Originally Posted by
Satapatiš
Excuse me, but all your examples ended well for Pyrrhus except for Beneventum where he probably had to oppose two consular armies at the same time. This year saw two thriumphs for Roman consuls, presumably for the same engagement with Pyrrhus. And that battle wasn't possible for him to win, besides by then he was on his way out of Italy and only checking if he can't get the last chance of maybe winning a decisive battle against Rome. He didn't, but at the same time Romans failed at ending his threat... The entire resistance against the Republic only ended after the news of his death reached Italy.
There's a lot of effort on the Roman side to somehow soften the blow of writing about their inability to get rid of a one general from a Balkan backwater.
Pyrrhus situation wasn't the same as other Hellenic monarchs, mostly because Epirus barely counted as a kingdom. Compared to Macedon with tradition of being an actual kingdom, Epirus had kings in the same capacity as, for an example, Sparta. It's good to not look at Epirus as anything similar to their neighbours. Pyrrhus is sort of an exception coming from a Doric tribal federation where locals were used to having Aiakidai kings as hereditary generals and heads of the federation, but not to obeying them too hard. The position of kings there was so weak, the entire league could be existing even without them. The tribal assembly in Dodona was perfectly capable of acting without any royal family.
But in the game Epirus is more stable than Macedon (!).
On top of this... Pyrrhus wasn't even very popular in Italy. Italian Greeks had a very ambivalent stance towards him, his ambition of forging a hegemony there was fairly obvious. Samnites stuck with him to the end, but Samnites were always willing to stick with anyone giving them a shot at defeating Rome.
Good general, perhaps the best in his generation. But even the Ancients rated him high mostly as a general, not necessarily as a politician.
Probably he shouldn't be going to Italy in the first place, instead focusing on securing himself in Epirus...
...but we don't even know everything behind his decision of going to Italy and Epirus had interests across the sea even before his reign.