5 Ashkelon shall see it and fear; Gaza also shall be very sorrowful; And Ekron, for He dried up her expectation. The king shall perish from Gaza, And Ashkelon shall not be inhabited. 6 “A mixed race shall settle in Ashdod, And I will cut off the pride of the Philistines. 7 I will take away the blood from his mouth, And the abominations from between his teeth. But he who remains, even he shall be for our God, And shall be like a leader in Judah, And Ekron like a Jebusite.
In verses 5-7, Zechariah listed four of the five capital cities of Philistia, which were called the Pentapolis. Gath was not mentioned because it was incorporated into Judah during the time of Alexander’s invasion.
These four cities here were Philistine. This section shows Alexander’s march along the Mediterranean Sea from Phoenicia into Philistia.
Ashkelon shall see it and fear;
Ashkelon was a commercial seaport on the Mediterranean.
Gaza also shall be very sorrowful;
Gaza was a trade center located on the Mediterranean shore 40 miles south of Jaffa. Alexander’s army slaughtered ten thousand citizens. Those who remained were sold into slavery.
And Ekron, for He dried up her expectation.
Ekron was in northern Philistia 35 miles southwest of Jerusalem. This city probably expected Tyre to stand against Alexander.
The king shall perish from Gaza,
After Ekron’s defeat, king Betis was bound to a chariot by thongs pierced through his feet and then dragged through the city until he died.
And Ashkelon shall not be inhabited.
Alexander devastated Ashkelon to the degree that it could not be inhabited.
“A mixed race shall settle in Ashdod, And I will cut off the pride of the Philistines.
The “pride” of the Philistines was their commercial wealth. Few people remained after the city’s devastation. It had to be repopulated with a mixed race. Speaking to Zechariah in the first person, the Lord said that He would transform the Philistines for Himself.
I will take away the blood from his mouth, And the abominations from between his teeth.
The “blood” here refers to heretical animal sacrifices, as the word “abominations” often means the heresy of idol worship.
But he who remains, even he shall be for our God, And shall be like a leader in Judah,
As Hamath, Damascus, and Tyre turned to God, so the Philistines would do the same. Some would even govern Judah.
And Ekron like a Jebusite.
Jebusites were a tribe in Jerusalem (Jebus) before David conquered the city in 1004 BC. The Jebusites were absorbed into the population of Israel. The Messiah will defeat this city in His Millennial kingdom (Zech 9:10).
The Messiah will be a world Conqueror.
The first eight verses describe Alexander’s victory over the enemies of Israel in Syria to the north and Phoenicia to the east. All these enemies would be defeated by Alexander the conqueror.
In 332 BC, Gaza resisted Alexander, but he conquered the city in five months. One day the Messiah Himself will conquer the entire world and be its Sovereign.