This begins the 3rd section in Zechariah, which deals with the coming of the Messiah. It covers the same ground as the visions but from a different viewpoint.
Zechariah 9:1 The burden of the word of the L-RD is against the land of Hadrach, with Damascus as its resting place (for the eyes of men, especially of all the tribes of Israel, are toward the L-RD),
“burden” means “judgment”
The ninth letter is “Tet” - serpent; objective good - that which appears evil but is for our improvement
“Alexander the Great” was G-d’s instrument of judgment.
This is history now but at the time it was written it was prophecy.
See our study on Daniel chapters 2, 7, 8, and 11 for more prophecy on the Greek Empire in prophecy.
As Alexander’s army swept east it attacked and destroyed what was in its path.
Zechariah 9:2-4 And Hamath also will border thereby; Tyre, and Sidon, though it be very wise. And Tyre did build herself a strong hold, and heaped up silver as the dust, and fine gold as the mire of the streets. Behold, the L-rd will cast her out, and he will smite her power in the sea; and she will be devoured with fire.
Tyre was an impregnable island fortress. Others had failed to take her. Alexander the Great used the ruins from the mainland and built a causeway out to the island. It took seven months to complete. This enabled his army to conquer the island.
Zechariah 9:5-6 Ashkelon will see it, and fear; Gaza will also see it, and be very sorrowful, and Ekron; for her expectation will be ashamed; and the king will perish from Gaza, and Ashkelon will not be inhabited. Foreigners will occupy Ashdod, and I will cut off the pride of the Philistines.
These cities listed here were in Israel and were also destroyed by Alexander the Great. The Philistines were destroyed and NEVER emerged as a nation again.
Zechariah 9:7 And I will take away his blood out of his mouth, and his abominations from between his teeth: but he that remains, even he, will be for our G-d, and he will be as a governor in Judah, and Ekron as a Jebusite.
This verse is referring to the polluted food and idolatrous sacrifices the Philistines engaged in. They will no longer worship idols but the true and living G-d.
Zechariah 9:8 And I will encamp about mine house because of the army, because of him that passes by, and because of him that returns: and no oppressor will pass through them any more: for now I have seen with my eyes.
G-d will protect Jerusalem from the evading Greek army.
Flavius Josephus in “The Antiquities of the Jews” Book XI, chapter VIII, p 350. Tells this story of Alexander the Great arriving in Jerusalem:
“And when he (the High Priest) understood that he (Alexander the Great) was not far from the city (Jerusalem), he (the High Priest) went out in procession with the priests and the multitude of citizens. The procession was venerable, and the manner of it different from that of other nations … and when the Phoenicians and the Chaldeans that followed him (Alexander the Great), thought that they should have liberty to plunder the city, and torment the high priest to death, which the king’s displeasure fairly promised them, the very reverse of it happened; for Alexander, when he (Alexander the Great) saw the multitude at a distance, in white garments, while the priests stood clothed in fine linen, and the high priest in purple and scarlet clothing, with his miter on his head, having the golden plate whereon the name of G-d was engraved, he (Alexander the Great) approached by himself, and adored that name (the name of G-d), and first saluted the high priest. The Jews also did altogether, with one voice, salute Alexander, and encompass him about; where upon the kings of Syria and the rest were surprised at what Alexander had done, and supposed him disordered in his mind (They thought Alexander was crazy for bowing before the High Priest). However, Parmenio alone went up to him (Alexander the Great) and asked him how it came to pass that, when all others adored him, he should adore the high priest of the Jews? To whom he replied, “I did not adore him, but that G-d who hath honored him with his high-priesthood; for I saw this very person in a dream, in this very habit (high priestly garment), when I was at Dios in Macedonia, who, when I was considering with myself, how I might obtain the dominion of Asia, exhorted me to make no delay, but boldly to pass over the sea thither, for that he (G-d) would conduct my army, and would give me the dominion over the Persians; whence it is, that having seen no other in that habit (high priestly garment), and now seeing this person in it, and remembering that vision, and the exhortation which I had in my dream, I believe that I bring this army under the divine conduct, and shall therewith conquer Darius, and destroy the power of the Persians, and that all things will succeed according to what is in my own mind.”
There is a tradition that says when the high priest met Alexander the Great outside Jerusalem that he took with him the book of Daniel and showed Alexander the prophecy concerning him. It is said that this so moved Alexander that he went to the temple to offer a sacrifice and worship G-d.
Zechariah 9:9 Rejoice greatly, O daughter of Zion! Shout in triumph, O daughter of Jerusalem! Behold, your king is coming to you; He is just and endowed with salvation, Humble, and mounted on a donkey, Even on a colt, the foal of a donkey.
This verse contrasts how Alexander the Great would enter Jerusalem to how the Messiah would enter.
“Salvation” - He came with “victory” over spiritual death and “deliverance” from the bondage of sin.
This verse was fulfilled during Yeshua’s first coming, when He came as the atonement for our sins.
Matt 21:1-5 As they approached Jerusalem and came to Bethphage on the Mount of Olives, Yeshua (Jesus) sent two disciples, saying to them, "Go to the village ahead of you, and at once you will find a donkey tied there, with her colt by her. Untie them and bring them to me. If anyone says anything to you, tell him that the L-rd needs them, and he will send them right away." This took place to fulfill what was spoken through the prophet: "Say to the Daughter of Zion, `See, your king comes to you, gentle and riding on a donkey, on a colt, the foal of a donkey.'"