships.
Dion brought arms for many more who would join them in Syracuse and enough provisions to allow them to cross the open sea, since they knew if they stayed close to the coast Dionysius (or Philistus) would see them coming.
Twelve days of sailing and on the thirteenth day they reach Pachynus (southernmost tip of Sicily, about 40 miles south of Syracuse).
The pilot urges them to disembark here so that they don’t have to pull back from this shore and wait several more days tossed at sea before a favorable wind allows them to land again.
Dion does not want to land so close to the enemy, so he keeps sailing along the coast.
A strong wind blows them away from shore and, at the rise of Arcturus, a menacing storm threatens.
The storm brings them close to being smashed against some sheer cliffs off the African coast (find Cercina on a map).
As the storm abates, they discover that they’re at the Heads of the Great Syrtis (bay of Libya, 500 miles away from Sicily.
But now the water and air were becalmed and they were closer to Africa than Sicily.
Little by little, the wind rises and comes from the right direction,
Bringing them to a part of Sicily that the Carthaginians control (Minoa).
Synalus, the Carthaginian commander, was a guest-friend of Dion’s, but before he realized these men were Dion’s, he was trying to prevent them from landing.
His soldiers landed roughly, but killed no one, because Dion had forbidden it and captured the city.
Once Dion and Synalus recognize each other, Dion returns the city to Synalus’s control.

C. 26 – Misfired Messages

The most encouraging news was that D II had recently sailed to Italy with 80 ships, thus leaving Syracuse empty of its tyrant.
Dion’s men demand that he lead them straight to Syracuse—no rest!
Dropping off his unnecessary baggage to follow him later, Dion marches straight for Syracuse.
Dion strengthened already on his way by allied troops: cavalry from Agrigento and infantry from Gela.
Timocrates, Dion’s wife’s second husband, hears of Dion’s approach and warns D II.
Everyone in the city excited, but keeping quiet because it still seems like a rumor (distrust and fear).
The fate of the messenger: first meets a friend who is just finishing a sacrifice to the gods and he takes from that friend a portion of meat and sticks it in his bag.
Then he lays down in the woods by the side of the road to sleep.
A wolf comes, attracted by the smell of meat, and grabs the meat and the message at the same time.
When the man awoke and couldn’t find the letter, he decides the best course of action would be to disappear.

C. 27 – Dion Bears Down on Syracuse

Dion pulls more support to himself as he marches: rural Syracusans and Camarinaean (MAP).
By threatening to attack other smaller cities first, Dion pulls off many of Timocrates’s allies, who rush home to defend their cities.
Dion continues the forced march even as he hears more good news and wakes his men at midnight to reach the river Anapus (10 furlongs from the city… where Nicias and his men finally surrendered?).
Here Dion sacrifices to the rising sun and, seeing Dion crowned with a wreath for sacrifice, everyone else crowns himself as if victor.
His ranks had grown from 800 to 5,000 men, their “enthusiasm making up for their lack of equipment…exhorting one another with joyful shouts to win their liberty.”

C. 28 – Dion Enters Syracuse

The best men of the city meet Dion at the gates while the rest of the citizen body takes care of those who had acted as informers and toadies to the tyrant.
Timocrates can’t make it into his fortified position on the acropolis, so he flees the city on horseback, full of fear.
Dion enters with Megacles, his brother, and the Athenian Callippus by his side.
The Syracusans welcom the incoming soldiers as if they’re part of a religious procession, restoring democracy after 48 years of absence.

C. 29 – Dion’s First Speech and Generalship

Dion officially announces the tyranny ended and the people’s freedom.
As he climbs to address the people from the Achradina, the people offer meat and flowers, prayers and vow as if he were a god.
Standing on top of a giant sundial that Dionysius had erected, Dion encourages the citizens to take hold of their liberty.
Dion and Megacles given generalship with absolute power (αὐτοκράτορας στρατήγους), and 20 colleagues serving with him, half of them returned exiles.
Seems like a good omen that he delivered the speech on a monument of D II’s, but then it also seems like a bad omen when he is made general in the same place, as if his power will change as quickly as the time does.
Dion captures the Epipolae and then walls off the acropolis for a siege.
Dionysius returns via his ships to the acropolis and Dion’s arms arrive from Eastern Sicily that had been carried overland by wagon.
Dion distributes these arms and runs out quickly, because all the citizens are eager to help and arms themselves however they can.

C. 30 – Negotiations…BATTLE!

Dionysius tries to deal privately with Dion, who insists that everything be public in speaking to a free people. D II suggests easier taxes and lighter military service.
The Syracusans laugh these offers down. Dion asks him to step down and so gain immunity from prosecution, considering they were/are related by marriage.
Both parties meet at the acropolis to finalize concessions on both sides.
It seemed, from the negotiations, that Dionysius would renounce his tyranny.
But D II was just pretending and, while negotiations are happening, sends out drunk mercenaries into the city.
All the Syracusans surprised and scared by the attack, but Dion’s mercenaries come to the rescue.
The Syracusans then just get in the way of Dion’s men cleaning the mess up quickly. Since no one could hear Dion’s orders, he led by example and charged directly toward the barbarians.
Everyone recognizes Dion and both friend and enemy close on him so that his person becomes the center of the fray.
Being on the older side, he barely handled this, was wounded in the hand and took several holes to his shield and breastplate.
Falling to the ground, Dion was pulled out of the fray and put Timonides in charge. Then, mounting a horse, Dion rides around the city calming the Syracusans and collecting his other mercenaries for a second attack on D II’s barbarians.
Since D II’s men has rather unexpectedly encountered resistance almost immediately, they fell back into the acropolis as this second attack falls upon them.
They are driven back into the citadel with great force, but Dion had lost 74 men and D II likely an equal number.

C. 31 – Letters from Dion’s Family

Syracusans reward Dion’s mercenaries with 100 minas, and they turn some of that into a gold crown for Dion himself.
Dionysius now sends letters from the women of Dion’s family (wife and mother), still in custody of Dionysius.
Disagreement about the name of Dion’s son (was is Hipparinus or Aretaeus), Plutarch sides with Timonides as a source because Timonides was a friend and fellow-soldier of Dion.
The people of Syracuse listen to all the letters, but give Dion the option to open the letter from his son privately. Dion opts for it to be read aloud.
It sounded like entreaty, but was written to turn the Syracusans to hatred against Dion.
It reminded them of all the work Dion had done on behalf of the tyranny; the threats hanging over his family members, and a request that he not abolish, but assume, the tyranny! His son reminds him that he should not give liberty to citizens who hate him and should instead look out for the safety of his family and his own power.

C. 32 – Dion’s Rival

No Syracusan seems to notice the temptations that Dion had already for so long been resisiting: acting for honor and justice over many strong claims of family and past service.
Instead, the letter sows suspicion and makes them look around for other leaders to balance Dion’s authority. Heracleides returns from exile at this ripe moment.
Heracleides had also served in a military role under the tyrant, but Plutarch tells us immediately that he is “irresolute, fickle, and unreliable, especially relating to power or glory”
He and Dion had had a falling out in the Peloponnesus and they had decided to attack Dionysius separately (H. has 10 ships: 7 war vessels (triremes) and 3 transport ships).
Heracleides courts the multitude and is a gifted speaker, particularly when compared to Dion’s cold aloofness. The demos now back in power seeks flattery from their leaders, not strategy.

C. 33 – Heracleides’s Resistance

Heracleides appointed admiral in an assembly the Syracusans call themselves (i.e. Dion didn’t call this one).
Dion complains that they had taken away something they’d already given him (i.e. total power) if someone else controlled the navy. Then the Syracusans reluctantly revoked their hasty decree.
Dion gently reproached Heracleides for not focusing on their common enemy and instead driving faction in the midst of a crisis. Then Dion calls a fresh assembly and appoints Heracleides admiral, even giving him a body-guard like his own (bad move!), which he had to convince the citizens to do.
Heracleides not simulates allegiance to Dion, but with the other hand also stimulates discontent and disturbances among the Syracusans, causing Dion much trouble.
Now Dion stuck between two difficult positions. If he arranges for Dionysius to leave the citadel, he’ll be thought too soft on the wicked tyrant, sparing him for familial feeling rather than doing what the democracy wants. If he prolongs the siege, they will complain he’s prolonging the war to stay in power and get them used to another tyrant.

C. 34 – Sosis’s Testimony

Sosis, a man base and bold, steps forward with an understanding of freedom of speech as bold license.
He says in the assembly that the Syracusans had blindly exchanged a drunk and stupid tyrant for a sober and watchful master.
He then left the assembly but was seen the next day bloody and naked, running through the streets as if he had just been beaten and was still pursued.
He comes into the assembly like this claiming that Dion’s mercenaries had treated him this way. Many start to grumble that these are the acts of a tyrant, punishing citizens for their free speech.
Dion calmly rises in the assembly and proves that Sosis had an inside man among the body-guards of Dionysius, who wanted the Syracusans to fight with one another making them easier to destroy.
Doctors look at Sosis’s wound and tell him that it had been done with a razor, not the pommel or blade of a sword or any blunt object.
Plutarch expands on how a sword wound would differ from a razor cut.
Some now come forward who said they’d met Sosis as he claimed he was “being pursued” and they ran to defend him.
All they could find further up the street was a bloody razor under a rock .

C. 35 – The End of Sosis and Philistus

Sosis’s own slaves then testify that he left his house early in the morning, before sunrise, carrying a razor. The people condemn him to death and apologize to Dion.
Yet everyone remained suspicious of his mercenaries, particularly because it seemed so much of the land battle was won and they fought now primarily on the see. Philistus had returned and swelled D II’s navy.
Shortly after, they defeat Philistus at sea and treat him savagely in defeat.
Ephorus reports that Philistus killed himself, but Timonides (again) reports in a letter to Speusippus that Philistus was taken alive.
They strip his corpse, decapitate him, and give his body to the young men of the city to drag around the Achradina until they throw it in the stone quarries.
Timaeus, another Syracusan source, says that they tied the rope to his leg and dragged him around because he had once given Dionysius the advice not to flee from his tyranny on a horse, but to wait until he was pulled off by the leg.
Philistus disagrees.

C. 36 – Plutarch’s Excursus on His Sources

Timaeus biassed against Philistus because he had so zealously supported tyranny. Plutarch goes lighter on those who desecrate the corpse if they had personally suffered under Philistus.
BUT those who write histories and were not harmed by him, but use his writings and then reproach him for calamities that may befall any of us… that’s not right (according to Plutarch).
Ephorus, too, heaps too many praises on Philistus. His skill as a historian seemed to be imaginative motives for base deeds and euphemistic alternatives for vices. Yet, Ephorus was himself a love of tyrants and an obvious admirer of luxury, power, wealth, and marriage alliances of tyrants.
(Plutarch’s Middle Way) – Don’t praise Philistus’s conduct and don’t gloat over his misfortunes.

C. 37 – D II Leaves; Heracleides Attacks Dion

With his best general, Philistus, dead D II offers to surrender the acropolis.
D II demands only that he be allowed to retreat to Italy and enjoy his revenues from a piece of land he owns near Syracuse.
Dion won’t negotiate without the people, and the people refuse even to hear the offer, driving away D II’s ambassadors.
D II hands the reins to Apollocrates, his oldest son, and sails away at the first opportunity. Heracleides doesn’t notice.
Heracleides doesn’t look very good to the people now, so he proposes, through an intermediary, the redistribution of the land to promote a real equality.
Then Heracleides publicly supports this measure and adds that they should stop paying Dion’s mercenaries and elect another general than Dion.
So, the people still weak from the sickness of tyranny, attempt to stand up against Dion, their doctor, who is trying to get them back to full strength.

C. 38 – Dion Replaced and Repulsed

Powerful thunderstorms for two weeks in midsummer prevent them from meeting to replace Dion.
Then, while the voting was about to begin, an ox broke away from its driver and ran for the theater.
It threw that section of the city into confusion , covering the same area that the enemy would later occupy themselves.
Ignoring these obvious omens, the Syracusans elect 25 generals, one of whom was Heracleides, then contact Dion’s mercenaries without his knowledge, asking them to leave his service and join them as citizens.
The mercenaries, fully armed, accompany Dion out of the city, doing no harm but hurling verbal abuse at those who treated Dion so ungratefully.
Then the citizen-mob set upon the mercenaries, thinking that because they were small in number, they could be easily overthrown now and never be a problem again.

C. 39 – Dion’s Choice

Dion now has to choose to fight his fellow citizens or defend the men he brought here.
Dion orders his men not to charge, but just to run forward, shout, and shake their weapons. Even this is enough to scatter the Syracusans who thought they would resist.
The Syracusans are so embarrassed by this, they arm and pursue Dion again.
They meet him at a river, but Dion isn’t as mild as he was in the city and sets his troops up in full battle array. They then flee more disgracefully than the first time.

C. 40 – Leontini v. Syracuse

Dion goes to Leontini where he is warmly received and his men are given citizenship. The Leontines send an embassy to Syracuse demanding justice for the mercenaries.
Syracusans denounce Dion via envoys, but Leontines, after discussion, still think Dion in the right.
Since the generals now listen to the people, and not the other way around, the Syracusans act pridefully and abide by their decision in repelling Dion.

C. 41 – Another Changing Tide

Dionysius II now sends aid via ship to those still holed up in the acropolis (including his son).
Then the Syracusans attack Nypsius (the newly-arrived naval commander sent by Dionysius) and win a battle in which they take four ships.
But then, they celebrate as if they already have the acropolis and Nypsius sees his opportunity.
Nypsius attacks their siege-works and releases some of his troops into the city.
The Syracusans are slow to oppose it as they pull themselves out of their cups.
So already the city was being sacked before even being conquered, and the Syracusan generals gave up.

C. 42 – Summon Dion!

No one wants to say Dion’s name aloud because they’re all ashamed of their “ingratitude and stupidity.”
Under necessity, some of the allies suggest that Dion be summoned from Leontini.
When the idea was first raised, many Syracusans shout and weep for joy, praying that he will just appear, making them more bold and fearless with his own boldness.
A delegation is dispatched to Dion asking for help.
At sunset, they arrive at Leontini.
They fall at Dion’s feet telling him everything.
Many bystanders hear the story as well, seeing the desperation in the manner of the envoys.
Dion assembles his men and lets the envoys tell their story.

C. 43 – Dion’s Decision

Profound silence follows the envoys’ plea. Then Dion rose but could not speak without weeping, but his men understood.
When he had recovered a little, he asked them to deliberate on the course of action.
For himself, as a Syracusan, he’d rather seek his grave among the blazing ruin of his native city than simply preserve his own life.
He calls on them, if they want to, to save the city their ancestors (Corinthians) had founded.
If you abstain, then know that you still have my thanks for your past bravery and zeal on our behalf. Remember that I, Dion, neither abandoned you when you were wronged, nor my fellow citizens when they were in distress.
His mercenaries cut him off with acclamations that they should hasten to Syracuse.
Dion orders his men to eat and pack, for they will close on Syracuse at night!

C. 44 – Syracuse Sacked; Mixed Messages

Meanwhile, D II’s soldiers had had Syracuse to themselves for a whole day, falling back to the acropolis at night with few losses.
Some citizens now thought their situation wasn’t dire enough to need Dion, really, and so they suggest that if he arrives with his mercenaries, he should be refused entrance.
Mixed messages are sent to Dion. Some asking him to come faster and other asking him to stop.
Thus, he sometimes marched slowly and at other times quickly, depending on the message he had most recently received.
The Syracusans who want to resist Dion take control of the gates, but the mercenaries sally forth from the acropolis AGAIN and tear down the entire siege works and begin sacking the city again.
Now not only men, but women and children are slaughtered and taken prisoner.
D II now just hated the citizens, and thus would Syracuse be a tomb if he couldn’t be tyrant.
Thus, all parts of the city now are lit on fire and looted.
Syracusans openly fleeing are caught, some are driven into their own homes which are then ignited, some building now falling into the streets as they burn.

C. 45 – Dion, finally, Arrives!

Now the gates opened unanimously to Dion, but he had stopped marching in haste since he had last hear that the enemy had returned to the acropolis.
Now as day broke, messages come to Dion that the city has been taken, and more messages asking him to hurry.
Finally messages from from Heracleides and Theodotus that no resistance remained and the city was being destroyed.
At this point, he and his troops break into a run while still more than 7 miles from Syracuse.
His troops burst through the gate into the Hecatompedon (field for hecatomb offerings = 100 cows offered at the same time).
Immediately he send his light-armed troops to charge the mercenaries and give the Syracusans heart. Then he divides his regular infantry into columns, giving leadership for attacking different parts of the city at once.

C. 46 – The Price of Victory

Having prepped and prayed, Dion was greeted by shouts of joy and called savior and god. His mercenaries are greeted as fellow citizens.
Dion led the charge through fire, blood, and dead bodies int he streets.
The enemy had grown savage, concentrating their forces on the now-demolished siege wall. The fire certainly slowed Dion’s progress through the city, often endangering the lives of his soldiers.
They ran through clouds of smoke, falling buildings, streets still on fire, trying not to break ranks.
The Syracusans encouraged them with shouts wherever they could and they pushed back Nypsius’s men.
No immediate victory celebration was possible for they had to put out the fire and spent most of the remaining night doing so.

C. 47 – Dion’s Virtue Toward Those Who Had Wronged Him

Most of the popular leaders exiled themselves by morning, but Heracleides and Theodotes asked Dion for forgiveness.
They admitted that Dion was better than they and could show greater mastery of his anger for their ingrattitude. In virtue, they admitted, they were certainly his inferior.
Dion’s friends recommended not to spare such base men, since those trying to please the mob were as dangerous, and as common, as tyranny.
Dion explained to his friends that he had not just trained for war, but at the Academy had trained how to conquer anger, envy, and all contention.
Being kind to friends proved no self-mastery, only to those who had wronged you.
He’d rather be superior to Heracleides in goodness and justice, not just power and wisdom.
Success in war had still to be shared with fortune
Envy had led H to act faithlessly, but vengeance, even if justified, would be motivated by the same weakness.
Dion is confident that even baseness can be conquered by frequent benefaction and converted to gratitude.

C. 48 – Heracleides’ Rises Again to Resetnment

Dion sets Heracleides and Theodotes free.
Asking the Syracusans only to bring wood, Dion puts his mercenaries to work re-building the siege wall, which they accomplish in a single night while all the Syracusans rest.
He buries the dead, ransoms the 2000 prisoners, and then calls an assembly.
H suggests they give Dion full powers by land and sea (again, and ironically what H had already weakened earlier).
The regular people annoyed that H would lose his position as admiral, since they considered him more a man of the people than Dion.
Dion gave in to them and restored H to his command at sea. When they once again asked for redistribution of the land, he resisted on this point and the regular citizens began to dislike him again.
H begins to sow seeds of discontent again with his sailors and soldiers and in secret communication with D II through a Spartan named Pharax.
As this suspicion grew, the difficulties in Syracuse increase.
Dion now at a loss, blamed by his friends for strengthening a man they had said should be put out of the way.

C. 49 – More Perfidy from Heracleides

Pharax, working with D II and camped near Agrigento, Dion doesn’t want to engage until he’s ready but H and his sailors tell Dion that he’s prolonging the war.
Dion attacks and loses, but tries a second time.
He then gets news that H is on his way back to Syracuse with the fleet, to get control of the city and shut Dion out.
He immediately sets out with his most reliable men and covers 88 miles, reaching the gate of the city by 9 a.m. the next day.
H arrived too late and thus had no plan, but he meets a Spartan (Gaesylus) who claims he had been sent to lead the Syracusans, as Gylippus was during the Syracusan expedition 75 years ago (Nicias 19).
H takes him into his company and secretly communicates with the Syracusans that they should accept their Spartan leader.
Dion responds that the Syracusans have enough commanders, and points out that he’s an honorary citizen of Sparta already, so he counts as a Spartan commander. The Spartan gives up and comes to broker the reconciliation between H and Dion, promising to avenge Dion is H does any more mischief.

C. 50 – Tyranny Departs (Tyrant’s Family Reunited)

The Syracusans break up their fleet and focused on their siege of the acropolis.
No one brings aid to the besieged and they ultimately give up and negotiate with Dion.
Handing over the citadel and the equipment, the rest of D II’s family sail away to join him.
Dion allows him to depart and all of Syracuse watches their freedom begin as his five ships fade into the distance.
Plutarch comments that they are rightfully proud since they, with so few resources, overthrew the greatest tyranny that ever was!

C. 51 – Dion’s Family Reunited

Dion’s mother and son come running out to greet him, but his wife follows shortly behind in tears, ashamed that she had lived as wife with another man.
His mother, Aristomache, leads him to his wife and reminds him in a speech how unhappy they were while he was exiled,
and removed all sorrow except the sorrow of this woman, forced to marry another man while her husband was still alive.
The choice is yours Dion, should she greet you as uncle or husband?
Dion, crying, embraced his wife and told both she and his son to return to his house, where he also lived as he put the Acropolis back in order.

C. 52 – An Academic in Syracuse

No Dion thanks his friends, allies, and mercenaries with fitting gifts.
While he himself lives in simplicity, which makes men wonder because not only Sicily and Carthage look at him, but all of Greece, regarded as he was the greatest of men alive.
But all the while his table, dress, and habits are as if he still lived at Plato’s Academy, rather than living like a soldier who feasted loudly as solace for their other dangers.
Plato wrote to him that the whole world was watching (4th Letter), but Dion kept his attention focused on the Academy and what he had learned there. It was their good opinion he cared about keeping.
His cold gravity remained, however, and set him at a distance from the people he was trying to rehabilitate for democracy.
He was not naturally gracious and also wanted to put a curb on Syracusans letting themselves go too much (into license and luxury).

C. 53 – Heracleidies (Finally) Killed

H returns to opposing Dion; when Dion invites him to attend a council meeting, he says that as a private citizen he belongs only in the Assembly.
Then he publicly denounces Dion for not demolishing the citadel of tyranny, and for stopping the citizens from exhuming D I, and for asking Corinth for advisors, not seeking any among the Syracusans.
Dion did do these things, even the latter, because he had a particular government he wanted to establish.
He wanted to curb pure democracy for he agreed with Plato that a pure democracy is not united (Republic Book VIII) but is many poleis vying for power against one another. Dion wanted a mixture of royal and democratic power, after the Cretan or Spartan model, where an aristocracy presides and administers most important affairs.
He now knows that H will never be anything other than fickle, turbulent, and seditious, so he allows those who want to kill him to do so.
Many Syracusans keenly resent his death, but Dion gave him a magnificent funeral, accompanied the body to burial, and spoke to the people they saw that it really was either Dion or Heracleides.

C. 54 – The Conspiracy of Callippus, Fellow Mystic

Callippus, an Athenian friend of Dion who had originally struck up his friendship when they were both initiated into the mystery-cult of Dionysius, was another right-hand man of Dion, entering with a special victory garland after winning distinction in battle.
Callippus sees an opportunity since he is favored by Dionysius’s men and the common people of Syracuse have no leader.
He bribes some of Dion’s mercenaries into killing him.
Since he would always report the soldier’s talk to Dion, Dion trusted him to meet secretly with whoever he wanted among the mercenaries and he used this as an opportunity to find the evil ones.
Dion was warned about the plot, but assumed Callippus was always following orders in talking secretly with the soldiers.

C. 55 – The Tragedy Begins

Dion warned by an apparition, when he was sitting alone, lost in thought.
He heard a noise at the far end of the colonnade in which he was sitting, and he saw a tall, imposing woman with the face and dress of a Fury on stage, sweeping the house with a broom.
He told his friends what he had seen and asked them to spend the night, but the portent did not return.
Tragically, a few days later, his son threw himself from the roof and died. No one is sure what caused the boys such pain or anger to provoke this.

C 56 – Conspiracy Completed

Dion stays out of the public eye as he grieves, but Callippus uses this opportunity to tell the people that Dion is now planning to invite Apollocrates, Dionysius’s son, to take over government in Syracuse again.
At this point, Dion, his wife, and his mother all are suspicious that something is happening.
Dion’s conscience now bothers him over Heracleides’s death and so he now declares himself ready to die many deaths if he had to live on guard of not only enemies but also friends.
As the women in Dion’s life investigate carefully, Callippus stays one step ahead of them by volunteering to come to them and denying any involvement. He promised to show fidelity in whatever way required.
They ask him to descend to a sanctuary of Demeter and Persephone where, after certain sacred rites were performed, he would don a purple robe of the goddess, hold a blazing torch, and recite the oath.
Yet, in spite of Callippus doing all this, his contempt for the gods is so intense that he waits for the same festival of Demeter and Persephone to commit his murder. This level of betrayal is more than just a friend killing a friend, it is a sacrilege of a mystagogue killing a mystic initiate.

C. 57 – Dion’s Death

Many conspirators involves. Some surround the house and some enter it while Dion is dining with friends.
The Zacynthians came in unarmed, planning originally to strangle Dion or bash his head in with a blunt object nearby.
This fails and they call their fellow conspirators who closed the doors for a sword. Not a single of Dion’s companions tries to help him, more worried about saving his own life.
A Syracusan hands in a short sword and they cut Dion’s throat as if he had been a victim for the altar (more religious imagery).
They cast his sister and his pregnant wife in prison, where she gives birth to a son. The son isn’t killed because Callippus has already fallen from power by the time the baby is born.

C. 58 – The End for Callippus but Not for Syracuse

Dion now has complete control in Syracuse and writes a letter to Athens, not bothered by the grave pollution he has brought upon himself.
So, Athens breeds good men of the highest excellence, but her bad men are of the worst baseness. The same soild produces honey and hemlock.
Cal did not remain long, as if the gods saw he needed a swift penalty.
He set out to take Catana, but in so doing lost Syracuse. (give more context: who took Syracuse from him? Why doesn’t Plutarch tell that story?) (cheese-grater joke)
He attacked Messana and in so doing lost most of his soldiers, among whom were Dion’s murderers. Then no other city in Sicily would receive him, so he crossed into Italy and took Rhegium.
He ran out of money to support his mercenaries who turn on him and execute him with the same short sword that was said to have killed Dion.
It was distinctive, and thus easy to identify as a Spartan blade, delicately and cunningly wrought.
Andromache and Arete (whose name means virtue) released from prison by Hicetas, a friend of Dion, thought to be faithful and honorable to them.
Afterwards, he arranged a ship for them to be taken to the Peloponnesus but he gave secret orders to the sailors to cut their throats and cast them into the sea. Some say, though, that they were thrown overboard alive.
Hicetas ultimately pays for his perfidy not only with his own death, but the death of his daughters, but that is Timoleon’s story and not Dion’s.