
Timoleon
07/11/22 • 45 min
Check out what I'm up to this summer and fall and see if you can learn some Greek and Latin with me.
Full Show Notes Available at https://plutarch.life/timoleon
Season 4 is brought to you by Hackett Publishing - Use the coupon code PLUTARCH for 20% off and free shipping at hackettpublishing.com
Important People
Timophanes - Timoleon’s brother and the first tyrant we meet in this story. His name, rather fittingly, means "seems honorable."
Dionysius II - The tyrant whom Dion overthrew, but did not execute. He returns to power after Dion’s death only to be replaced by Hicetas.
Hicetas - The tyrant who replaces Dionysius II, who had allied with the Carthaginians to gain power. Starting out allied with the Corinthians, he becomes Timoleon’s main enemy in the fight to free Syracuse.
Mago - Carthaginian general allied with Hicetas and leading a formidable navy. He’s the first Carthaginian general to “capture” Syracuse, though it’s Hicetas who hands the city over.
Plato - Though dead by the time Timoleon comes to power, he haunts this dialogue both in its analysis of tyranny and its understanding of justice.
Key Virtues and Vices
Justice (δίκη - dikē) - Plutarch argues (30.9) that Justice preserved Timoleon’s good fortune. With this in mind, it’s helpful to remember that Dion didn’t have the same good fortune, though he seems to have deserved it. Perhaps he stepped off the road of Justice and Plutarch allows us to decide where and when. Timoleon also puts justice and honor over convenience (5.1), his brother acts without justice (4.5) when he becomes tyrant, and Timoleon not only acts justly (5.1; 10.7; 29.6), but physically restores the courts of justice (22.3) to the democracy of Syracuse that before had to rely on the whims of the tyrant.
Gentleness (πραότης - praotēs) - Though not mentioned often, it's important for us to remember that this is a virtue listed explicitly in Aristotle's Ethics and one that Plutarch takes great interest in for his characters. Timoleon is introduced to us as gentle (3.4), but not with tyrants and base men. We're also told at the end that he dealt gently and justly with friends (37.5), but boldly and powerfully against barbarians (i.e. Carthaginians in this case). See Plutarch's "On the Moderation of Anger" or Aristotle's Ethics Book 4, Ch. 5 (1125b35) for a more thorough discussion of this virtue and its most obvious excess: anger.
Wisdom (φρονήσις - phronēsis) - Especially on the heels of Dion’s life, Timoleon just strikes us as lucky. Yet, Plutarch primes us in the preface (0.8) to read with an eye for his wise choices and not to judge every decision by its (usually positive) outcome. Plato's wisdom even helps men like Dionysius (15.4)
External Links
- Ambleside Online's Study Guide for Timoleon
- Herman Melville's Poem Timoleon, of which I read the eighth and final stanza in the podcast
- English Translation of Plutarch's Life of Timoleon
- Greek and English of Plutarch's Life of Timoleon (Perseus)
- Art of Manliness
Check out what I'm up to this summer and fall and see if you can learn some Greek and Latin with me.
Full Show Notes Available at https://plutarch.life/timoleon
Season 4 is brought to you by Hackett Publishing - Use the coupon code PLUTARCH for 20% off and free shipping at hackettpublishing.com
Important People
Timophanes - Timoleon’s brother and the first tyrant we meet in this story. His name, rather fittingly, means "seems honorable."
Dionysius II - The tyrant whom Dion overthrew, but did not execute. He returns to power after Dion’s death only to be replaced by Hicetas.
Hicetas - The tyrant who replaces Dionysius II, who had allied with the Carthaginians to gain power. Starting out allied with the Corinthians, he becomes Timoleon’s main enemy in the fight to free Syracuse.
Mago - Carthaginian general allied with Hicetas and leading a formidable navy. He’s the first Carthaginian general to “capture” Syracuse, though it’s Hicetas who hands the city over.
Plato - Though dead by the time Timoleon comes to power, he haunts this dialogue both in its analysis of tyranny and its understanding of justice.
Key Virtues and Vices
Justice (δίκη - dikē) - Plutarch argues (30.9) that Justice preserved Timoleon’s good fortune. With this in mind, it’s helpful to remember that Dion didn’t have the same good fortune, though he seems to have deserved it. Perhaps he stepped off the road of Justice and Plutarch allows us to decide where and when. Timoleon also puts justice and honor over convenience (5.1), his brother acts without justice (4.5) when he becomes tyrant, and Timoleon not only acts justly (5.1; 10.7; 29.6), but physically restores the courts of justice (22.3) to the democracy of Syracuse that before had to rely on the whims of the tyrant.
Gentleness (πραότης - praotēs) - Though not mentioned often, it's important for us to remember that this is a virtue listed explicitly in Aristotle's Ethics and one that Plutarch takes great interest in for his characters. Timoleon is introduced to us as gentle (3.4), but not with tyrants and base men. We're also told at the end that he dealt gently and justly with friends (37.5), but boldly and powerfully against barbarians (i.e. Carthaginians in this case). See Plutarch's "On the Moderation of Anger" or Aristotle's Ethics Book 4, Ch. 5 (1125b35) for a more thorough discussion of this virtue and its most obvious excess: anger.
Wisdom (φρονήσις - phronēsis) - Especially on the heels of Dion’s life, Timoleon just strikes us as lucky. Yet, Plutarch primes us in the preface (0.8) to read with an eye for his wise choices and not to judge every decision by its (usually positive) outcome. Plato's wisdom even helps men like Dionysius (15.4)
External Links
- Ambleside Online's Study Guide for Timoleon
- Herman Melville's Poem Timoleon, of which I read the eighth and final stanza in the podcast
- English Translation of Plutarch's Life of Timoleon
- Greek and English of Plutarch's Life of Timoleon (Perseus)
- Art of Manliness
Previous Episode

Dion
Check out what I'm up to this summer and fall and see if you can learn some Greek and Latin with me.
Full show notes available at https://plutarch.life/dion
Season 4 is brought to you by Hackett Publishing. Use coupon code PLUTARCH for 20% and free shipping in the US and Canada.
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 or nephew.
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...
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
- 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.
Next Episode

Alexander
Check out what I'm up to this summer and fall and see if you can learn some Greek and Latin with me.
Full Show Notes Available at https://plutarch.life/alexander
Season 4 is brought to you by Hackett Publishing - Use the coupon code PLUTARCH for 20% off and free shipping at hackettpublishing.com
Important People
-Bucephalus - Yes, a horse is an important character! Fiery, hard-working, and lasting till the edge of Alexander's empire, Bucephalus (ox-head) provides an analogue for us to see a fiery temperament tamed.
-Philip - Alexander’s ambitious father and the succesful military reformer who almost led an expedition against Persia himself. His untimely assassination makes that task fall to Alexander.
-Olympias - An ambitious and scheming mother, Olympias always pushes Alexander to do more and work harder. While at home, she frequently conflicts with Antipater, the regent Alexander left in charge of Macedonia in his decade-long absence.
-Darius III - The last Achaemenid emperor of Persia flees from Alexander twice but, overall, is treated well by his enemy. He didn’t choose his successor, but ultimatley respects the man who sits on the throne of Cyrus after his death.
-Poros - One of the last king-generals that Alexander defeats before turning around to head back home. Poros lives on the far side of the Indus River and earns Alexander’s respect in a hard-fought battle. Alexander keeps him in his current position and adds lands to his after defeating him.
-Aristotle - One of the greatest philosophers who ever lived worked as the personal tutor to Alexander the Great for at least two years. The two men continue to correspond later in life but some versions of the story have their relationship cool significantly after Alexander executes his grand-nephew, Callisthenes (cf. sections 53-55)
-Philotas - A contemporary of Alexander rising in the ranks under his father, Parmenio. Both experienced leaders who served under Philip and Alexander, Philotas’s pride finds him implicated in a conspiracy and Alexander kills him and his father.
-Clitus (Cleitus) - A member of Alexander’s companion cavalry who saves his life at The Battle of Granicus River. When he later tries to publicly correct Alexander for adopting too many Persian customs, the fight leads to his tragic death, which Alexander struggles to recover from.
-Callisthenes - Grand-nephew of Aristotle accompanying Alexander on the Persian Expedition. He acts as a proxy for Alexander's relationship with the ethical and political lessons Alexander had learned from Aristotle. When he dies (some reports say by Alexander's order, others do not), it seems Alexander lost his last link with his childhood education.
Important Places
-Thebes - Not just in Plutarch’s backyard, but the city punished for revolting after Philip’s death. It is burned to the ground and 30,000 of its inhabitant are sold into slavery. Plutarch thinks this must anger the god Dionysius, who was born close to Thebes.
-The Battle of Granicus River
-Battle of Issus
-The Siege of Tyre
-Alexandria
-The Battle of Gaugamela
-The Battle of Hydapses
Key Virtues and Vices
-Generosity
-Justice
-Friendship
-Ambition (φιλοτιμία)
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