Did Melech Ashur have a particular land in mind?
Rashi: He would exile them to Africa 1 .
Rashi (Yeshayah 36:17): No. After I find a land like yours, I will exile you to there.
Malbim: Yes. Refer to 18:32:3:2.
One opinion in Sanhedrin 94a says that this is where he exiled the 10 tribes. What is the source that he intended to exile Yehudah to the same place? Perhaps "a land like your land" means that there are Jews there. However, Rashi did not explain so! (PF)
Why did he promise them a land like their land?
Rashi (from Sanhedrin 94a): He was wise. Had he promised them a better land, they would know that he lies.
Rashi (Yeshayah 36:17) citing R. Shimon (Sifri Ekev 37)): Was he a fool, who did not know how to entice 1 ?! Rather, he could not find anything derogatory about Eretz Yisrael.
Sanhedrin 94a: He was a fool! Surely, people will not agree to move unless they think that the new land will be better 2 !
Emek ha'Netziv on the Sifri explains so.
Why is this foolish? People could agree to avoid dire starvation due to the siege. He says, do not refuse amidst concern lest your new land be worse than your current land! (PF) Also, if you resist me, I will exile you to a desolate land (Malbim Yeshayah 36:17)!
Why did he say both "a land of grain and wine" and "a land of bread and vineyards"?
Radak: Do not think that the grain and wine come from other cities. The land itself produces them.
Malbim (Yeshayah 36:17): Do not say that the new land is desolate, and before you can plow, plant and reap, you will starve. The grain and grapes are standing, and bread is prepared. I exiled its inhabitants when their vineyards were planted and their grain was grown.
Why will he exile them?
Radak: All nations that he conquered, he exiled them and put others in place of them ("v'Asir Gevulos Amim" - Yeshayah 10:13). This was so all would be conquered under him. Also Yosef did so to the Egyptians - "v'Es ha'Am He'evir Oso le'Arim" (Bereishis 47:21).
