Zechariah 12:2

“Behold, I will make Jerusalem a cup of trembling unto all the people round about, etc.] The Targum renders it, “a vessel full of inebriating liquor;” which intoxicates and makes giddy, and causes to tremble, stagger, and fall like a drunken man. The phrase denotes the punishment inflicted by the Lord upon the enemies of his church and people; (see <235122>Isaiah 51:22,23): when they shall be in the siege both against Judah [and] against Jerusalem; not by Antiochus Epiphanes; nor by Titus Vespasian; nor by Gog and Magog, as Kimchi; but by the antichristian powers, especially the Mahometan nations, the Turks, which shall come against Jerusalem, when the Jews are returned thither, and resettled…”

“cup of trembling--a cup causing those who drink it to reel (from a Hebrew root "to reel"). Jerusalem, who drank the "cup of trembling" herself, shall be so to her foes (Isa 51:17, Isa 51:22; Jer 13:13). CALVIN with the Septuagint translates, "threshold of destruction," on which they shall stumble and be crushed when they attempt to cross it. English Version is better. both against Judah--The Hebrew order of words is literally, "And also against Judah shall he (the foe) be in the siege against Jerusalem"; implying virtually that Judah, as it shares the invasion along with Jerusalem, so it shall, like the metropolis, prove a cup of trembling to the invaders. MAURER with JEROME translates,…”

“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…”

“Jerusalem - That weak, unwalled city, and much more the church which is the antitype of Jerusalem. In the siege - Now when all this is in readiness, and no visible means of escape, then will God make them drink the wine of astonishment. Zechariah 12:3”

“12:2 intoxicating drink (literally bowl of reeling or cup of staggering): The cup of alcoholic drink is a metaphor for God’s judgment (Isa 51:17; Jer 25:15; Hab 2:16; Matt 26:39, 42; Rev 14:10; 16:1). Jerusalem would be instrumental in God’s judgment on the nearby nations.”

“a cup: Psa 75:8; Isa 51:17, Isa 51:22, Isa 51:23; Jer 25:15, Jer 25:17, Jer 49:12, Jer 51:7; Hab 2:16; Rev 14:10, Rev 16:19, Rev 18:6 trembling: or, slumber, Jer 51:57, or, poison, Jer 8:14 when they: etc. or, and also against Judah shall he be, which shall be in siege against Jerusalem, Zac 14:14 Zechariah 12:3”

“"Behold, I make Jerusalem a reeling-basin for all the nations round about, and upon Judah also will it be at the siege against Jerusalem. Zac 12:3. And it will come to pass on that day, I will make Jerusalem a burden-stone to all nations: all who lift it up will tear rents for themselves; and all the nations of the earth will gather together against it. Zac 12:4. In that day, is the saying of Jehovah, will I smite every horse with shyness, and its rider with madness, and over the house of Judah will I open my eyes, and every horse of the nations will I smite with blindness." These verses allude to an attack on the part of the nations upon Jerusalem and Judah, which will result in injury and…”