The Third Democracy

Greek Theater of Syracuse, 3 January 2006, detail from a photo by Michele Ponzio (fotovideomike) under CC BY-SA 2.0, via Wikimedia Commons

The “Third Democracy” is a classification used for the coins of Syracuse. This is specifically applied to coinage struck under Timoleon (ca. 344-317 BC). Coins from this era are routinely labeled “Timoleon and the Third Democracy” in auction catalogs. It is probably worth noting that “Third Democracy” is a modern analytical label, not an ancient one. The term applied to this coin from Syracuse prompted today's exploration of the tyrants and democracies of Syracuse.

The Coin: Sicily, Syracuse, Timoleon and the Third Democracy. first series 344-339/8 BC. Æ Hemidrachm (16.89g) Timoleontic Symmachy coinage (Greek συμμαχία, symmachía and alliance - literally “fighting together”). 1st series, circa 344-339/8 BC. Obv: Zeus Eleutherios

Rev: Thunderbolt; Eagle standing.

Note: Although not widely cited, this "short haired zeus" may be better attributed Dion 357-354 BCE. For the argument for that see (Giacomo Manganaro 1999). Reasoning: This type was imitated by many other cities (Leontini, Agyrion, Alaisa). Manganaro argues this widespread imitation makes sense only during the chaotic period of Dion (when Carthage was passive), not under Timoleon, who actually dissolved the political identity of some of these cities.

This coin shows Zeus Eleutherios (Zeus “of Freedom”), a type widely associated with democratic poleis and anti-tyrannical ideology. Read alongside the literary tradition that Timoleon dismantled tyrannical power and restored civic government, the choice of Zeus could invoke an anti-tyrant message. Zeus on civic bronze could be broadly protective/panhellenic, not necessarily narrowly constitutional.

Rizzo in 1939 identifies the profile not as a style of Timoleon's time, but as a copy of the 5th-century colossal statue commissioned after the fall of the Deinomenids. This would also effectively links the coin to the city's original victory over tyranny (whether initially issued by Dion or Timoleon).

"after deliberating on forming a democracy of their own they all voted unanimously to make a colossal statue of Zeus the Liberator and each year to celebrate with sacrifices the Festival of Liberation and hold games of distinction on the day on which they had overthrown the tyrant and liberated their native city"
-Ddiodorus Siculus, The Histories, XI.72.2

Early Syracuse (8th - early 5th century BCE) was an oligarchy governed by a narrow Corinthian-descended elite, the Gamoroí (“"landholders"). Political power rested with aristocratic families and citizenship and land ownership were tightly controlled. The broader population had little political agency.

Civic breakdown and internal conflict internal conflict led to the expulsion of the Gamoroí. Gelon seized power (485 BCE), ruling Syracuse as tyrant. He was succeeded by Hieron I and then Thrasybulus, whose expulsion in 466/465 BCE ended the Deinomenid dynasty.

The so-called "Second Democracy" (466/465–405 BCE) was in fact the first stable democratic constitution at Syracuse, established after the expulsion of the Deinomenid tyrants.

Sicily, Syracuse, Second Democracy, 466–405 BC, AR Tetradrachm (17.09g) circa 450–440 BC, Obv: Charioteer driving quadriga right, Nike flying above Rev: Head of Arethusa right, surrounded by dolphins, , Boehringer 566 (V285/R385), HGC 2, 1311

Sicily. Syracuse. "Second Democracy" following the expulsion of Thrasybulus (466/465 BCE). 461-60 BC. Obol AR 8mm., 0.6g. Diademed head of Arethusa right / Four spoke wheel. SNG ANS 116, Series XIIa-d (Boehringer 362-370).

Tyrant

The Greek word tyrannos (τύραννος) is thought to have been borrowed from the Lydian language (western Anatolia). It first appears in the seventh century BCE in the poetry of Archilochus, used to describe Gyges of Lydia.

At its origin, the term was not a moral judgment. It was a technical description of accession: a man who seized power outside the established hereditary framework.

• Basileus: a king who inherited authority according to custom and law.

• Tyrannos: a ruler who acquired power through force, deception, or popular acclaim rather than succession.

In the archaic period (seventh to sixth centuries BCE), tyranny was not inherently pejorative. Some tyrants - most famously Peisistratus at Athens - acted as populists who broke aristocratic monopolies, redistributed land, sponsored public works, and stabilized civic conflict.

In this early phase, tyrants could plausibly present themselves as champions of the people.

Sicily & Syracuse

It was Sicily that decisively transformed the meaning of the word. By the fourth century BCE, philosophers such as Plato and Aristotle repeatedly pointed to Sicilian examples when defining tyranny as the corrupt form of monarchy: rule by one man for his private advantage rather than the common good (Politics 1279b–1280a). In Roman political thought, tyrannus would further evolve to mean the seizure of the res publica - the people’s collective affairs - for personal ends.

Dionysius of Syracuse is the best remembered of these Sicilian tyrants, but he was not unique. The fourth century BCE saw the island dominated by military strongmen whose power rested on mercenaries rather than citizens. Hiketas of Leontini, Hippo of Messana, Mamercus of Catane, and Dionysius I and II of Syracuse were contemporaries in a landscape of endemic warlordism. This condition did not end until the intervention of Timoleon of Corinth.

Sicily, Akragas Æ Hexas. Circa 425-406 BC. Eagle, with head lowered, standing right on fish; [AKPA] across fields / Crab, two fish below; two pellets on either side of crab. HGC 2, 148.

The Archetype of Tyranny (Dionysius I)

Dionysius I (“the Elder”  405-367 BCE) first emerged as a demagogue during Syracuse’s crisis with Carthage. He accused the city’s generals and magistrates of incompetence and treason after the failure to defend Akragas, framing the traditional elite as enemies of the people (Diodorus Siculus 13.91–96). Akragas was attacked by Carthage in the Spring of 406 BC. The siege lasted approximately eight months, ending with the city's abandonment and sack in December 406 BCE.

When fined for violating civic decorum through inflammatory speech, his penalties were paid by the wealthy historian Philistus - allowing Dionysius to cultivate the persona of a persecuted reformer silenced by a corrupt system.

The decisive moment came with a manufactured security crisis. Claiming that aristocratic enemies sought his life, Dionysius persuaded the assembly to grant him a personal bodyguard of 600 men. This force, later expanded to 1,000 mercenaries, answered not to the city but to Dionysius alone. With it, he seized the citadel of Ortygia, physically separating executive power from the civic body and rendering popular institutions subordinate to armed force.

Once entrenched, Dionysius dismantled the old political order by reconstructing the citizen body itself. He confiscated aristocratic property, emancipated slaves, and extended citizenship to mercenaries and non-Greeks. A new electorate and army emerged whose wealth, status, and survival depended entirely on the tyrant. Loyalty was enforced structurally, not ideologically.

Sicily, Syracuse. Time of Dionysius I (405-367 BC). AE drachm or dilitron (31.83g). Fine, bankers mark. ΣYPA, head of Athena left, wearing wreathed Corinthian helmet pushed back on head, aegis on shoulder / Sea-star between two dolphins. HGC 2, 1436.

Later writers preserved illustrative anecdotes that, while stylized, convey contemporary understandings of tyranny:

• Poetic Justice (Diodorus Siculus, The Histories 15.6):When the poet Philoxenus criticized Dionysius’ verse, he was sent to the stone quarries. Asked for his opinion of a later poem, he replied only, “Take me back to the quarries.”

• The Sword of Damocles (Cicero, Tusculan Disputations 5.61): Dionysius demonstrated the insecurity of absolute power by seating a flatterer beneath a sword suspended by a single hair. (Cicero doesn't specific which Diocysius, but his description matches the elder: "Dionysius exercised his tyranny over the Syracusans thirty-eight years, being but twenty-five years old when he seized on the government.")

• Surveillance and Fear: (Aristotle, Politics 1313b or Book V, Chapter 11) describes the use of informants and provocateurs at Syracuse - attributed to earlier tyrants such as Hieron I but generalized as a device of tyranny - to fragment social trust and suppress dissent.

“to try not to be uninformed about any chance utterances or actions of any of the subjects, but to have spies like the women called 'provocatrices' at Syracuse and the 'sharp-ears' that used to be sent out by Hiero wherever there was any gathering or conference (for when men are afraid of spies of this sort they keep a check on their tongues, and if they do speak freely are less likely not to be found out)”
-Aristotle, Politics 1313b or Book V, Chapter 11

These stories are not evidence of personality quirks; they illustrate mechanisms of control: fear, dependency, surveillance, and isolation.

The Insecure Heir (Dionysius II)

When Dionysius I died, power passed to his son, Dionysius II ("the Younger"). He inherited absolute authority without the political skill that had created it. Suspicious of rivals and incapable of commanding loyalty, he soon banished his uncle and senior advisor Dion, accusing him of collusion with Carthage (Plutarch, Dion 6–7).

The problem was structural: a system designed to concentrate power in one man offered no mechanism for competent succession.

The Failed Liberation (Dion’s Coup)

From exile in Athens, Dion assembled a small mercenary force and, in 357 BCE, landed at Heraclea Minoa while Dionysius II was absent in Italy. The coup succeeded tactically. The tyrant fled. But the apparatus of tyranny remained intact.

Dion refused to dismantle the citadel of Ortygia or fully restore democratic institutions. Instead, he ruled as strategos autokrator, a position that replicated tyrannical authority under a different name. Without consensus, legitimacy, or institutional reconstruction, the coalition that had removed Dionysius fractured. Dion was assassinated by his own officers.

The tyrant had been removed; tyranny had not.

The Institutional Vacuum

The failure of the political class to provide order caused the citizenry to withdraw from public life, leaving the state vulnerable to opportunistic mercenaries. With the central executive dismantled, the city devolved into a cycle of "exchanging one tyrant for another".

• Dion (357–354 BC): Plutarch views Dion not as a failed usurper, but as a "physician" who attempted to impose a "strict and temperate regimen" on a society that was too sick with tyranny to accept the cure. He argues that while Dion possessed the "wisdom and justice" of a true Platonist, his haughtiness and severity made him irksome to the masses, preventing him from winning the affection necessary to rule effectively. His death was ordered by his former friend Callippus & fellow student of Plato. He was strangled and then had his throat cut.

• Callippus (354–352 BC): An Athenian intellectual and mystic who had marched with Dion. After orchestrating Dion’s murder, he seized power, claiming to be a "tyrant-slayer" but immediately established a tyranny of his own. He ruled for only thirteen months before being challenged by the son of Dionysius the Elder. He was defeated in battle and later murdered by his own mercenaries in Rhegium (supposedly with the same sword used to kill Dion).

• Hipparinus (352–351 BC): A son of Dionysius I (and half-brother to the exiled Dionysius II). He saw the chaos caused by Callippus as an opportunity to restore the family business. He attacked Syracuse with a mercenary force and seized control. His rule was brief and dissolute. Plutarch and Theopompus describe him as a drunkard who governed negligently. He was assassinated after reigning for just two years.

• Nisaeus (350–346 BC): Syracuse were so hollowed out by this continuous factional warfare that the city was "almost abandoned".

This was not chaos but predictable recurrence. The destruction of institutions without their replacement produced a vacuum filled repeatedly by men with armed followings.

An Improbable Return

This "institutional vacuum" paved the way for the unthinkable. Ten years after his expulsion, Dionysius II - now hardened and vengeful - collected a new force of mercenaries. He returned to Syracuse, ousted his half-brother Nisaeus, and reclaimed power, completing the cycle from despot to exile and back to master.

Restoring Democracy (Timoleon of Corinth)

Sicily, Syracuse. Timoleon and the Third Democracy (344-317 BC). AR 2 Litrae (Dilitron), 15mm, 1.5g, 12h

Obv: Female Janiform head; to the right, a dolphin.

Rev: Horse prancing left; star above.

Ref: SNG Copenhagen 718. SNG ANS 516.

The cycle was broken by Timoleon of Corinth in 344 BCE. Unlike previous “liberators”, Timoleon was not a displaced insider or aspiring autocrat. He was sent by Corinth at the request of Syracusan exiles and he arrived with limited forces and no claim to rule (Plutarch, Timoleon 2–5). [Note: this is perhaps a generous, even mythical view of Timoleon - Finley describes a less heroic Timoleon who certainly knew used the tools of a warlord tyrant: emergency command backed by brutal force.] Timoleon is also Corinth’s instrument for reasserting influence and creating a friendly order in a strategically critical region.

Timoleon defeated Dionysius II, who surrendered Ortygia without resistance, and he defeated the Carthaginians at the Crimissus River. Yet his significance lies not in military success, but in what followed.

Timoleon systematically dismantled the machinery of tyranny:

• He demolished the citadel of Ortygia, eliminating the physical separation between ruler and citizens.

• He disbanded mercenary forces and resettled Syracuse with new citizens from Greece, restoring a civic army.

• He reestablished democratic institutions and law courts, refusing permanent command.

Crucially, Timoleon declined power. After completing his reforms, he lived as a private citizen, appearing in public assemblies only when asked for advice. Plutarch emphasizes that he resisted honors that would have recreated personal authority (Timoleon 31–35).

This refusal was not moral heroism; it was institutional intelligence. By refusing to become indispensable, Timoleon forestalled the conditions that had sustained tyranny for a century - at least, until his death. The moment he died (c. 337 BCE), the unity he forged disintegrated. Syracuse drifted back toward oligarchy, with power coagulating in a narrow circle remembered as “The Six Hundred,” a wealthy clique that managed to dominate the polis through social influence rather than written law.

References

• Manganaro, G. (1999). Zeus Eleutherios – Zeus Kronos: Himera – Therma nel IV sec. a.C. Jahrbuch für Numismatik und Geldgeschichte, 48-49, 71–99.

• Rizzo, G. E. (1939). Intermezzo: Nuovi studi archeologici su le monete greche di Sicilia. Roma: Società “Magna Grecia”

• Rizzo, G. E. (1946). Monete greche della Sicilia. Roma: Libreria dello Stato.

• Finley, M. I. (1979). Ancient Sicily. Rowman and Littlefield.

• Diodorus Siculus. Library of History, Volume VI: Books 14–15.19. Oldfather CH, trans. Cambridge, MA: Harvard University Press; 1954:15.6.

• The Sword of Damocles (Cicero) Cicero. Tusculan Disputations. King JE, trans. Cambridge, MA: Harvard University Press; 1927:5.61.

• Surveillance and Fear (Aristotle) Aristotle. Politics. Rackham H, trans. Cambridge, MA: Harvard University Press; 1932:5.11 (1313b).

• Plutarch. (1918). The parallel lives: Dion (Vol. VI). (B. Perrin, Trans.). LacusCurtius.

• Plato. (2023). Plato’s letters: The political challenges of the philosophic life (A. Helfer, Trans.). Cornell University Press.

• Manganaro, Giacomo (1984). Dai mikrà kermata di argento al chalkokratos kassiteros in Sicilia nel V sec. a.C, in: Jahrbuch für Numismatik und Geldgeschichte. Spink. Manganaro identified a revealing piece of evidence: a Syracusan obol (of type 288 ff. or 365 ff., Boehringer) weighing 0.58 g (Pl. 2, 1) overstruck upon an obol of the Aitnaioi of the 'prawn' type which must have been modeled on the Series XIIe from Syracuse.

  

  Since Aitna only existed under that name between 475/4 and 461 BC (after Hieron I founded it and before the population was expelled). He lowers the date of the 'Demareteion' Series XIIe to 463 B.C., the 'prawn' obol of the Aitnaioi can be ascribed to Aitna-Inessa and dated around 461 B.C. The overstriking of this coin (the current wheel coin) in the Syracusan mint is well explained in the years around 461/0 B.C.; the Deinomenids having collapsed, the money of the Aitnaioi - enemies of the Syracusans - could be refused and overstruck in Syracuse.

• Lelouch, "The Obols of Syracuse", August 23, 2025