Albert Barnes Commentary Zechariah 9:5

"Ashkelon shall see it, and fear; Gaza also, and shall be sore pained; and Ekron, for her expectation shall be put to shame; and the king shall perish from Gaza, and Ashkelon shall not be inhabited." — Zechariah 9:5 (ASV)

Ashkelon shall see and fear - The words express that seeing and fearing will be as one. The mightiest and wealthiest, Tyre, having fallen, the neighboring cities of Philistia, which had hoped that her might would be their support, will stand in fear and shame. Tyre, being a merchant city—the mother city of the cities on the African coast and in Spain—its desolation caused greater terror (Isaiah 23:5–11).

And the king shall perish from Gaza - that is, it will have no more kings. It had been the policy of the world empires to have tributary kings in the petty kingdoms they conquered, thus providing for their continued tranquil submission to themselves. The internal government remained as before: the people felt no difference, except for the payment of 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 contemporary of Alexander mentions that the king of Gaza was brought alive to Alexander upon 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 in place if they could, and placing their own lieutenants only if these kings proved intractable. Alexander’s policy, in contrast, was to blend East and West into one.

These petty sovereignties, being so many insulated centers of mutual repulsion, were essentially at variance with this plan. Therefore, this 1,500-year remnant of sovereignty was taken away by him when, after a siege in which he himself was twice wounded, he captured 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” , after he had taken and “burned Ashdod and the cities round about it.” In another expedition of Jonathan, its inhabitants “met him honorably,” while “they of Gaza shut him out” at first (1 Maccabees 11:60, 61). “Simon passed through the country to Ascalon, and the strongholds there adjoining,” without resistance, whereas “he turned aside to Joppa, and won it” .

He placed Jews in Gaza, but of Ascalon nothing is said. The ruins of a Christian city built on its site, “Khirbet-Ascalon,” have recently been discovered in the hills near Tell Zakariyeh, and so, a little south of Timnath, a Philistine city in the days of Samson, from which Samson went to it to gain the thirty changes of raiment (Judges 14:19). Commentators have assigned reasons why Samson might have gone as far as the maritime Ascalon, whereas, in fact, he went to a city close by.

That city, in A.D. 536, had its Bishop. It is recorded: “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 wave of Muslim conquest. In A.D. 1163, it was a ruin.

The distance of the ruins from 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 recently been discovered.

The Ashkelon that was Herod’s birthplace 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 being on the sea.