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King of Hellenistic Epirus whose costly military successes against Macedonia and Rome gave rise to the phrase “Pyrrhic victory.” His Memoirs and books on the art of war were quoted and praised by many ancient authors, including Cicero. He was the nephew and successor of Alexander 'the Molossian' and had also married a daughter of Agathocles of Syracuse, and seems to have regarded himself as a predestined successor to both.

Upon becoming ruler at the age of 12, Pyrrhus allied himself with Demetrius, son of Antigonus I Monophthalmus of Macedonia. Dethroned by an uprising in 302, Pyrrhus fought beside Demetrius in Asia and was sent to Alexandria as a hostage under the treaty between Ptolemy I Soter and Demetrius. Ptolemy befriended Pyrrhus and in 297 restored him to his kingdom.

At first Pyrrhus reigned with a kinsman, Neoptolemus, but soon he had his colleague assassinated. In 294 he exploited a dynastic quarrel in Macedonia to obtain the frontier areas of Parauaea and Tymphaea, along with Acarnania, Ampholochia, and Ambracia. Corcyra and Leucas were given to him in a marriage dowry. Next, he went to war against his former ally, now Demetrius I Poliorcetes of Macedonia. Pyrrhus took Thessaly and the western half of Macedonia and relieved Athens from Demetrius' siege, but was driven back into Epirus by Lysimachus (who had supplanted Demetrius) in 284.

Polybius on the Phalanx (book XVIII):

"In the case of the Romans also each soldier with his arms occupies a space of three feet in breadth (...) The consequence will be that one Roman must stand opposite two men in the first rank of the phalanx, so that he has to face and encounter ten pikes, and it is both impossible for a single man to cut through them all in time once they are at close quarters (...) So it is easy to see that, as I said at the beginning, nothing can withstand the charge of the phalanx as long as it preserves its characteristic formation and force.

What then is the reason of the Roman success, and was is it that defeats the purpose of those who use the phalanx? (...) It is acknowledged that the phalanx requires level and clear ground with no obstacles (...)

The Romans do not make their line equal in force to the enemy and expose all the legions to a frontal attack by the phalanx, but part of their forces remain in reserve and the rest engaged the enemy. Afterwards (the phalanx) leave behind the other parts of their own army, upon which the enemy's reserve have room enough in the space formerly held by the phalanx to attack no longer in front but appearing by a lateral movement on the flank and rear of the phalanx. (...)

The phalanx soldier can be of service neither in detachments nor singly, while the Roman formation is efficient. For every Roman soldier, once he is armed and sets about his business, can adapt himself equally well to every place and time and can meet attack from every quarter. He is likewise equally prepared and equally in condition whether he has to fight together with the whole army or with a part of it or in maniples or singly. "

In 281 Tarentum (in southern Italy) asked for Pyrrhus' assistance against Rome. He crossed to Italy with about 25,000 men, and in 280 won a complete, if costly, victory over a Roman army at Heraclea. In 279 Pyrrhus, again suffering heavy casualties, defeated the Romans at Ausculum (Ascoli Satriano) in Apulia.

He then crossed to Sicily (278) and, as “king of Sicily,” conquered most of the Punic province except Lilybaeum (Marsala). However, his despotic methods provoked a revolt of the Greek Sicilians, and in 276 (or early 275) he returned to Italy. In 275 he suffered heavy losses in a battle against Rome at Beneventum (Benevento).

The next year he invaded Macedonia, drove out Antigonus II Gonatas to Thessalonica, and took over the defecting Macedonian army. Suddenly abandoning Macedonia, however, he launched an unsuccessful attack on Sparta to restore Cleonymus (272). Violations of royal tombs by a garrison of Gauls at Aegae offended people, and Pyrrhus went south to invade the Peloponnese, leaving his son Ptolemy in charge. Antigonus Gonatas regained control of Macedonia and conveyed an army by sea to Corinth against Pyrrhus, whose son Ptolemy was killed in an ambush by the forces of King Areus of Sparta. At Argos Pyrrhus was trapped between the armies of the Macedonians and the Spartans and killed by a tile thrown from a rooftop in 272 BC, supposedly by an old woman seeing him fighting her son sword to sword in the street below. Other sources read that he was assassinated by a servant.