יחזקאל, פרק כ״ג, פסוק ל״א

A tragic repetition of past sins inevitably leads to an identical and unavoidable fate. Jerusalem chose to follow the exact path of its sister, Samaria, failing entirely to learn from history. This chosen path represents a complete abandonment of God in favor of relying on the power of foreign nations and idol worship [אברבנאל]. The guilt of Jerusalem is especially severe because the city actually witnessed the punishment its sister suffered, yet refused to absorb the moral lesson [מלבי״ם].

Because of this deliberate choice, the divine response is to hand Jerusalem the very same bitter cup of disaster. Commentators widely agree that this cup serves as a metaphor for punishment and the anger of God, though they offer different descriptions of what it contains. Some describe it as a hot cup filled with intoxicating wine that completely confuses a person's mind [מצודת דוד], while others view it as a drink of pure bitterness and poison [ביאור שטיינזלץ]. Another unique approach suggests the cup represents the bitter waters given to an unfaithful wife, serving as a highly symbolic punishment that perfectly matches the city's betrayal [מלבי״ם]. Ultimately, the drink within is not a wine of joy, but a deadly poison that brings a drunkenness of sadness, leaving behind nothing but destruction and ruin in the land [אברבנאל].