Judgment Is To Come On That Generation Who Will Slay Jesus and His Followers In The Form Of The Destruction Of Jerusalem (23:37-39).
Jesus finishes with a lament over Jerusalem. It is not just the Scribes and Pharisees who have rejected Him, it is Jerusalem. They had been singled out because of their claim to religious significance, but in the end it was the whole of Jerusalem which had turned its back on Him. Time and again He had made His plea to them (note how His words assume a number of visits as portrayed in John's Gospel) but they had refused Him. Now only desolation could await them in the very house of God which would be left barren, for God was again departing from them as He had before (see Ezekiel 10:18-19; Ezekiel 11:22-23). But nevertheless He would return again, but only to those who welcomed Him in the Name of the Lord (as the pilgrims had welcomed Him into Jerusalem - Matthew 21:9). The idea is twofold. He would return in power after His resurrection through His disciples to all who would receive Him (Matthew 28:19-20; Acts 1-11), and He would return for His own at the last day (Matthew 24:31).
Analysis.
a “O Jerusalem, Jerusalem, which kills the prophets, and stones those who are sent to her! How often would I have gathered your children together, even as a hen gathers her chickens under her wings, and you would not!” (Matthew 23:37).
b “Behold, your house is left to you desolate” (Matthew 23:38).
a “For I say to you, You shall not see me henceforth, until you shall say, ‘Blessed is He who comes in the name of the Lord' ” (Matthew 23:39).
Note how in ‘a' He would have gathered them under His protection, and in the parallel they will one day say, ‘Blessed is He who comes in the name of the Lord'. Central in ‘b' is the certainty of the desolation of the Temple.