DBWI: Alexander goes for Persia?

I know, I know, it's a topic that comes up again and again. But I was reading up on Alexander lately, and found a poignant quote, where Alexander lamented that he never fought a foe that was his equal, and Persia was the obvious one. There are, of course, rumors that he was planning on invading in his twilight years, unafraid by that point of the Oracle's prophecy that he would never return to Macedon if he invaded Persia, but he died before he could truly set out. So, what would our world have been like if Alexander had went east? Would he have had a chance in his younger years, or would he have failed? And what of Karchidona and the Tyrrhenoi, had they not fallen to Alexander?
 
It's not surprising that this is a popular subject, given Ptolemy's famous scenario in his History of Alexander, where he contemplates Alexander going east, and concludes that Alexander would likely have conquered the whole Empire. I know a lot of determinists brush this scenario off as unrealistic at best and laughably ASB at worst, but a deeper look makes such a view less clear. Ptolemy's scenario really doesn't help, because it is riddled with historical inaccuracies and anti-Persian bias, but we shouldn't risk swinging to the other extreme and automatically and unilaterally dismiss such a scenario as ASB. Assuming Alexander decides to invade the Persian Empire, he actually has quite a few factors on his side. First are his own advantages: he has a highly trained and organized army that is definitely superior to the Achaemenid forces, he himself (assuming he and his generals are as good as OTL's) proved themselves to be great tacticians (most of the time), and he proved to be personally lucky in battle and willing to risk his life to lead charges. Even greater were the advantages of timing: his ascension to the throne coincided with dynastic turmoil within the Persian Empire, with the poisoning of two Emperors by Bagoas before Darius III forced Bagoas to take his own medicine (read: poison), and the fact that many Satraps and notables in the Empire were quite discontented with Persian rule. Another longer-term factor was that the Persian treasury was draining silver from the provinces that would never again be circulated throughout the Empire. This lead to troubles even for Satraps and landlords who could not come up with the hard currency to pay loans or debts, which only furthered discontent with Persian rule. A final factor that cannot be ignored was the Empire's increasing inability to hold down the western portion of its Empire. Egypt, for example, remained independent for a surprisingly long time, only subdued shortly before Alexander ascended to the throne. Asia Minor was effectively a demilitarized zone between Athens and Persia. I don't think a lot of people recognized how precarious the situation in the Persian Empire was at the time, or how well Darius III did even to keep his throne and Empire relatively intact. I would conclude from these factors that a lot actually depends on the nature of Alexander himself, and how lucky he gets. If Alexander retains an energetic "conquer the world" attitude as he had in his early years IOTL, he might've gone for the whole cake. If he had tired of conquest part of the way through, he might've been content in carving the western part of the Empire out for himself, leaving the East to its own devices. But from the Empire, he would inherit a slew of his own administrative and cultural problems that would hamper him and his successors. If even the conquest of Karchidona, Megas Hellas, and the Tyrrhenoi caused internal frictions and rebellions, then I can only imagine the cultural disruption that the entry of Hellenistic culture into the East would have.
As for Karchidona and the Tyrrhenoi, they could go in many different directions. I'd say that they'd likely remain regional powers, but anything is possible.
Anyways, this scenario's probably pretty unlikely. It would be so easy for Alexander to lose a battle, or die, or burn out, etc. I'm just saying that Ptolemy's scenario isn't totally ASB, it just needs some reworking to become plausible, even if unlikely.
 
It only made sense for Alexander to go west. He perfected his tactics against other Greek states, as well as against the Illyrian and Thracian tribes. Based on this experience and specialization of his army, it was far more practical to unite the Greeks and other similar peoples such as the Carthaginians before going on to take on the Persian Empire. Alexander did actually go on a brief scouting mission into Ionia, for which he founded the fort Alexandropolis (later called Alexandria) on what was previously Byzantion. However the Ionians failed to revolt as planned and Alexander cancelled the invasion.
 
But it did prove to be a jumping off point for Alexander II, who did conquer Persia. I know some speculate that it was unlikely that succession would have been so stable, knowing contemporary Macedonian dynastic politics, but because Alexander set up court in Macedon instead of Greece or Carthage makes it IMHO unlikely a general far away seizes power. It would be unlikely there would still be Greek speaking minorities as far as Afghanistan and Morocco today if a dynastic struggle ensued.
 
It did always seem strange for Alexander to mock Phillip as "The Man Who Would Lead You Into Persia" shortly before his death, but not pick up the mantle himself. It certainly seems that it was inevitable at the time.

Evidently the rise of Alexander to the throne changed that, especially with the rebellion of Epirus against his relatives. The initial reconquest may have changed his opinion.

I personally wondered if Alexander could have left the Western Campaigns to other commanders, they certainly were able to levy local manpower in conquered regions easily enough, and I think that would balance out with mutual campaigns. If Alexander took his best forces to Persia, but sent some Generals known more for their loyalty than their brilliance westward, he could likely conquer Anatolia and Italy at the same time, which would already be an impressive Empire compared to his father.

Interestingly would be some of the parallels. The Macedonian Fleet was required to defeat Carthage, and likely would be needed to defeat the Phoenician city states like Tyre, so that might well cause a problem - but once one falls the other would likely be inevitable because of the additional naval strength gained. I'd go so far that taking Tyre first would enable the Carthaginian War to be changed to a drawn out economic war whilst Alexander campaigns in Persia, and his Western Generals take Iberia, all while trapping Carthage to Africa so that it can't afford the armies it needs to defend itself.
 
It did always seem strange for Alexander to mock Phillip as "The Man Who Would Lead You Into Persia" shortly before his death, but not pick up the mantle himself.
Artaxerxes III absolutely spanked the Macedonians at Perinthus. Phillip's eastern ambitions were pretty laughable in light of that. Even when the ever bumbling Darius III was on the throne Alexander mostly played nice, even sending his son to Darius' court as a hostage.

But it did prove to be a jumping off point for Alexander II, who did conquer Persia. I know some speculate that it was unlikely that succession would have been so stable, knowing contemporary Macedonian dynastic politics, but because Alexander set up court in Macedon instead of Greece or Carthage makes it IMHO unlikely a general far away seizes power. It would be unlikely there would still be Greek speaking minorities as far as Afghanistan and Morocco today if a dynastic struggle ensued.
I'm not sure I'd call Alexander IV's* palace coup against the usurper Bessus a conquest (his campaigns against the Eastern Satraps are another story). Also, I think Alexander IV imposing Persian succession laws on the Macedonian throne was a bigger factor in the stability of the empire than the exact location of the capital, given that his son moved the capital to Alexandria on the Bosphorus without significant issue.

*OOC: Alexander the Great was already Alexander III
 
Artaxerxes III absolutely spanked the Macedonians at Perinthus. Phillip's eastern ambitions were pretty laughable in light of that. Even when the ever bumbling Darius III was on the throne Alexander mostly played nice, even sending his son to Darius' court as a hostage.

I'm not sure I'd call Alexander IV's* palace coup against the usurper Bessus a conquest (his campaigns against the Eastern Satraps are another story). Also, I think Alexander IV imposing Persian succession laws on the Macedonian throne was a bigger factor in the stability of the empire than the exact location of the capital, given that his son moved the capital to Alexandria on the Bosphorus without significant issue.

*OOC: Alexander the Great was already Alexander III

I think Perinthus is a distraction, more of a footnote to the Macedonian Reformation, Conquest and Inheritance Wars that Alexander III and Alexander IV fought (OOC : Pattersons Alexander II) Further "Alexandria on the Bosphorus" may have been its name for a whole reign, but the second founding as Byzantion, Polis Euxinos is regularly highlighted as the division between the Early Hellenistic Period of the World Empire from the First Golden Hellenistic Period - as much as that may have just been spite from Phillip III (OOC : Not the same one as OTL) at his cousins arrogance.

The Early Hellenistic was almost entirely dominated by the realignment of the World Empire around the Eastern Mediterranean and Black Seas, which wasn't exactly something done willingly. You mention the weakness of Darius III, but we have to remember the sheer power the Satraps had accumulated at that point. It was almost entirely Macedonian and Thracian armies that smashed the Satrapies of Artaxerxes IV, not any of the Western Satrapies or Egyptian forces - and that rebellion was arguably more powerful than Darius III was.

As much as the Alexandrian Line may have conquered the Empire, it was the Pontus-Phillipi Line that reformed it and kept it together.

OOC : The World Empire is what I see this Empire being called - combining Alt-Alexanders conquests with Alt-Alexander IVs conquest of Persia, and its successions. Basically Super-Persia but not exclusively Persian, sort of a "Western China" idea combining the Med, Arabian, South Russian and Persian regions.
 
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