This passage is the prelude to the next two chapters in Matthew. It is a warning to the nation of Israel. Matthew 23:37-39 is the sorrow of Messiah (Yeshua) because He came to deliver but had been rejected. Matthew 24-25 speaks of the Tribulation. This Tribulation is for Israel in the Last Days. Those who live at that time will understand perfectly. Jesus is Prophet, Priest, and King. He prophesies the times of hardship for Israel, judgment, and the conditions needed for His return. These chapters refer to the Second Coming of Jesus, not the Rapture. Here is my translation and notes.
37 “O Jerusalem, Jerusalem who kills the prophets and stones those who are sent to yous. How often I wanted to gather yours children together even like a hen gathers her chicks under [her] wings, but youp determinately would not.
[Messiah came to deliver His people, but the nation and its leaders refused to believe. God wills for all to believe, but most refuse due to pride and love for sinful pleasures. See Psalm 10:4, John 3:19, and 2 Thessalonians 2:12].
38 “Look, yourp house is left to youp desolate.
[Israel was not a nation for many centuries. There was destruction not deliverance. Deliverance is coming. The situation at Armageddon will be so severe that the nation knows they will not exist anymore. They study the prophets and understand, with the help of the Holy Spirit, that the Jesus of the New Testament is the promised Messiah].
39 “For I say to youp, ‘Youp will not see me anymore, until youp say, ‘Blessed [is] he who comes in the name of the Lord.’” [Psalm 118:26]
[Dr Arnold Fruchtenbaum teaches (Video entitled “The Final Sign—Jesus is About to Come Back)” that the conditions for Israel for Messiah to come are found in 5 passages. Leviticus 26:40-42 states that God will fulfill His promises. One thing they do is confess their iniquity. Iniquity is singular, according to Dr Arnold Fruchtenbaum. The second is Jeremiah 3:11-18 which lists some Millennial kingdom blessings for Israel. Verse 14 one sin which must be confessed to have these blessings. The third passage is Zechariah 12:10. The blessings are listed in Zechariah 13-14. They must look unto the one they have pierced and plead for his return. They must acknowledge Jesus before He will return. Hosea 5:15 is the fourth passage. The prophet gives God message that the nation of Israel must confess their guilt and seek Him. This sin/iniquity that they must confess is the sin of accusing Messiah Yeshua of being demonized. Matthew 23:37-39 is the fifth passage. The nation must confess, “Blessed [is] he who comes in the name of the Lord.” They must confess their sin of accusing Him of be demonized and plead for Jesus to return. Compare Hosea 6:1-3 which is a continuation of Hosea 5:15, for the new chapter should start with Hosea 6:4. Verses 1-3 is the response of Israel from their leaders to seek Yeshua. The call comes from the leaders. The first 2 days they confess their sin, and the last day call for Him to return. These are the last 3 days of the Tribulation. Dr Fruchtenbaum believes Isaiah 53:1-9 is the words of the nation’s confession of sins. They realize that Jesus of the New Testament is the Messiah. The plea for return is Psalm 79:1-14 and Psalm 80. Note Psalm 80:17—the man at your right hand, the Son of Man. See Luke 22:69, Romans 8:34, and Hebrews 1:13].