You are not the first to wonder why Pyrrhus gets so much high honors despite being, by all accounts, ultimately unsuccessful in the many wild and wonderful adventures that defined his life. I had a similar reaction when I heard that he ranked so highly on Hannibal's list of great commanders.

The story of Hannibal giving Pyrrhus such high praise comes from Plutarch and Appian, historians of the Roman imperial period who lived long after Pyrrhus. Both these writers have their own issues as sources that and I am oft-inclined to disbelieve some of the more fanciful anecdotes that are found in their work. Even so, both give us explanations as to why Pyrrhus gets such a good grade from Hannibal. Plutarch says that this admiration was based on the idea that Pyrrhus devoted himself to the study of tactics and military affairs, considering it his kingly duty to absorb himself in these matters and nothing else. Appian relates that Hannibal so respected Pyrrhus because of his sheer boldness, an important quality for a general. Apparently no two kings were more enterprising than Pyrrhus and Alexander in Hannibal's eyes.

Simply put, the high place Pyrrhus receives in the sources is owing to his unmatched dedication and capacity to be bold. Does he deserve this reputation? It depends on how you see his career. Whatever you think of him, you can't deny that he was determined. His family was turfed out of Epirus in 317 when he was only two. He returned to Epirus as King in 306 only to be overthrown again four years later. He got deeply involved in the wars of Alexander's successors, serving on the losing side at the decisive Battle of Ipsus in 301. He reclaimed Epirus in the early 290s and persevered until he became King of Macedon in 288 in a joint monarchy with a man named Lysimachus. However Lysimachus was cruel and ruthless and had forced Pyrrhus out of Macedon by 284. Undeterred, Pyrrhus got involved with the Romans, intervening on the side of Tarentum, an Italian Greek city state they were fighting. It was in this conflict, which raged on-and-off from 280-275, that the Pyrrhic victory at Asculum took place.

During his time on the western side of the Adriatic he also got involved in Sicily, the Greek inhabitants of which appealed to him to aid them in their ongoing trouble with Carthage. He acquiesced and, for a time ruled as King of Syracuse. He scored some impressive successes in Sicily but the cost of the war forced him to put heavy demands on the Sicilian Greeks. They resented this so he eventually left and returned to Italy where the Romans defeated him at Beneventum in 275.

He returned to Epirus and quickly managed to reclaim the throne of Macedon, then only tenuously held by a man named Gonatas. His final years were a hectic scramble as he moved from one war to another, going from his coup in Macedon to a nearly successful war against Sparta, and finally meeting his end against Gonatas at Argos in 272. Tradition maintains he was killed by a roof tile thrown by an old lady.

That's a very quick overview of Pyrrhus' life. I encourage you, and indeed anyone else who happens to read this, to learn more about him as he is a truly fascinating figure. In a sense, Plutarch and Appian are right. He was certainly dedicated to military affairs and his boldness is beyond question. Is that enough to put him second only to Alexander on Hannibal's all-time greats list? If nothing else, he was an influential figure whose name has been immortalized, although admittedly for less than enviable reasons. Whether that's worth a place in the top 3 generals of the ancient world is an open question. I hope what I have written can help in formulating an answer.