In Matthew 23, Jesus gives a fiery speech to the Scribes and Pharisees. Seven times the Lord pronounces woe upon the leaders of the people (Matt.23:13,15,16,23,25,27 and 29). Jesus calls them, among other things, a brood of vipers (:33) and whitewashed graves (:27), beautiful on the outside, but dead on the inside.
judgement
Just as Stephen would later do in his speech to the Sanhedrin (Acts 7:51-52), Jesus says that they have always persecuted and killed the prophets sent by God and other sent ones. At the time Jesus gave this speech, He Himself would be crucified within a few days. The Lord announces judgment on the people.
Matthew 23
36 Amen! I say to you, All these things will come upon this generation.
this generation
This generation, is ambiguous, because this generation speaks of the Jewish people, but also of the period of forty years (> a generation, Heb.3:9-10) that would pass until the city of Jerusalem and the temple would be destroyed by the Romans (70 AD). The judgment that the Lord pronounced would come upon this people and it would be carried out by the Romans in 70 AD, forty years later.
37 Jerusalem, Jerusalem, who kills the prophets and stones those who come to her, how often will I gather your children together, as a hen gathers her chicks under her wings; and you don’t want to.
protection
The analogy of a hen gathering her chicks speaks of care and protection. It is a comparison that we find several times in the Hebrew Bible (Ps.17:8; 36:7; 57:1; 91:4). God stretches out His hand to His people, but they are unwilling and turn away from Him.
38 Behold, your house is left desolate to you.
the house
The house here in a narrow sense concerns the temple, somewhat broader: Jerusalem, and even broader: the entire nation of Israel. The Lord would leave the people, in the sense of letting go. He withdraws His hands from the people and will hide His face from them (Deut.31:17,18; 32;20).
The house of Israel would be left desolate. Elsewhere this word desolate is translated as desert or wilderness (Matt. 3:1; Heb. 3:8) and also has to do with lonely (Gal. 4:27).
Here too the Lord refers to the Hebrew scriptures (Ps.69:26).
Israel was judged because of their unbelief. Jerusalem and the temple were destroyed and reduced to ashes by the Romans in 70 AD. Many Jews died and the survivors were sold as slaves. The land became a desolation and Israel disappeared into the dispersion (diaspora).