This lamentation should help us realize that the judgment Jesus just announced in such strong language was not something that delighted Him. It broke His heart. This is also clear from His personalizing the people in Jerusalem in these verses. Jesus spoke of the city as many people, not as an impersonal thing. He also spoke here as Israel's Savior, not just a prophet but God Himself. These three verses are Jesus' last public words to Israel that the evangelists recorded.
"Jesus' lament over Jerusalem revealed that He made a legitimate offer of the kingdom to Israel and that it was His desired will that they would respond. As a result of their having rejected such a contingent offer, their house was destroyed. . . . The time from His rejection to His return is the mystery' phase of the kingdom, as described in Matthew 13. The final phase of that period is outlined in chapters 24-25."848
23:37 Jerusalem was the city of David and the city of peace. It was the city God had chosen to reveal Himself to Israel through the temple and as the capital of His kingdom on earth. However it (personified) had killed the prophets God had sent to His people with His messages. Stoning was the penalty for the worst crimes in Israel, including false prophecy. The people had used this form of execution on those who faithfully brought God's Word to them. Jesus' words recall His ancestor David's sorrow over the death of his son Absalom (2 Sam. 18:33; 19:4). The repetition of "Jerusalem"reveals the strong emotion that Jesus felt (cf. Luke 10:41; Acts 9:4).
Many times during His ministry Jesus had sought to gather and shelter Jerusalem, used here by synecdoche to represent the whole nation.849He wanted the people to take refuge in Him as chicks do under their mother hen physically and as God's people had done under God's care spiritually (cf. Deut. 32:11; Ps. 17:8; 36:7; 91:4; Jer. 48:40). In spite of God's loving initiatives Israel had willfully rejected Him repeatedly. Jesus' identification with God is very clear in this verse (cf. Ezek. 18:32). Jeremiah prefigured Jesus as he sadly anticipated Jerusalem's destruction by the Babylonians in the Book of Lamentations.
23:38 The house in view is probably the temple (cf. 1 Kings 9:7-8).850Jesus had formerly claimed it as His own house (5:35; 17:25-26; 21:12-16). Now He spoke of it as their house, the house of prayer that they had converted into a den of thieves (21:13). Jesus and God would leave the temple desolate by removing Jesus' presence from it. Instead of it becoming the focal point of worship during the messianic kingdom, it would be devoid of Immanuel, God with us, until He returns to it (1:23; cf. Jer. 12:7; 22:5). Instead of bringing promised rest and blessing to Israel, Messiah would leave her desolate.
23:39 Jesus quoted Psalm 118:26 (cf. 21:9). He was referring to His return to the temple in power and great glory when He returns at His second coming, not to some return to the temple before His ascension. The negative is very strong in the Greek text (ou me). When He returns, all will acknowledge Him instead of rejecting Him (cf. Zech. 12:10). Moreover He will come in judgment (cf. 24:30-31; Phil. 2:9-11; Rev. 1:7).
"It is extremely important for one to note that Christ's rejection of Israel is not an eternal one. The word until' (eos) of verse thirty-nine together with the following statement affirms the fact that Christ will come again to a repentant nation to establish the promised millennial kingdom."851
Having said His good-bye to the temple, Jesus left its courtyard where He had spent a busy Wednesday teaching (21:18-23:46).
"Surprisingly, Jesus' teaching occasions less conflict in Matthew's story than one would expect. The reason is that the religious leaders are the recipients of none of the great discourses of Jesus [chs. 5-7; 10; 13; 18; 24-25], and even Jesus' speech of woes is not delivered to the scribes and Pharisees but to the disciples and the crowds (chap. 23). It is in certain of the debates Jesus has with the religious leaders that his teaching generates conflict."852
