Passage
Ashkelon shall see it, and fear; Gaza also shall see it, and be very sorrowful, and Ekron; for her expectation shall be ashamed; and the king shall perish from Gaza, and Ashkelon shall not be inhabited.
Zechariah 9:5 (KJV)
Nearby Context
Zechariah 9:3 And Tyrus did build herself a strong hold, and heaped up silver as the dust, and fine gold as the mire of the streets.
Zechariah 9:4 Behold, the LORD will cast her out, and he will smite her power in the sea; and she shall be devoured with fire.
Zechariah 9:5 Ashkelon shall see it, and fear; Gaza also shall see it, and be very sorrowful, and Ekron; for her expectation shall be ashamed; and the king shall perish from Gaza, and Ashkelon shall not be inhabited.
Zechariah 9:6 And a bastard shall dwell in Ashdod, and I will cut off the pride of the Philistines.
Zechariah 9:7 And I will take away his blood out of his mouth, and his abominations from between his teeth: but he that remaineth, even he, shall be for our God, and he shall be as a governor in Judah, and Ekron as a Jebusite.
Study Lenses
The verse centers on "ashkelon", "shall", "fear", "gaza", "very", "sorrowful", and "ekron". It is saying that the verse draws attention to "ashkelon" and "shall", so its meaning should be read from those terms before moving to application.
The nearby context moves from verse 4's "Behold the LORD will cast her out..." into verse 6's "And a bastard shall dwell in Ashdod...", so "ashkelon" and "shall" belong inside that flow. In Zechariah context, the local focus is covenant, worship, and faithfulness.
A plain takeaway is to answer the verse's own emphasis on "ashkelon" and "shall" with trust shaped by these words, not by a vague optimism outside the passage.