Pyrrhus Does Not Sail to Sicily

By all accounts, Phyrrus's choice to go to Sicily instead of Macedon and accept the throne was a strategic blunder for him. While capturing the island from both Carthage and Rome would have been good in the end he could not achieve it.

At first hailed as a liberator he did well until failing to take Carthage's main stronghold on the island, he failed to take it by siege so he opted to invade Carthage directly which did not turn out so well. The Greeks who had invited him did not want to man his ships as oarsmen and so when Pyrrhus tried to force them to they turned on him and force him to flee the island. By going to the island he also wasted time and allowed the Romans to reorganize themselves following his 'Pyhrric' victory.

If he had decided that going to Sicily would be a blunder and had instead marched east to take the Macedonian crown offered to him how would things have played out?
 
That was what I was thinking. He pretty much planned to cut the head off of Carthage by actually invading the city when he got no where with it during his Sicilian campaign but, none of the Greek settlers wanted to be conscripted into his fleet as oarsmen.

Well, taking the throne of Macedonia he would be quickly occupied by the Gauls and Antigonus II in Greece. I think he is more then capable of defeating both. Once that is done it depends on his temperament and the state of his Kingdom. It will be exhausted by the Gaul Invasion and the Antigonus campaign so he will have to sit and regain his forces. He possible could not wait and push his kingdom to the limits thus inciting revolt against him or he could distract himself (probably aiding the Ptolemies considering he was very close to Ptolemy) and wait and watch for when the Carthaginian and Roman alliance fails for the ATL Punic War and then attack Rome once more.
 
He'd better make sure that either Antigonus II is dead, or that EVERYONE accepts him as King in Macedonia and its Greek possessions (the first one's the better choice), before he runs back off to Sicily. He's inviting disaster if he just runs off to Sicily with whatever men he can find there as soon as he becomes King; someone's taking his crown away from him. It's the Macedonian way.

See, I think Sicily was actually the right choice for him. It's a lot safer a conquest for HIM, assuming he could get it down. The problem is that he didn't have a fleet after his first one was either defeated by Carthage or sunk in a storm (both equally as likely I'd say), which made his Siege of Lilybaeum much more difficult (as Carthage could reinforce and resupply the city at will) and would have enabled him to invade Carthage - keep that fleet afloat, and I think Pyrrhus wins in Sicily. Now, his successors would certainly have a difficult time keeping all of Sicily united, but the (Greek) island had shown it would unite under a capable strongman like Pyrrus, as Dionysus and Agathocles did before him.
 
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I am rather skeptical of his choice to adventure Westward. Even if he conquers Carthage he has a reinvigorated Roman army breathing down his neck as he over extends himself in North African campaigns. If he can consolidate a good portion of the Balkans he can tango with the Romans again.
 
I am rather skeptical of his choice to adventure Westward. Even if he conquers Carthage he has a reinvigorated Roman army breathing down his neck as he over extends himself in North African campaigns. If he can consolidate a good portion of the Balkans he can tango with the Romans again.

Rome would need a fleet that can challenge his first. And the will to chase him outside of the Italian peninsula.

The problem with Pyrrhus consolidating his rule in Macedonia, and making sure the Galatians were finished off, is that he's Pyrrhus - he would've wanted to march off on the next great campaign as soon as he's been made King and feels somewhat secure in that, which in Macedonia (especially at this time) is ill-advised for him having any chance at keeping that throne. He wasn't like Antigonus, who was willing to consolidate his rule over running off on campaigns outside of Greece - that's a large part of the reason why he won in the end. Militarily, he could easily retake the throne from Antigonus, and is likely to defeat the Galatians, but if he leaves immediately after succeeding at those two tasks to fight Rome again or go to Sicily (as is likely knowing him), there's a good chance that Antigonus takes the throne from him - even if Antigonus is dead, it wouldn't be crazy if another face pops up to take the crown from him, if he allows the opportunity (like he probably would).

He doesn't necessarily have to attack Carthage itself once he takes Lilybaeum - he could return to Italy to resume the war with Rome. However, a Carthaginian campaign is probably more likely, as fighting Carthage was his "project" at the time, and is probably the easier campaign. Agathocles had recently shown the promise of a campaign in Africa that Pyrrhus would have known all about, and, since he controls all of Sicily, and has control of the seas through his fleet surviving and Carthage's not (going with that as the PoD for my scenario), Pyrrhus' campaign is more likely to be successful than Agathocles' was. (I'm not saying that a Carthaginian campaign would be destined for success, or that even if it is successful, that it would be a long-term conquest for him and his successors, but he does definitely have a good shot at conquering it, or at least a better one than Agathocles had.) And it's probably the better choice than heading back off to Rome immediately after conquering Lilybaeum - while he would have a stronger base in Italy, in the Italian Greek cities, than he does in Africa... having full control over Sicily doesn't change his position enough to make me think it'd be too different from OTL's Beneventum campaign. While he might win victories on the battlefield over them, they'd probably be more "Pyrrhic" victories, and he still doesn't have the manpower base to compete with Rome. Rome's just too stubborn for his capabilities.
 
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