1)

Why did he say "you and your sons will be with me"?

1.

Rashi citing Brachos 12b: You will be in my place [in the world to come]. 1

2.

Radak: You will be dead, like me.

1

Radak: In the reward of going to war in order to die, and not fleeing, this will atone for the sin of Nov, and you will be in my place, of Tzadikim. Brachos 12b says that it was because he was ashamed of killing the Kohanim (refer to 28:15:3:1).

2)

Why will Yisrael be handed over to the Pelishtim?

1.

Malbim: They also were part of the sin [of not totally destroying Amalek]. They had mercy on the animals. They should have protested against Sha'ul, since they knew the Navi's command!

Sefer: Perek: Pasuk:

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