Pyrrhus of Epirus in the context of "Megacles"

The Illyrian kingdom was an Illyrian political entity that existed on the western part of the Balkan Peninsula in ancient times. Regardless of the number of the alternately ruling dynasties, of their tribal affiliation, and of the actual extension of their kingdom, it represented an alliance of Illyrian tribes that united under the rulership of a single leader, expressly referred to as "King of the Illyrians" in ancient historical records (whether in Ancient Greek or in Latin). The monarchic superstructure of the Illyrian state coexisted with the Illyrian tribal communities and the republican system of the Illyrian koina.

The Enchele's polity was the earliest to emerge among Illyrians. The earliest known Illyrian king – Bardylis – emerged in southern Illyria around 400 BC, most likely centered in Dassaretis, a region along Lake Ohrid and east to the Prespa Lakes, located on the border between Macedon and Epirus. He aimed to make Illyria a regional power interfering with Macedon. He united many southern Illyrian tribes under his realm and defeated the Macedonians and Molossians several times, expanding his dominion over Upper Macedonia and Lynkestis and subjugating Macedon for several decades until he was decisively defeated by Philip II of Macedon. Before the Rise of Macedon Illyrians were the dominant power in the area. The kingdom of the Taulantii on the south-eastern coast of the Adriatic evidently reached its apex under Glaukias' rule and dominated southern Illyrian affairs in the late 4th century BC, exerting great influence on the Epirote state through the close ties with the Molossian king Pyrrhus.

In Greek mythology, Neoptolemus (/ˌniːəpˈtɒlɪməs/; Ancient Greek: Νεοπτόλεμος, romanized: Neoptólemos, lit. 'new warrior'), originally called Pyrrhus at birth (/ˈpɪrəs/; Πύρρος, Pýrrhos, 'red'), was the son of the mythical warrior Achilles and the princess Deidamia, and the brother of Oneiros. He became the progenitor of the ruling dynasty of the Molossians of ancient Epirus. In a reference to his pedigree, Neoptolemus was sometimes called Achillides (from his father Achilles' name) or, from his grandfather's or great-grandfather's names, Pelides or Aeacides. According to Plutarch, Neoptolemus was the ancestor of Pyrrhus of Epirus.

Epirus (/ɪˈpaɪrəs/; Epirote Greek: Ἄπειρος, Ápeiros; Attic Greek: Ἤπειρος, Ḗpeiros) was an ancient Greek kingdom, and later republic, located in the geographical region of Epirus, in parts of north-western Greece and southern Albania. Home to the ancient Epirotes, the state was bordered by the Aetolian League to the south, Ancient Thessaly and Ancient Macedonia to the east, and Illyrian tribes to the north. The Epirote king Pyrrhus is known to have made Epirus a powerful state in the wider Hellenistic world (during 297–272 BC) that was comparable to the likes of Macedon and Ancient Rome. Pyrrhus' armies also attempted an assault against the state of Ancient Rome during their unsuccessful campaign in what is now modern-day Italy.

The Roman expansion in Italy covers a series of conflicts in which Rome grew from being a small Italian city-state to be the ruler of the Italian region. Roman tradition attributes to the Roman kings the first war against the Sabines and the first conquests around the Alban Hills and down to the coast of Latium. The birth of the Roman Republic after the overthrow of the Etruscan monarch of Rome in 509 BC began a series of major wars between the Romans and the Etruscans. In 390 BC, Gauls from the north of Italy sacked Rome. In the second half of the 4th century BC Rome clashed repeatedly with the Samnites, a powerful tribal coalition of the Apennine region.

By the end of these wars, Rome had become the most powerful state in central Italy and began to expand to the north and to the south. The last threat to Roman hegemony came during the Pyrrhic War (280–275 BC) when Tarentum enlisted the aid of the Greek king Pyrrhus of Epirus to campaign in the North of Italy. Resistance in Etruria was finally crushed in 265–264 BC, the same year the First Punic War began and brought Roman forces outside of the peninsula for the first time. Starting from the First Punic War (264–241 BC) the territories subject to Roman rule also included Sicily (241 BC), Sardinia and Corsica (238 BC), islands transformed into provinces.

Epirus (/ɪˈpaɪrəs/) is a geographical and historical region in southeastern Europe, now shared between Greece and Albania. Classical Epirus roughly lay between the Pindus Mountains in the east and the Ionian Sea in the west, and between the Acroceraunian Mountains in the north and the Ambracian Gulf in the south. It is currently divided between the region of Epirus in northwestern Greece and the counties of Gjirokastër and Vlorë in southern Albania. The largest city and seat of the Greek administrative region of Epirus is Ioannina.

A rugged and mountainous region, in classical antiquity Epirus was the north-west area of ancient Greece. It was inhabited by the Greek tribes of the Chaonians, Molossians, and Thesprotians. It was home to the sanctuary of Dodona, the oldest oracle in ancient Greece, and the second most prestigious after Delphi. Unified into a single state in 370 BC by the Aeacidae dynasty, Epirus achieved fame during the reign of Pyrrhus of Epirus who fought the Roman Republic in a series of campaigns. Epirus subsequently became part of the Roman Republic along with the rest of Greece in 146 BC, which was followed by the Roman Empire and Eastern Roman Empire.

The history of Greek Sicily (Ancient Greek: Σικελία) began with the foundation of the first Greek colonies around the mid 8th century BC. The Greeks of Sicily were known as Siceliotes.

Over the following centuries many conflicts between the city-states occurred until around 276 BC Pyrrhus of Epirus managed to conquer the whole island except Carthaginian Lilybaeum. After the First Punic War in 241 BC the island was conquered by the Romans.

Agron (/ˈæɡrən, ˈæɡˌrɒn/; Ancient Greek: Ἄγρων) was an Illyrian king of the Ardiaean Kingdom in the 3rd century BC, ruling c. 250–231 BC. The son of Pleuratus II, Agron succeeded in reconquering southern Illyria, which had been under the control of Epirus since the time of Pyrrhus, and in extending Illyrian rule over many cities in the Adriatic region, including Corcyra, Epidamnos, and Pharos.

He is most famed for his decisive victory over the Aetolian League, a state in western Greece. Around 231 BC, Agron suddenly died after his triumph over the Aetolians. Pinnes, his son with his first wife Triteuta, officially succeeded his father as king in 231 BC, but the kingdom was ruled by Agron's second wife, Queen Teuta.

The Molossians (Greek: Μολοσσοί or Μολοττοί, romanized: Molossoi or Molottoi) were a group of ancient Greek tribes which inhabited the region of Epirus in classical antiquity. Together with the Chaonians and the Thesprotians, they formed the main tribal groupings of the northwestern Greek group. On their northern frontier, they neighbored the Chaonians and on their southern frontier neighbored the kingdom of the Thesprotians. They formed their own state around 370 BC and were part of the League of Epirus. The most famous Molossian ruler was Pyrrhus of Epirus, considered one of the greatest generals of antiquity. The Molossians sided with the Macedonians against Rome in the Third Macedonian War (171–168 BC) and were defeated. Following the war, the region witnessed devastation while a considerable number of Molossians and other Epirotes were enslaved and transported to the Roman Republic, in the Italian Peninsula.