Parmenion

Philip, planning his Asiatic war under the convenient banner of the Hellenic ‘crusade’ created by Isocrates and other intellectuals, sends to Asia Minor an advance force of the Macedonian army under Amyntas, a son of Philip's brother late Perdiccas, and generals Parmenio and Attalus (Parmenio's son-in-law) early in 336 BCE.

Philip's great general Parmenio, who had secured a foothold in Asia Minor during Philip's lifetime, commands the Thessalian cavalry on the left; many of the sixty-four-year-old warrior's family and supporters are entrenched in positions of responsibility.

In addition, there are lighter armed troops, such as the scouts, and less-coordinated but highly effective contingents of slingers and other irregulars, usually from the parts of Greece where the concept of polis is imperfectly developed.

This army is a formidable machine in the metaphorical sense.

There also are literal machines-stone-throwing siege engines that can be assembled on the spot.

The Thessalian siege engineers associated with Philip certainly continue into Alexander's reign (and will enable him to conquer Anatolia and Phoenicia at comparatively high speed, given the fortified obstacles confronting him).

Surveyors, engineers, architects, scientists, court officials, and historians accompany the army of Alexander, who, from the outset, seems to envisage an unlimited operation.

At Gordium in Phrygia, the old capital of the Phrygian kings (themselves, as stated above, ultimately of alleged Macedonian origin) tradition records Alexander’s “breaking” of the Gordian knot, or fastening, of an ancient chariot, which can only be loosed by the man who is to rule Asia; but this story may be apocryphal or at least distorted.

Alexander cuts it instead—or perhaps pulls out the pole pin, as one tradition insists.

At this point, Alexander benefits from the sudden death of Memnon of Rhodes.

From Gordium, …

…Alexander pushes on to Ancyra (modern Ankara), thence south …

…through Cappadocia and the Cilician Gates (modern Külek Bogazi).

Alexander is delayed for a time in Cilicia by a fever following his campaign through the Anatolian highlands, which had been meant to impress the tribesmen.

Achaemenid king Darius III, after a protracted delay, has meanwhile advanced with his Grand Army northward on the eastern side of Mount Amanus.

Greek mercenary leader Charidemus had been one of those whose surrender was demanded by Alexander the Great after the destruction of Thebes, but escaped with banishment and fled to Darius, who had received him with distinction.

However as Charidemus had expressed his dissatisfaction with the preparations made by the king just before the coming battle, he is put to death.

Intelligence on both sides is faulty, and in autumn 333 Alexander is already encamped by Myriandrus (near modern Iskenderun, Turkey) when he learns that Darius is astride his line of communications at …

…Issus, a plain on the coast, north of Alexander's position.

Turning, Alexander's Macedonian forces, greatly outnumbered by the Persians, with an infantry phalanx in the center and cavalry on the sides, find the army of Darius drawn up on the opposite bank of the Pinarus (either modern Payaz or Deli) River.

Alexander leads the charge across the river, shattering the Persian left wing before turning against the Greek mercenaries who form the Persian center; first isolated, they are then slaughtered.

Alexander's Companion cavalry punches a hole in the poorly trained Persian infantry, making straight for Darius himself, who takes flight, leaving behind much of his personal treasure.

Alexander’s troops pursue the Persians, killing one hundred and ten thousand of them and losing a total of three hundred and two from the Macedonian forces.

His army in confusion, Darius escapes, but his mother, Sisygambis, wife, and children are captured; the women are treated with chivalrous care.

Arrian claims a Macedonian loss of only four hundred and fifty men, with Alexander himself being wounded.

From Issus, Alexander marches south …

…into Syria and Phoenicia, his object being to isolate the Persian fleet from its bases and so to destroy it as an effective fighting force.

To Alexander, Palestine is, as to many before him, a corridor leading to Egypt, the outlying Persian province.

Consequently, in his attack on that province after the Battle of Issus, he confines his attention, in his passage southward, to reducing the coastal cities that might form bases for the Persian fleet.

The Phoenician cities Marathus and …

...Aradus come over quietly, and ...

...Parmenio is sent ahead to secure Damascus and its rich booty, including Darius' war chest.

In reply to a letter from Darius offering peace, Alexander replies arrogantly, recapitulating the historic wrongs of Greece and stipulating that, should Darius agree to recognize Alexander's claim to be lord of Asia and address him as such for the future, he can have his family back—“mother, wife, children, whatever you like.”

The offer is refused.