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Why the Mount of Olives?
At the conclusion
of His ministry to Israel, the Lord Jesus Christ chose to formally ascend to His Father, to be our Intercessor, from the Mount of Olives; not from the Upper Room.
before this, Zechariah had prophesied that it would be to this same Mount of Olives to which God would come in power at the end to delivery Israel from annihilation and inaugurate His kingdom –
• In the original Hebrew:
ויצא יהוה ונלחם בגוים ההם כיום הלחמו ביום קרב׃
ועמדו רגליו ביום־ההוא על־הר הזתים אשׁר על־פני ירושׁלם מקדם ונבקע הר הזיתים מחציו מזרחה וימה גיא גדולה מאד ומשׁ חצי ההר צפונה וחציו־נגבה׃
• In the Jewish Septuagint Greek:
καὶ ἐξελεύσεται κύριος καὶ παρατάξεται ἐν τοῖς ἔθνεσιν ἐκείνοις καθὼς ἡμέρα παρατάξεως αὐτοῦ ἐν ἡμέρᾳ πολέμου.
καὶ στήσονται οἱ πόδες αὐτοῦ ἐν τῇ ἡμέρᾳ ἐκείνῃ ἐπὶ τὸ ὄρος τῶν ἐλαιῶν τὸ κατέναντι Ιερουσαλημ ἐξ ἀνατολῶν· καὶ σχισθήσεται τὸ ὄρος τῶν ἐλαιῶν, τὸ ἥμισυ αὐτοῦ πρὸς ἀνατολὰς καὶ τὸ ἥμισυ αὐτοῦ πρὸς θάλασσαν, χάος μέγα σφόδρα· καὶ κλινεῖ τὸ ἥμισυ τοῦ ὄρους πρὸς βορρᾶν καὶ τὸ ἥμισυ αὐτοῦ πρὸς νότον. (LXX)
• In today's English:
"Then the LORD (יהוה/YHWH/Jehovah) will go out and fight against those nations as when He fights on a day of battle.
On that day His feet shall stand on the Mount of Olives that lies before Jerusalem on the east,
and the Mount of Olives shall be split in two from east to west by a very wide valley,
so that one half of the Mount shall move northward, and the other half southward."
– why this Mount of Olives?
Zechariah 14:3-4

it would have made much more sense for Christ to conclude His ministry and ascend from the Upper Room, where He had attested His resurrection to His apostles, and the place where, ten-days later after His ascension, the Holy Spirit would be given to the waiting disciples on the morning of Pentecost?
Why choose another place, and one which put His disciples at more public risk of arrest.
are truths in Holy Scripture which are not foundational – but, for those with spiritual appetite, they lead into a deeper appreciation of the Most High and His awesome ways with humanity.
The sign-post to the answer of this question is given to us in 2 Samuel 15:30-32. Many translations are not very accurate in portraying the tense of the grammar in the text here, but the Jewish Publication Society translation is fairly accurate –
"...David went up by the ascent of the Mount of Olives...
 And it came to pass, that when David was come to the top of the ascent, where God was wont to be worshipped..." 
Many translations try and interpret this as a worship act of David but that is simply not true to the tense of the holy text.

is of King David, before any temple had been built in or near Jerusalem, evacuating his troops from the city as he prepares to defend his rulership against the attack of his rebellious son Absalom. Just in passing, the holy text mentions (and every word is inspired of God) that the place on the Mount of Olives where David was standing at that time was the place where God had previously been worshipped; previous to David's time. By whom?
Before David became Israel's king, Jerusalem had not even been a city of Israel. It was a Jebusite stronghold which he conquered and made his capital. Most scholars teach that he made it his capital because of its strategic central location but this is not true. Jerusalem was not on any main route and did not control any strategic area, but it had been the city of the godly Melchizedek in the time of Patriarch Abraham.
is only one possible significance, if the Bible is true, concerning a place on the Mount of Olives at which the Most High was worshipped before David's time: that is of king Melchizedek (מלכּי־צדק/righteous king) leading his Amorite people in worship of God Most High (El Elyon/אֵל עֶלְיֹון), at that place, a character of leadership
which had earned that city the name Salem, Peace, which continues forever in the name Jeru-salem.
The Mount of Olives is eastward (in front...) of Jerusalem and higher than the city so it receives the first light of each new day. The ancient peoples (in ancient Egypt) often built their temples facing the rising sun for its symbolism and this continued, by God's instruction, in both the Tabernacle of Moses and the later Temple of Solomon. It would have been understandable therefore that this eastern mount, higher than the city itself, would have been the preferred open-air public worship venue of the people of Melchizedek at a time when open-air sanctuaries were the norm in that region, as Abraham had practiced at both Shechem and Mamre in the Amorite sanctuaries of that time.
later, after Israel had turned away from God in following their prosperity and fertility idols, the prophet Ezekiel sees in symbolic vision the departure of the Glory of the Lord from Israel's temple. Note then where that Glory lifted from the temple and came to rest in his prophetic revelation. . .
"And the Glory of the Lord went up from the midst of the city,
stood on the mountain which was in front of
(east of) the city"
The Mount of Olives!

Ezekiel 11:23
awesome significance of this perspective in Holy Scripture however, is that a particular 'place', to which neither Israel's religion or military history attached any significance whatsoever, is chosen by God to be the one place on this planet from which the Christ of God returns to Heaven and in the future to be the same place to which the Christ of God will return in glory at the climax of this age
after having lifted His people into His own resurrection to share His rule over all – forever.
Praise God for the faithfulness of Melchizedek, before any book of the Bible was written, and before Israel had come into existence – for his loyalty to the knowledge of "God Most High, Maker of heaven and earth"!
And so to him therefore, God is likewise loyal...
From the mouth of Melchizedek (Gen.14:19) which Abram echoed (14:22).
If God
continues loyal to this extent, to someone like an Amorite king Melchizedek, then what it not within the capacity of God's people today to demonstrate the faithfulness of this same 'God Most High, Make of Heaven and Earth' to all generations in every place, for God does not despise the capacity and the limits of those who seek to serve Him?   Hallelujah!

For Melchizedek's Sake The Jerusalem Works of Jesus Israel's Right to Canaan Common 'Christian' Fallacies

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