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> if Philip II was so smart, why was it Alexander who became Lord of Asia and not him? … So much for the pragmatic genius.

Phillip II went from captive in Thebes to overlord of Greece. In Ancient Greece where there were many small city-states this involved a lot of gaining control 1 by 1, via diplomacy and war. This takes a long, long time. About 23 years, as it turns out.

> Did Philip even have the ambition or desire needed to conquer Persia?

Of course he did. He founded a pan-Hellenic league and installed himself as its leader. The League of Corinth’s first act was to declare war against Persia. He had a large Macedonian force already in Asia Minor when he died. The invasion of Persia was already underway when Phillip died.

> Would he have had the tolerance needed to actually rule these areas that Alexander demonstrated (i.e. marrying Roxane despite it upsetting "old guard" generals, keeping in place a lot of the local government structures/making deals with people like Porus) or would he have insisted on violent rule that would have created conditions ripe for rebellion?

Marrying someone to establish an alliance was a day one strategy for Phillip II. Macedonian royalty were expected to have multiple wives. Phillip never insisted on brutality when he could have his way peacefully. Considering Alexander was the one who leveled Thebes I don’t really think setting up a wise, peaceful son vs violent, foolish father archetype is accurate.

[costco]

OK I was wrong in some respects. Philip was undoubtedly very smart. I guess my broader point is that planning to do it and actually doing it are different things. Like Alexander sieged Tyre which was pretty much thought to be impossible. Meanwhile there were much more familiar cities that Philip failed to siege and had to abandon.

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I’d recommend learning a lot more. For example, Phillip was actually an innovator in siege equipment and was the first person in Greece to really take towns by besieging them. You can count on two hands all the times in Greek history before Phillip where a city fell without the help of people inside the city betraying it. After, this changed a lot. Phillip probably wouldn’t have taken Tyre - but you forget that the only reason Alexander decided to take Tyre was because Tyre had surrendered but wouldn’t allow Alexander to come into the city for a religious festival honoring Heracles. I don’t think Phillip would have gone the same route.

[costco]

> So Alexander likely inherited a fully-formed invasion plan as well, though I suspect it only went as far as detaching western Asia Minor from the Achaemenids, not the whole empire.

And upon rereading, the article says this as well which is more along the lines of what I have read previously and what I meant about ambition. Would Philip have actually conquered the whole thing?