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Zechariah 12:2

Adam Clarke
Bible Commentary

Jerusalem a cup of trembling - The Babylonians, who captivated and ruined the Jews, shall in their turn be ruined.

I incline to think that what is spoken in this chapter about the Jews and Jerusalem, belongs to the "glory of the latter times."

Shall be in the siege - This may refer to some war against the Church of Christ, such as that mentioned Revelation 20:9.

Albert Barnes
Notes on the Whole Bible

I will make Jerusalem a cup of trembling - For encouragement, He promises the victory, and at first mentions the attack incidentally. Jerusalem is as a cup or basin, which its enemies take into their hands; a stone, which they put forth their strength to lift; but they themselves reel with the draught of God‘s judgments which they would give to others, they are torn by the stone which they would lift to fling. The image of the “cup” is mostly of God‘s displeasure, which is given to His own people, and then, His judgment of chastisement being exceeded, given in turn to those who had been the instruments of giving it. Thus, Isaiah speaks of “the cup of trembling.” Thou, “Jerusalem, hast drunk the dregs of the cup of trembling, hast wrung them out. Therefore hear thou this, thou afflicted and drunken but not with wine. Thus saith thy Lord, the Lord, and thy God that pleadeth the cause of His people, Behold, I have taken out of thine hand the cup of trembling, the dregs of the cup of My fury; thou shalt no more drink it again: but I will put it into the hand of them that afflict thee” Isaiah 51:17, Isaiah 51:21-23. Jeremiah speaks of “the cup of God‘s anger,” as given by God first to Jerusalem, then to all whom Nebuchadnezzar should subdue, then to Babylon itself Jeremiah 25:15-26; and as “passing through” to Edom also Lamentations 4:21; Jeremiah 49:12; Ezekiel, of “Aholibah” Ezekiel 23:31-33 (Jerusalem) “drinking the cup of Samaria.” In Jeremiah alone, Babylon is herself the cup. “Babylon” is “a golden cup in the Lord‘s hand, that made all the nations drunken; the nations have drunken of the wine; therefore the nations are mad” Jeremiah 51:7. Now Jerusalem is to be, not an ordinary cup, but a large “basin” or vessel, from which all nations may drink what will make them reel.

“And also upon Judah will it be in the siege against Jerusalem, that is, the burden of the word of the Lord which was on Israel” should be “upon Judah,” that is, upon all, great and small.

Matthew Henry
Concise Bible Commentary
Here is a Divine prediction, which will be a heavy burden to all the enemies of the church. But it is for Israel; for their comfort and benefit. It is promised that God will make foolish the counsels, and weaken the courage of the enemies of the church. The exact meaning is not clear; but God often begins by calling the poor and despised; and in that day even the feeblest will resemble David, and be as eminent in courage and every thing good. Desirable indeed is it that the examples and labours of Christians should render them as fire among wood, as a torch in a sheaf, to kindle the flame of Divine love, to spread religion on the right hand and on the left.