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The Coming Day of the Lord (14:1-21)
The final chapter of the Book of Zechariah is an extended symbolic picture of the coming Day of the Lord. It begins with a description of the terrors accompanying the coming day (Zechariah 14:1-5) , describes briefly the security of "that day" (Zechariah 14:6-11), returns to describe the initiatory plague and panic (Zechariah 14:12-15), and concludes with details of the future blessedness (Zechariah 14:16-21).
Before the final blessedness Jerusalem will be captured by nations assembled in battle against her, and half her people will be taken into exile. Then will the Lord fight, standing on the Mount of Olives with such earth-shattering effect that a wide cleft will be created east of Jerusalem. Into this cleft God will come, accompanied by "all the holy ones." This picture of the final battle over Jerusalem (parallel to the account given in Zechariah 12:1 to Zechariah 13:6, but entirely different in detail) contemplates the actual personal participation of the Lord in the ancient manner of such battles as Megiddo (Judges 5:4), Mizpah (1 Samuel 7:10), and others.
The prophecy looks forward to a time of "neither cold nor frost" but of continuous day (Zechariah 14:6-7). Neither the intense daylight of the Near East (with its heat) nor the damp and chilly night, but a condition like evening with its delightful breezes will continue all the time. A year-round source of waters will flow out of Jerusalem, dividing to east and to west (Zechariah 14:8). No ritual purpose is served by this spring (unlike that in Zechariah 13:1).
The Lord will be recognized as King over all the earth, and no other will be worshiped at all (Zechariah 14:9). The prophecy contemplates the full acceptance of the ancient creed of Deuteronomy 6:4 by all peoples.
The geography of the Holy Land will be made over: from Geba, the northernmost town in Judah (near Bethel, as in 2 Kings 23:8), to Rimmon, probably near Beer-sheba, the land will be a plain except for the lofty plateau on which Jerusalem will be situated (Zechariah 14:10-11). Jerusalem shall dwell securely without fear of the threat of utter destruction in warfare.
Horrible plagues will befall the enemies of Jerusalem, if any are so foolhardy as to risk war against the divinely protected city. Disease and panic will overtake both men and animals, but the wealth of the nations will be collected — evidently as the spoil was left after the Syrians fled from Samaria (11 Kings 7:3-15). The mention of Judah fighting against Jerusalem is a discordant note suggesting a persistent feeling of rivalry (found also in Zechariah 12:2-5).
After the battles the survivors from other nations will come to Jerusalem to keep the Feast of Booths (Zechariah 14:16-19). This somewhat mechanical observance is viewed as the condition for rain upon their fields, except for Egypt which, being fertilized by the Nile, must be threatened with some other plague. The Feast of Booths (or Tabernacles) is important in this context not merely as the thanksgiving or harvest festival, but because it was the feast looking forward to the winter rains which were essential to the agricultural well-being of Palestine. It was also probably the occasion for the recognition of God as King over his people, and is thus appropriately connected with the recognition of the reign of God over all nations.
The prophecy clearly intends that everything in Jerusalem will be "holy to the Lord" (Zechariah 14:20-21). The Holy City will all be one holy area devoted to the worship of the Lord; the people will be free to use any available pots in boiling the sacrificial meal; no business transaction ("trader in the house of the Lord") will be needed to secure the necessary holy equipment for the performance of the ritual.
Like the oracle of Zechariah 12:1 to Zechariah 13:6, this final oracle of the Book of Zechariah looks forward to the day of God’s victory over the enemies of his people and to the consequent blessings and privileges to be enjoyed by the inhabitants of Jerusalem. When we realize that the prophet was expressing the deep longings of frustrated and discouraged people living in a time when God seemed far away, we may understand his effort to sketch the conditions in which God would be very real and vital in the life of the faithful community. Our task is to make our common life "holy to the Lord" in the midst of our particular frustrations and to be aware of his rule over all things.
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"Commentary on Zechariah 14". "Layman's Bible Commentary". https://www.studylight.org/
the Week of Proper 15 / Ordinary 20