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Zechariah, like Revelation which draws on it, is a tough nut to crack but very rich. In the twelfth chapter, the prophet records the word of Yahweh that

The sorrow and mourning in Jerusalem on that day will be like the great mourning for Hadad-rimmon in the valley of Megiddo. —12:11 (NLT)

Is it known historically who Hadad-rimmon was, what led to his demise, and how he was mourned? Is there apocalyptic significance to the reference to Megiddo? Was this an event well-known in the ancient world?

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Clearly this mourning was apocalyptic and referred to the national mourning the spiritual Jerusalem would engage in upon the birth of the church during Messianic days. Even ancient references in the Talmud interpret Zechariah 12:10,12 as applied to the Messiah (according to Alfred Edresheim the Jewish historian in his book, The Life and Times of Jesus the Messiah, p. 1261). Some of which even identified this mourning with the death of Messiah. The 'mourning' would be like a great national mourning that gripped everyone, like experienced by the death of Josiah, who was slain at Hadadrimmon (a city) in the valley of Megiddon. This makes solid sense as Josiah was the last hope of the declining kingdom.

Although most translations say ‘of Hadad-rimmon’ and not ‘for’ as it was probably a city not a person, some do not take it as a city but as 'two' great lamentations of Israel. The one about the rock Rimmon and the other in the valley of Megiddo, for the death of Josiah. Some also understand Hadadrimmon to be the name of an 'actual man' who slew Ahab representing the first mourning and the second mourning still being for Josiah who Pharaoh Necho slew in the valley of Megiddo. In any case, it does not matter as it is simply referring to a great mourning irrespective of which exact one. I think the main idea is to connect the mourning with Josiah as he was a good King, and a mourning for Ahab seems improper for he was a wicked King and mourning for his idolatry is not fitting to the context. Mourning for a man who was not Jewish is hardly fitting at all. See Gill's Exposition of the Entire Bible on this verse here for this and other views about Hadad-rimmon.

Regarding names, various sources suggest the name Hadadrimmon comes from the joining of two Syrian idols: Rimmon and Hadad who was the idol of the sun. The meaning of this does not seem to have any relations to the current context, other than that idolatry was connected to the fall of Israel. However, specific to your question I have not encountered any speculation regarding the meaning of Megiddo. Yet looking up the Hebrew meaning I noticed (one meaning) for the Hebrew word Megiddo is "place of crowds". This may indicate that when Messiah would be pierced, in verse 10, It would not be done in a secret place, but in the centre of the world upon a stage, in front of a crowd. Not only so but as the world has looked and watched this past event, more than any other event in history, possibly we are part of Megiddo?

What seems counterintuitive about this verse is that it follows the ‘pouring out’ of ‘grace’ and ‘supplication’ in verse 10. One may think then that what should follow is praise and joy, not mourning. However in fulfillment when Messiah was ‘pierced’ for their transgressions (John 19:37) spiritual Israel (those who had faith like Abraham) were blessed by 'mourning'. For Jesus started his earlier sermons saying that, ‘blessed are they that mourn for there is the kingdom of heaven.’ (Mathew 5:4). There seems to be a direct connection.


Therefore it seems that in the days of Messiah a wonderful blessing would occur in the house of Israel, part of which would be great grace and mourning coupled with the view of a Messiah being ‘pierced’ and resulting in a new heavenly resurrected Israel of fantastic proportion and power. Possibly done in a kind of 'Megiddo', that is a valley before the crowd. The jeering arrogance of his persecutors was like a vantage point from which they would witness his suffering in an infinitely ‘low depression’ where he bore the weight of the world’s sin.


This may have presented a more immediate comfort and preliminary fulfillment to Israel under the Maccabees when they valiantly fought off invasions against Israel after the captivity but the situation of that day has little resemblance of the glorious description of Israel in these verses.

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Verse 11:

ביּום ההוא  יגדל המספּד בירוּשלם  כמספּד הדדרמון  בבקעת מגדון

In that day will become big the-lament in Jerusalem, like/as/akin-to haddadrimmon lament, in valley of megedon.

ביּום ההוא
In-day of the-that
(i.e. in that day)

יגדל המספּד
will-grow-big/will-increase the-lament

כמספּד הדדרמון
like haddadrimmon lament

בבקעת מגדון
in-valley of Meggido

Haddad was the god of agriculture/fertility. Or could it be one of the Palestinian/Philistine characters in the Bible?

Nobody knows what rimmon refers to. Everyone speculates. Meggido is a lush fertile valley in the Galilee lake region. Rimmon could be a settlement/village in that region. Then what is Haddad-Rimmon? May be Rimmon is a town populated by Haddad believers. During Zechariah's time, after the Israeli return from exile, there were still pagan populations in the region.

Like saying, "The Rome-Christian", rather than just saying "Rome".

Wikipedia indeed identifies a town Rimmon but is not in the Meggido/Galilee region, but west of the Dead Sea in south-central Israel. Whereas Galilee is in northern Israel.

Rimmon in Hebrew is pomegranate. The pomegranate is also a symbol of reproductive fertility. And so Hadad-Rimmon may be describing the fertility sect/denomination of the fertility god cult. But pomegranate is also used for symbolizing pregnant and fertile earth. So Hadad-Rimmon could refer to a sect of Haddad devotees whose mascot of religion is the pomegranate (like the cross (or fish) is the mascot of Christianity).

Like trying to differentiate the "Cross-Christians" from the "Fish-Christians". Or Baptists from Lutherans.

I would urge archaelogists to look for symbols of pomegranate among the artifacts of Haddad's religion and look for archaic fragments documenting lamenting among his devotees. That would give weight to my hypothesis.

כְּמִסְפַּד הֲדַדְרִמּוֹן

haddadrimmon lament

Is it possible that the haddad-rimmon lament was a huge, pagan, noisy, mournful festive rite? And those Haddad devotees of the Rimmon mascot are crying, beating themselves, yelling, and begging their fertility god for rain and a rich harvest and plentiful children they could use as cheap labor?

Is the verse saying ..

On that day, the lament in Jerusalem will become huge, like those annoying noisy dreadful rites by the Hadad devotees of the Pomegranate persuasion in the Meggido valley. (So Jerusalem too will mourn like that.)

Oh, so you despise and mock those loud ululating cries huh, but you Jerusalem and house of David will too ulalate like that in despair.

Verse 10:

OK, let's look at verse 10.

ושפכתי על בית דויד ועל יושב ירושלם 
רוח חן ותחנונים
והביטו אלי
את אשר דקרו
וספדו עליו
כ מספד 
על ה יּחיד
וְהמר עליו
כהמר על הבכור

And I will pour on the house of David and the inhabitants of Jerusalem
The spirit of grace and supplication
And they will look at me
you whom they pierce
And/but they will mourn on/over him
Like mourning
On/over the only one 
And feel-bitter on/over him
Like feeling-bitter on/over the first-born

Interpretation 1

And I will pour on the house of David and the inhabitants of Jerusalem
The spirit of grace and supplication
And they will look at ne
And you (Zecharia) they (the house of David and the inhabitants of Jerusalem) will pierce
But they will mourn over him (the one being pierced)
Like mourning the only begotten
And they will feel bitter over him (the one being pierced)
Like feeling-bitter over the first born

Interpretation 2

And I will pour on the house of David and the inhabitants of Jerusalem
The spirit of grace and supplication
And they will look at me
And you (an unnamed entity) they
  (the house of David and the inhabitants of Jerusalem) will pierce
But they will mourn over him (the one being pierced)
Like mourning over the only begotten
And they will feel bitter over him (the one being pierced)
Like feeling-bitter over the first-born

The passage does not say

mourning for the only begotten

or

being bitter for the first-born.

Rather it says,

Mourning and being bitter for an unspecified entity LIKE anyone WOULD for an only begotten or for a first-born.

Does the unnamed entity in signify a messiah? Or Zechariah himself? Or a non-messianic person?

The Hebrew in the Bible sometimes (often?) switches between the indirection of the noun. Is the "he" and "you" the same person?

Like in the 23rd Psalm, the author starts off with referring to the LORD in the 3rd person singular

The LORD is my Shepherd and I shall not be in want. He ....

and then abruptly switches to using the 2nd person

Your sceptre and your staff, they comfort me ...

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I'm giving the bounty to you since you obviously worked hard on this answer. I appreciate that. However, it's become a little bit disjointed. I kinda got lost in the middle somewhere, so I'm going to take a crack at editing it a bit. Thanks again for the answer! –  Jon Ericson Jul 10 '12 at 22:15
    
Thanks for the award. (Also thank you for changing my British spelling to US spelling. I am very used to writing in British style.) I think I made a mistake on the word את. I mistakenly presumed it was the pronoun you. I think it is more appropriately the accusative preposition which is used regardless of indirection and quantity. So the phrase should be translated "at the one whom they pierce". –  Blessed Geek Jul 12 '12 at 9:02
    
No problems. (I shouldn't have changes British to US spelling--either is fine. It was force of habit, I think. ;-) I see that your edit pushed this post into community wiki. I'll fix that for you. Again, thanks for the effort you put into this answer. –  Jon Ericson Jul 12 '12 at 15:40
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"see that your edit pushed this post into community wiki" - what is that? I have always wondered what/how "community wiki". –  Blessed Geek Jul 23 '12 at 16:33
1  
The mechanism was inherited from Stack Overflow, which is an extremely different site than our own in terms of subject matter. You aren't the only person to be confused by this, rather strange feature. –  Jon Ericson Jul 23 '12 at 16:44
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like the mourning of Hadadrimmon in the Valley of Megiddon: Hadadrimmon has no connection to the Valley of Megiddon. These are, rather, two cases of mourning. [The first is] like the mourning of Ahab the son of Omri, who was slain by Hadadrimmon the son of Tabrimmon in Ramoth Gilead, as it is stated (I Kings 22:36): “A cry passed through the camp.” That is the mourning [of Ahab. The second case is] like the mourning of Josiah the son of Amon, who was slain by Pharoah the lame in the Valley of Megiddon, as it is stated (II Chron. 35:25): “And Jeremiah lamented for Josiah, and all the singing men and singing women spoke in their laments, etc.”

-Rashi

Implicit in Rashi's interpretation is that even though there were two events, the author treats them as one.

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+1 helpful answer. –  Kazark Jul 4 '12 at 16:32
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