John Gill's Exposition of the Whole Bible
Isaiah 37:22
This is the word which the Lord hath spoken concerning him,.... The sentence he has pronounced upon him, the punishment he has determined to inflict on him, in answer to Hezekiah's prayer against him:
the virgin, the daughter of Zion; hath despised thee; and laughed thee to scorn; that, is the inhabitants of Zion, particularly of the fort of Zion, called a "virgin", because it had never been forced, or taken and to show that it was a vain thing in Sennacherib to attempt it, as well as it would have been an injurious one, could he have accomplished it; since God, the Father of this virgin, would carefully keep her from such a rape; and he who was her husband to whom she was espoused as a chaste virgin, would defend and protect her; and the whole is designed to show the impotent malice of the king of Assyria; otherwise, at the time when these words were spoken, the daughter of Zion was in a fearful and trembling condition, and not in a laughing frame; but this declares what she might do now, and would do hereafter, for anything that he could do against her. The Targum paraphrases it,
"the kingdom of the congregation of Zion;''
the whole nation. Some restrain this to the inhabitants of the upper part of the city of Jerusalem, as what follows to those of the lower part:
the daughter of Jerusalem hath shaken her head at thee; or "after thee o"; by way of scorn and derision; that is when he fled; which shows, that though these things are spoken as if they were past, after the manner of the prophets, yet were to come, and would be when Sennacherib fled, upon the destruction of his army. Of this phrase, as expressive of scorn, see Psalms 22:7. The Targum is, "the people that dwell in Jerusalem", c.
o אחריך "post te", V. L. Pagninus, Montanus Junius Tremellius, Piscator.