“O Jerusalem, Jerusalem, the one who kills the prophets and stones those who are sent to her! How often I wanted to gather your children together, as a hen gathers her chicks under her wings, but you were not willing! 38 See! Your house is left to you desolate; 39 for I say to you, you shall see Me no more till you say, ‘Blessed is He who comes in the name of the Lord!’” — Matthew 23:37-39.
How often I wanted to gather your children together. — Not only had the city been warned again and again by the prophets, but the Lord had visited it at least six or seven times, and had for months taught in its streets. Nor did his concern end with the cross. His long suffering, patience and love are shown by his charge in the commission to the apostles: “that repentance and remission of sins should be preached in His name to all nations, beginning at Jerusalem” (Luke 24:47).
You were not willing. — “Were not” explains the cause of the rejection of the gospel. It is not because God in Christ is not ready: he “wanted to gather” them. It is not because men cannot come, but because they will not come. Christ wished the salvation of Jerusalem; his will was for them to be saved: he sought to influence their wills to make a choice of salvation, but they “were not willing”. So God is still “not willing that any should perish but that all should come to repentance” (2 Peter 3:9). As our Lord declared, “you are not willing to come to Me that you may have life” (John 5:40). While God wills the salvation of men, he does not destroy free agency by coercing the human will, but says: “Whosoever desires, let him come” (see Revelation 22:17).
“Your house is left to you desolate” – Because of their rejection of the Messiah and His departure from them. This appears to be an allusion to Jeremiah 22:5. It could refer to the destruction of Jerusalem in AD 70 or to other future events. God’s unique covenant with Israel has been altered by their unbelief! There is a New Covenant (cf. Jeremiah 31:31-34), which is not based on racial descent, but on faith and faithfulness in God and His Messiah.
“you shall see Me no more till you say” — This is a reference to Psalm 118:26-27, which was used in the Triumphal Entry (cf. Matthew 21:9). This is similar to the wonderful Messianic prediction of Zechariah 12:10 that the Jews will one day turn to the one whom they pierced (cf. Romans 9-11)! The context seems to point more to the judgment of national Israel and the extension of the promises to spiritual Israel, made up of Gentiles as well as Jews (v. 38; cf. 21:43).