Chrysostom on Matthew 23:37

3. Then He directs His speech unto the city, in this way too being minded to correct His hearers, and saith, “O Jerusalem, Jerusalem!” What meaneth the repetition? this is the manner of one pitying her, and bemoaning her, and greatly loving her. For, like as unto a woman beloved, herself indeed ever loved, but who had despised Him that loved her, and therefore on the point of being punished, He pleads, being now about to inflict the punishment. Which He doth in the prophets also, using these words, “I said, Turn thou unto me, and she returned not.”

Then having called her, He tells also her blood-stained deeds, “Thou that killest the prophets, and stonest them that are sent unto thee, how often would I have gathered thy children together, and ye would not,” in this way also pleading for His own dealings; not even with these things hast thou turned me aside, nor withdrawn me from my great affection toward thee, but it was my desire even so, not once or twice, but often to draw thee unto me. “For how often would I have gathered your children together, even as a hen gathereth her chickens, and ye would not." And this He saith, to show that they were ever scattering themselves by their sins. And His affection He indicates by the similitude; for indeed the creature is warm in its love towards its brood. And everywhere in the prophets is this same image of the wings, and in the song of Moses and in the Psalms, indicating His great protection and care.

“But ye would not,” He saith. “Behold your house is left desolate,” stripped of the succor which cometh from me. Surely it was the same, who also was before protecting them, and holding them together, and preserving them; surely it was He who was ever chastening them. And He appoints a punishment, which they had ever dreaded exceedingly; for it declared the entire overthrow of their polity. “For I say unto you, Ye shall not see me henceforth, till ye shall say, Blessed is He that cometh in the name of the Lord.” And this is the language of one that loves earnestly, earnestly drawing them unto Him by the things to come, not merely warning them by the past; for of the future day of His second coming doth He here speak.

What then? Did they not see Him from that time? But it is not that hour which He meaneth in saying, Henceforth, but the time up to His crucifixion. For since they were forever accusing Him of this, that He was a kind of rival God, and a foe to God, He moves them to love Him by this, namely, by showing Himself to be of one accord with His Father; and He indicates Himself to be the same that was in the prophets. Wherefore also He uses the same words as did the prophets.

Chryosostom, "Homilies on the Gospel of Saint Matthew," NPNF, 1st Series, ed. Philip Schaff (Peabody, MA: Hendrickson, 2004), 10:447-448.