What is "u'Matzisa"?
Rashi: It is an expression of sucking.
Radak: You will drink it until the last drop.
Malbim: The first time it says "Shasis". The second time it says "u'Matzisa" ? even what is in the bottom of the cup. The third time "Es Charaseha Tegaremi" ? there will not be liquid in the bottom of the cup, only what is absorbed in the earthenware. The Nimshal is, the entire nation was eradicated. Only Yerushalayim, the Kli that still has liquid, you will break the city into pieces in order to suck more bitter liquid. I.e. the city will be burned and destroyed.
Why does it discuss shards of earthenware?
Rashi: It compares the cup of punishments for Yisrael to an earthenware Kli; once it breaks, it cannot be fixed. So once their salvation will come and the cup will be broken, He will not make them drink again. When the Navi discusses giving Nochrim to drink, it calls [the cup] gold ? "Kos Zahav Bavel b'Yad Hashem Meshakeres Kol ha'Aretz" (Yirmeyah 51:7).
Radak, Malbim: Wine is absorbed in the earthenware. It says Charaseha (plural), for it breaks into many pieces.
What is the meaning of "Tegaremi"?
Rashi: This is like "v'Atzmoseihem Yegarem" (Bamidbar 24:8), "Lo Garmu la'Boker" (Tzefanyah 3:3) - gnawing. His teeth scrape around the bone or earthenware to remove meat stuck to it.
Rashi citing Menachem: It is an expression of breaking 1 . And so he explained "v'Atzmoseihem Yegarem", "Lo Garmu la'Boker."
Radak, Malbim: After sucking the last drop, you will break the cup with your teeth, to suck the shards.
What is the meaning of "v'Shadayich Tenateki"?
Radak: They will be uprooted via drinking the poisonous cup. This is a Mashal ? the afflictions will be so sweet upon them, until they are utterly finished. Uprooting the Shadayim is a Mashal for Bitul of Toros in Galus. The Shadayim are a Mashal for written and oral Torah. In Galus Bavel they forgot Torah and nullified it. We find that they married Nochriyos, desecrated Shabbos and other matters that were not written, and even forgot Leshon [ha'Kodesh]!
Radak citing Targum Yonasan 1 : You will detach your flesh.
Malbim: With the broken shards you will uproot Shadayich amidst great pain. This is an awesome metaphor! Yerushalayim was like a mother to its children, the cities of Yehudah. It influences milk, and physical and spiritual food for everyone. The mother will uproot her breasts and cease to nurse her children ? the authority, "Kach Es ha'Leviyim" (Bamidbar 8:6) Avodah and Nevu'ah will all cease. All went from Yerushalayim to her villages.
Some texts of Radak say 'you will detach with your hair.' (PF)
