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Zechariah 9:5

Adam Clarke
Bible Commentary

Ashkelon shall see it, and fear - All these prophecies seem to have been fulfilled before the days of Zechariah; another evidence that these last chapters were not written by him.

Her expectation shalt be ashamed - The expectation of being succoured by Tyre.

Albert Barnes
Notes on the Whole Bible

Ashkelon shall see and fear - The words express that to see and fear shall be as one. The mightiest and wealthiest, Tyre, having fallen, the neighbor cities of Philistia who had hoped that her might should be their stay, shall stand in fear and shame. Tyre, being a merchant-city, the mother-city of the cities of the African coast and in Spain, its desolation caused the more terror Isaiah 23:5-11.

And the - (a)

d king shall perish from Gaza - that is it shall have no more kings. It had been the policy of the world-empires to have tributary kings in the petty kingdoms which they conquered, thus providing lot their continued tranquil submission to themselves. The internal government remained as before: the people felt no difference, except as to the payment of the tribute. The policy is expressed by the title “king of kings,” which they successively bore. Sennacherib speaks of the kings of Ascalon, Ekron and Gaza.

A contemperary of Alexander mentions, that the king of Gaza was brought alive to Alexander on its capture. Alexander‘s policy was essentially different from that of the world-monarchs before him. They desired only to hold an empire as wide as possible, leaving the native kings, if they could; and only, if these were intractable, placing their own lieutenants. Alexander‘s policy was to blend East and West into one.. These petty sovereignties, so many insulated centers of mutual repulsion, were essentially at variance with this plan, and so this remnant of sovereignty of 1,500 years was taken away by him, when, after a siege in which he himself was twice wounded, he took it. Alexander wholly depopulated it, and repeopled the city with strangers.

And Ashkelon shall not be inhabited - Ashkelon yielded at once to Jonathan, when he “camped against it” (Judges 14:19. Commentators have assigned reasons, why Samson might have gone so far as the maritime Ascalon, whereas, in fact, he went to a city close by.

That city, in 536 a.d., had its Bishop.: “The site shows the remains of an early Christian Church or convent:” as a great lintel of stone, resembling somewhat the Maltese Cross, lies on the ground.” It was probably destroyed by the inundation of Muslim conquest. In 1163 a.d. it was a ruin. The distance of the ruins from the Ascalon Maiumas corresponds to that assigned by Benjamin of Tudela, being twice the distance of that city from Ashdod; but since he was at Beth Jibrin, he must have been not far from the spot where it has been recently discovered. The Ashkelon, which was Herod‘s birth-place and which he beautified, must have been the well-known city by the sea; since the distance from Jerusalem assigned by Josephus is too great for the old Ashkelon, and he speaks of it as on the sea.

Matthew Henry
Concise Bible Commentary
Here are judgements foretold on several nations. While the Macedonians and Alexander's successors were in warfare in these countries, the Lord promised to protect his people. God's house lies in the midst of an enemy's country; his church is as a lily among thorns. God's power and goodness are seen in her special preservation. The Lord encamps about his church, and while armies of proud opposers shall pass by and return, his eyes watch over her, so that they cannot prevail, and shortly the time will come when no exactor shall pass by her any more.
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