Commentary for Zechariah 14:10

The whole earth shall be changed The whole earth shall be changed to be like a plain. The mountains will be lowered, and the whole world will be a plain; and Jerusalem will be a mountain, so that it should appear higher than everything [else in the world].

from the hill of Rimmon We learned in Tosefta of Sotah (11:14): South of Jerusalem is a plain, and the hill of Rimmon is rocks and clods. Rather, so is [the] interpretation [of this phrase]: From the hill of Rimmon, which is a mountainous place from there [the mountains of the world] will begin to be changed, to [be] a plain; and they will be like the south of Jerusalem, which is a plain.

but it will be elevated high Since its entire environs are a plain, it will appear high.

and remain in its old place in its place

until the corner gate, and from the tower of Hananel which will also be in its place; and from there shall extend the length of the city until the king’s wine-cellars Jonathan renders: the pits off the king, fosec in Old French. [This is] like [a word in] Baba Kamma 50b, “trenches and caves.” And so, all wine cellars in Scripture are expressions of trenches, referring to the pit that is before the wine press, into which the wine flows. And the Midrash Aggadah (Pesikta d’Rav Kahana p. 143a; Song Rabbah 7:4, cf. Mattenoth Kehunnah, Radal) [identifies] the pits of the king with the ocean: that Jerusalem will reach the end of the whole world, the pits dug out by the supreme King of kings.