Matthew 23:37

O Jerusalem, Jerusalem, that killeth the prophets, and stoneth them that are sent unto her! how often would I have gathered the children together, even as a hen gathereth her chickens under her wings, and ye would not!

Morgan's comment on this chapter has this passage:

Here, indeed, if ever, we have thoughts that breathe and burn. One can almost feel the withering force of his strong and mighty indignation - indignation directed, not against the people, but against their false guides. And yet behind it all is his heart; and the woes merge into a wail of agony, the cry of a mother over her lost child.[12]

This lament over the doomed city occurred at a most appropriate time: upon the occasion of the Lord's sentencing her to destruction. One who has ever attended a courtroom in which the judge announced a death sentence and has observed the heart-breaking scenes that inevitably follow can appreciate the sorrow that overwhelmed the Saviour in that tragic hour when the glory and power of Jerusalem, the city of the great King, as Jesus himself called it, were consigned to the torch and the sword, the heel of the invader, the pestilence and the siege, the brutality of plunder, and the dashing of the heads of her infants against the stones! "Sin when it is finished bringeth forth death" (James 1:15, KJV). Sin for Jerusalem was finished by the rejection of Christ, and it brought forth death. A cry of pity and of sorrow went up from her Saviour, but not even that could spare Jerusalem.

Ye would not! Man's freedom of the will makes it possible for him to reject even his God; but when he does so, he cannot avoid the consequences.

The reference to a hen and chickens is one of the tenderest, commonest, and most appealing figures Jesus ever used. The common barnyard fowl was to be used again by our Lord in the incident of Peter's denial. The commonest and most ordinary things on the planet grew luminous at the touch of Jesus and sprang into glorious significance.

As for the particular time when the above lament was spoken, Matthew's including it at this juncture might not be chronological. F. W. Farrar placed it on the day of the Triumphal Entry and treated it as occurring as Christ approached the city along the southern route from Bethany on Palm Sunday.[13] We believe Farrar was following Luke's account which certainly places it on that day (Luke 19:41), but Luke also gives a second weeping over the city (Luke 13:34), and it is reasonable to suppose there may have been a third one, in which case Matthew's account might very well be a chronological record of it. Certainly, the sheer logic of Jesus' weeping upon the very occasion of sentencing the city to its doom lends support to such a consideration.

[12] G. Campbell Morgan, An Exposition of the Whole Bible (Westwood, New Jersey: Fleming H. Revell Company, 1959), p. 420.

[13] F. W. Farrar, The Life of Christ (New York: A. L. Burt Company), p. 378.