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This question has bothered me on and off over the years - typically around this time as we read this perek on the first day of Sukkot as the haftarah:

וְעָמְד֣וּ רַגְלָ֣יו בַּיּוֹם־הַ֠הוּא עַל־הַ֨ר הַזֵּתִ֜ים אֲשֶׁ֨ר עַל־פְּנֵ֥י יְרוּשָׁלִַם֮ מִקֶּדֶם֒ וְנִבְקַע֩ הַ֨ר הַזֵּיתִ֤ים מֵֽחֶצְיוֹ֙ מִזְרָ֣חָה וָיָ֔מָּה גֵּ֖יא גְּדוֹלָ֣ה מְאֹ֑ד וּמָ֨שׁ חֲצִ֥י הָהָ֛ר צָפ֖וֹנָה וְחֶצְיוֹ־נֶֽגְבָּה׃

On that day, He will set His feet on the Mount of Olives, near Jerusalem on the east; and the Mount of Olives shall split across from east to west, and one part of the Mount shall shift to the north and the other to the south, a huge gorge.

My question (several, actually) is: if this nevuah is to be taken at face value what will happen to those buried on Har haZeisim when this dramatic cleaving occurs? Again, if this is the literal understanding of the verse (and my impression from the commentaries is such that it is) then when and who allowed the usage of Har haZeisim as a burial place at all?

If anyone has insights or better yet references with whom to consult I'd greatly appreciate it.

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    According to Wikipedia, this Nevuah is part of the 'Techias Hameisim' process. So according to that, the answer to your question is that those buried there will be rising there, and this 'dramatic cleaving' is done there specifically because there are dead buried there. en.wikipedia.org/wiki/Mount_of_Olives#Burial_and_resurrection – Salmononius2 Sep 26 '18 at 19:13
  • Milchemes Gog u'Magog, which is the topic of this chapter in Zecharia, precedes Techias HaMeisim, IIRC. Also, the split of the mountain is for two purposes, according to most commentaries: 1) so that the Jews endangered by Gog's approach can escape through the breach, and 2) so that the referenced gushing of water can run through the breach as well. – Shmuel Brown Sep 26 '18 at 19:26
  • @ShmuelBrown The assumptions being made by both of you are where the difficulty lies. Why were the books of the Prophets chosen for inclusion by Ezra? Because they apply to each and every generation. Unless you assume Zechariah is literal in every generation, you must say it contains to a large extent, allegory. And a given detail that is literal for 1 generation is allegorical for the next. More than that, in a given generation, 1 detail may be allegorical and the next detail literal. It’s not all literal or all allegorical for the vast majority. – Yaacov Deane Sep 26 '18 at 22:48
  • Additionally, your assumptions about resurrection are also incorrect. We know from Daniel and elsewhere that resurrection has many different time periods. Similarly, the war of Gog u’Magog has at least 3 distinct parts mentioned in Tanach. What applies to one part, needn’t apply to another. – Yaacov Deane Sep 26 '18 at 22:53

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