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Luke 19:44 They will not leave one stone on another, because you did not recognize the time of God's coming to you.

How does this relate to the standing Western Wall or Wailing Wall in the Old City of Jerusalem today?

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The prophecy of Luke 19:44b about "not leaving one stone upon another" could not be literally true for at least two reasons:

  • A few relics of structure remained after Titus had finished - there were only one or two towers and of course the wailing wall
  • Even if these structures had also been demolished, the rubble would still literally be stones upon another.

Jesus' words in this prophecy are clearly Hebrew hyperbole simply implying that the city was so demolished as to be unrecognizable. However, it was literally true of the temple itself as Titus plowed the field after demolishing the temple area. Note the comments of Barnes:

Shall lay thee even with the ground ... - This was literally done. Titus caused a plow to pass over the place where the temple stood. See the notes at Matthew 24. All this was done, says Christ, because Jerusalem knew not the time of its visitation - that is, did not know, and "would not" know, that the Messiah had come. "His coming" was the time of their merciful visitation. That time had been predicted, and invaluable blessings promised as the result of his advent; but they would not know it. They rejected him, they put him to death, and it was just that they should be destroyed.

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To understand Luke 19:44, you need to ‘add’ Mark 13 and Matthew 24 into the context. They are descriptions of the same event. And, they are Literal. But they relate to the Temple, not the ‘wall’.

Because they, the Jews, did not recognise the ‘visitation’ of the Messiah, that is, did not accept the Messiah, he would leave them. They rejected him, so he could no longer be their God - and protect them.

Yes these words came after the ‘triumphant entry’, and the people had adorned him as ‘king’, but nevertheless they (the leaders, speaking for the people.) had rejected him as Messiah.

Result - of no God - the Temple was demolished, every stone, in 70 AD. And the rest, persecution of the Jews ever since.

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From the outset of this answer I admit that it is based on a series of "what ifs" which may be difficult or impossible to prove- however, they may also be difficult or impossible to disprove.

Both Dave and Dottard have given answers which contain the word "temple". In the Greek there are two words for the one word "temple".

The hierou consisted of the temple precincts of courts, porticos and other constructs including the wailing wall.

The naon [Luke 1:9, Acts 7:48, Acts 17:24, 1 Cor 6:19] was the Holy place where only the priests were allowed to enter [though Judas may have forced his way in] and the Holy of Holies which was entered only on the great day of atonement by only the high priest.

What if the disciples [as per Mat 24:2] pointed out to Jesus the buildings of the hierou, but He looking at or pointing at [we are not told] the naon said "you see all these...they will all be thrown down" [words to that effect]?

What if the disciples said something to Him about one thing, the hierou, but Jesus came back at them not in their terms of beauty and magnificence but His warning of destruction. Not their idea, the hierou, but His idea, the naon?

What if "not one stone on another" means "not one stone on another as you see them now", or, "not as they were originally arranged"?

What if in 70 AD every stone of the naon was put out of place meaning that the heart of the old system was destroyed, but the precincts including the wailing wall only mostly destroyed?

If Judaism no longer having animal sacrifices in Jerusalem means that its heart has been ripped out, Judaism can still have vestiges intact; Jews are still living there and they connect to the wailing wall.

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Literal

People even today push dollar bills and gold coins into the cracks of the wall as a sort of "blessing".

Jesus saw them doing this and declared that this "blessing" would cause its destruction when war came.

Jesus sat down opposite the temple "treasury" where the offerings were put and watched the crowd putting their money into it.

One of his disciples said to him, “Look, Teacher! What massive stones! What magnificent buildings!”

“Do you see all these great buildings?” replied Jesus. “Not one stone here will be left on another; every one will be thrown down.”

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