Notice that Jesus speaks of Jerusalem as if it was a person. You can almost feel the heartache in His words, the heartache wasn’t about Himself, it wasn’t about them rejecting Him, the heartache was all about the people, Luke 19:41.
Jesus looks to the future of Jerusalem and sees its destruction which was coming at the hands of the Romans in A.D. 70, Matthew 24:1-35 / Mark 13:1-31. We can almost hear the pain and frustration in Jesus’ words as He emphasises on Jerusalem, the city of David and the city of peace, Luke 13:34 / Matthew 23:37 / Luke 19:41-42.
They had killed God’s prophets and stoned them too, Luke 13:34 / Matthew 23:37 / Matthew 5:12 / Hebrews 11:32-40. God had longed to gather His children as a hen gathers her chicks, Luke 13:34 / Matthew 23:37. What a beautiful picture of love and protection this is, Deuteronomy 32:11 / Psalms 17:8 / Psalms 36:7 / Psalms 91:4 / Jeremiah 48:40. Sadly they were unwilling, Matthew 23:37.
Morgan, in his commentary, says the following.
‘Here, indeed, if ever, we have thoughts that breathe and burn. One can almost feel the withering force of his strong and mighty indignation, indignation directed, not against the people, but against their false guides. And yet behind it, all is his heart, and the woes merge into a wail of agony, the cry of a mother over her lost child.’
Because of their unwillingness to accept Jesus, Jesus says, ‘your house is left desolate’, Luke 13:35 / Matthew 23:38. Notice He uses the word ‘your’, it had become their house, not Gods, Luke 13:35 / Matthew 23:38 / Matthew 21:13. In other words, God’s house, the temple, had become desolate, that is, a symbol of everything opposite to God, 1 Kings 9:7-8 / Jeremiah 12:7 / Jeremiah 22:5.
Jesus tells them they will not see Him again, until they say blessed is he who comes in the name of the Lord, Luke 13:35 / Matthew 23:39 / Psalm 118:26 / Romans 11:26. These are the words which had greeted Jesus’ triumphal entry a few days before, Matthew 21:9. Is Jesus speaking about the day of judgment or the time when the Jews will be converted? Commentators are all over the place with this, so I guess it could be both.
Expositor’s Greek Testament, says the following.
‘He will not trouble them any more till their mood change and they be ready to receive Him with a Messianic salutation.’
Barnes, in his commentary, says the following.
‘This has not been yet accomplished, but the days will come when the Jews, long cast out and rejected, will hail Jesus as the Messiah, and receive him whom their fathers killed as the merciful Saviour, Romans 11:25-32.’
The Pulpit Commentary, says the following.
‘The clause, ‘till ye shall say,’ does not shut the door of hope forever, it looks forward to a happier prospect. The time intended is that when Israel shall repent of its rejection of the Messiah, and in bitter contrition look on him whom it pierced, owning and receiving Jesus with glad ‘Hosannahs!’ Then shall they behold him coming in power and glory and shall regain their old position as beloved of God, Hosea 3:4-5 / Zechariah 12:10. Then ‘all Israel shall be saved’, Romans 11:26. Thus this terrible chapter, so dark and menacing, closes with a glow of hope and a promise, indefinite but certain, of final restoration.’