In verses 5-8 the focus shifts from nations to the north to a nation to the west, namely the Philistines. Four of their five main centers are mentioned; the fifth, Gath, had been destroyed by the Assyrians in 711 B.C. These cities are pictured as being thrown into panic by observing the fate of Tyre, apparently their ally. In terms of structure, it is noteworthy that the first three cities are mentioned in a chiastic order Ashkelon-Gaza-Ekron-Gaza-Ashkelon. This pattern puts a focus on Ekron, the one at the turning point, so it is no surprise that Ekron is the one mentioned again in verse 7, where it seems to stand for the Philistines as a whole. The same four cities are mentioned in Amos 1.6-8 and Zeph 2.4, but in a different order.
Ashkelon shall see it, and be afraid: By a figure of speech called metonymy, Ashkelon (and indeed the other city names) stands for the inhabitants of the city. In certain languages it will be necessary to do away with this figure of speech and say, for example, “The people of Ashkelon will see it and be afraid.” There is another example of alliteration between the Hebrew words for see (tereʾ) and be afraid (tiraʾ). The Hebrew contains no equivalent to it (“this” in Good News Translation), which is included in English to make the flow of thought clearer. It refers of course to the fall of Tyre in the previous verse.
Gaza too, and shall writhe in anguish: The verb translated writhe in anguish refers to the pains of childbirth. Good News Translation “suffer great pain,” and modern versions generally, lose this figure. However, in many cultures it may be possible to keep it, perhaps by turning the metaphor into a simile: “The people of Gaza will also see it, and suffer agony like a woman in labor.”
Ekron also, because its hopes are confounded: The word also seems to refer back to shall writhe in anguish in the description of Gaza rather than to shall see it in the description of Ashkelon. Thus the next clause because its hopes are confounded explains why Ekron will also writhe in anguish. What is not stated here, but must be understood, is that the Philistine cities were allied with Tyre, and relied on its strong fortifications to delay any invader coming from the north. If Tyre was captured, then the Philistine cities were also bound to fall, and their hope of escape was gone. The Hebrew word translated its hopes is found in the same sense of political and military reliance in Isa 20.5-6, where it refers to the reliance of Judah on Ethiopia and Egypt. Other ways to express this sentence are “The people of Ekron will also be in agony because they have lost hope” and “Ekron also will suffer greatly and despair because it no longer has the support of Tyre.”
The king shall perish from Gaza: Gaza was the largest of the Philistine cities. Losing its king meant losing its independence, and being swallowed up by some other stronger nation. Shall perish means “will be killed.” For king see Hag 1.1.
Ashkelon shall be uninhabited: The people will be killed, captured, or driven away, and the city of “Ashkelon will be left deserted” (Good News Translation), or “There will be no people left in Ashkelon,” or “Ashkelon [will be] emptied of its people” (Contemporary English Version). Compare Zeph 2.4.
Quoted with permission from Clark, David J. & Hatton, Howard A. A Handbook on Zechariah. (UBS Helps for Translators). New York: UBS, 2002. For this and other handbooks for translators see here .