What is the meaning of "Heilili Sha'ar Za'aki Ir"?
Radak citing Targum Yonasan: Mourn over the gate and scream over the city, for the great breakage that comes to you.
Why does it say "Namog Peleshes Kulach"?
Radak: All of Peleshes will melt and be broken. It is masculine, due to the Am (nation); "Heilili" (feminine) is due to the Edah (congregation).
Malbim: Sancheriv conquered Pelishtim three years before he fell in Eretz Yehudah. When he came to Yehudah to seize it, he passed close to Eretz Pelishtim. They melted amidst fear lest he come against them again. They sent spies to see [his intent], and found out that he fell in Har Tziyon. Pelishtim are compared to wax that melts due to a fire. Here, the fire did not come, only the smoke; the fire was still far away. I.e. the enemy is destroying in the north.
What smoke comes from the north?
Rashi: Punishment harsh like smoke will come from the north. Chizkiyah struck Azah and its borders; they are in the southwest corner of Eretz Yisrael; Eretz Yisrael is north of it. Sifri (Ha'azinu 322) - if Yisrael wanted to flee to the south, the nations closed them off - "Al Sheloshah Pish'ei Azah" (Amos 1:6).
What is the meaning of "v'Ein Boded b'Mo'adav"?
Rashi citing Targum Yonasan: No one delays in his time. The troops that he designated to come against you, no one will be late and come Boded (alone). Rather, all will come together strongly.
Radak citing Targum Yonasan: In the times that Chizkiyah will set to go to fight Pelishtim, no Yisrael will be alone and not go with the army. All will go happily!
Malbim: [Sancheriv] does not send isolated soldiers. He sends camps from every side. Surely one of his camps will pass via our land, and destroy it a second time.
