|Sack of Jerusalem, from the Arch of Titus in Rome|
If someone tells you that both Caesarea (the Roman colonial capital of Judea) and Jerusalem are in ruins or that both are inhabited, do not believe him. But if he says that Caesarea is in ruins and Jerusalem is inhabited or that Caesarea is inhabited and Jerusalem is in ruins, believe him, as it says, 'I shall be filled with her that is laid waste' - If one is full, the other is in ruins, if one is in ruins, the other is full (Megillah 6a)
Rav Nachman said: Initially, when they brought wine libations from Judah , their wine never became sour. but now it is the wine of the Edomites that does not become sour, as it says: 'I shall be filled with her that is laid waste' If one is full, the other is in ruins, if one is in ruins, the other is full (Pesachim 42b)
Rashi: 'I shall be filled with her that is laid waste' this verse (Ezekiel 26:2) begins with 'Tzor said to Jerusalem...I will become full from her destruction' and Tzor is from Edom.
According to Rabbi Avraham Yehoshua Greenbaum, on the pshat level, the Tzor from the verse in Ezekiel that capitalizes on Jerusalem's destruction refers to the Lebanese city of Tyre, the center of maritime trade in the Mediterranean (note the passage of Iranian warships this week through the present-day centers of Mediterranean trade).
However, according to Rabbi Eliezer, "every place in the Bible where tzor is spelled chaser (i.e. without the vav, i.e. tzr instead of tzr), it refers to Edom." (Tanchuma Va-Era ch. 13) Without the vav, Tzar means oppressor, or Rome, which became present-day Western civilization, while the root tzor with a vav means to create, as in the center of trade.
On the pshat level, "Aha! I shall be filled with her that is laid waste" refers to the destruction of Tyre in the hands of Nebuchadnezzar. However, according to the rabbinic interpretation of the verse in Pesachim and Megillah, the verse refers to Rome's glee at the destruction of Jerusalem and the downfall of Israel. Hashem does not forget; because Rome used Israel's destruction for its own advantage, history will proceed according to the dialectic tension between Rome and Jerusalem.
"אמלאה החרבה" (יחזקאל כו, ב) אם מלאה זו חרבה זו ואם מלאה זו חרבה זו (פסחים מ"ב ע"ב)
רש"י: אמלאה החרבה - רישא דקרא יען אמרה צור לירושלים האח וגו' אתמלא מן חורבנה של ירושלים וצור מאדום היא:
אם יאמר לך אדם חרבו שתיהן אל תאמן ישבו שתיהן אל תאמן חרבה קסרי וישבה ירושלים חרבה ירושלים וישבה קסרי תאמן שנאמר (יחזקאל כו, ב) אמלאה החרבה אם מליאה זו חרבה זו אם מליאה זו חרבה זו (מגילה ו ע"א)
בן אדם יען אשר אמרה צר על ירושלים: האח! נשברה דלתות העמים, נסבה אלי אמלאה החרבה (יחזקאל כו, ב)
והמבין יבין She who is wise will understand