Why does it say "Harei va'Gilbo'a"? It is not Samuch!
Radak: It is as if it says Harim. We find [that the Samuch form is used even when it is not Samuch, e.g.] "Ovrei b'Emek ha'Bacha" (Tehilim 84:7), "ha'Shechuni va'Ohalim" (Shoftim 8:11).
What is the meaning of "u'Sdei Serumos"?
Rashi citing Targum Yonasan: There should not be enough grain in you [mountains] from which to separate Chalah 1 .
Radak: It is a field proper to separate Terumah from it. "Al" written about rain applies also to this; even if grain sprouts there, it should not be harvested, and Terumah will not be separated from it.
Malbim: They are choice fields on Rom (high) mountains, of Rom (high) quality.
I.e. the volume of 43.2 eggs of flour. Chalah is called Terumah (Bamidbar 15:20). (PF)
Why did he say "Nig'al Magen Giborim"?
Rashi: They had leather shields. When they went to war, they anointed them with oil, so weapons that struck them would slip off - "Kumu ha'Sarim Mishchu Magen" (Yeshayah 21:5). Here, the oil did not stick to it; it is as if it was not anointed. Hag'alah 1 is emitting what was put into it, e.g. "Shoro Iber v'Lo Yag'il" (Iyov 21:10; the ox' semen will not leave the womb without impregnating the cow).
Radak: [The mighty ones' shields] were despised 2 and cast off.
Malbim: "Magen" is a metaphor for the merit of Sha'ul and his sons. Their merit was like a shield for his nation.
Rashi (Iyov 21:10): This word is used also for Kashering in boiling water (to purge absorbed tastes).
This is like "v'Lo Sig'al Nafshi Eschem" (Vayikra 26:11). (PF)
Why does it say "Bli Mashi'ach ba'Shamen"?
Refer to 1:21:3:1.
Radak: It is as if Sha'ul was not anointed to be king.
Malbim: Their shield was not a leather shield anointed with oil, rather, of merits and good deeds. It was despised; his merit did not help, for the influence from above was removed.