Herakleia Pontika was founded by settlers from Megara around 560 BCE and named for a cave nearby where Herakles was reputed to have entered the underworld.
An interesting dynamic existed in the city when the Megaran settlers conquered the natives, but agreed to never sell them for slavery outside of the region. Therefore, two classes of people lived in the area.
From 365 to 353 BCE, the city was ruled by a cruel tyrant called Klearchos. After he was assassinated, his brother Satyros took over as regent for his two sons Timotheos and Dionysios. When Timotheos became king, he installed his brother as a co-regent. When Timotheos died in 337 BCE, Dionysios became sole ruler.
Dionysios played his sides very well in becoming friends with Alexander the Great’s sister, Kleopatra of Macedon, who dissuaded Alexander from overrunning Herakleia. After Alexander the Great’s death, Dionysios joined with Perdikkas’ enemies, which turned out to be the right side.
Dionysios then took to several alliances to secure his position. He married Amastris, a Persian noblewoman and sent forces to assist Antigonos. He also gave one of his daughters to Antigonos’ nephew, Ptolemy (not from the Lagid line).
After Dionysios died in 306 BCE, his wife Amastris took over. She followed her ex-husband’s model by marrying Lysimachos, and thus securing her position. It’s not sure how strong the marriage was, as she seems to have moved back to Herakleia to rule.
In 284 BCE, Amastris was drowned by her two sons from Dionysios. They wished to rule themselves, however it was short lived. Lysimachos arrived shortly after and had both executed. He then took control of Herakleia until his death in 281 BCE.
Herakleia then stayed independent for some time, even receiving some territory that had revolted back, courtesy of Nikomedes I of Bithynia. The city remained mostly independent until it was annexed by the Romans.
Approximate founding of Kallatis by settlers from Herakleia Pontika.
Herakleia Pontika founded by colonists from Megara and named after Herakles, who it was believed entered the underworld through a nearby cave.
Klearchos obtains a band of mercenaries and takes control of Herakleia Pontika.
Klearchos is murdered at Herakleia Pontika by Chion and Leon. His brother Satyros takes over.
Death of Timotheos of Herakleia Pontika. His brother Dionysios is now the sole ruler.
July
After the Battle of the Granicus, Dionysios of Herakleia Pontika increases his power and the size of his kingdom.
Antigonos Monophthalmos sails to and secures Cyprus. He is given aid by Dionysios of Herakleia Pontika. Antigonos thus marries his nephew Ptolemaios to Dionysios’ daughter.
Polyperchon issues a decree to restore democratic governments in all cities to reduce the allure of Kassander. Those exiled due to this may return, with the exception of Amphissa, Pharkadon, Herakleia Pontika, Trikka, and Megalopolis.
Lysimachos takes control of Herakleia Pontika and marries Amastris.
Demetrios Poliorketes blockades the Hellespont, forcing Pleistarchos to turn back. Pleistarchos’ ship is destroyed in a storm on the way to Herakleia and he survives by clinging to the wreckage.
Amastris travels to Sardis with Lysimachos, who turns his attention to Arsinoe II. Amastris returns to Herakleia Pontika.
Amastris is drowned by her two sons, Klearchos and Oxyathres. The two brothers take over Herakleia Pontika.
Lysimachos returns to Herakleia Pontika and is initially warm to Klearchos and Oxyathres, then kills them for drowning their mother and allows the city to return to democracy.
Arsinoe II begs Lysimachos to let her have Herakleia Pontika. He eventually relents, and she installs Herakleides of Kyme, who becomes tyrant.
March
When news of the death of Lysimachos reaches Herakleia Pontika, they seize the tyrant Herakleides, appoint Phokritos as governor, and make overtures to Seleukos.
July
Zipoetes, the first ruler in the Bithynian dynasty, lays waste to the territory around Herakleia Pontika.
April
Maximinus Daza takes Herakleia from Licinius after a short siege.