1)

What is the significance of the fact that the Amaleki and the Cana'ani dwelt in the valley?

1.

Rashi: It is a warning that, if they move forward, the Amalekim and the Cana'anim will kill them, since Hashem is not with them.

2)

How will we reconcile the current Pasuk "ve'ha'Amaleki ve'ha'Cana'ani Yoshev ba'Eimek with the Pasuk in 13:29, where the spies stated that Amalek dwelt in the south and the Cana'ani by the sea?

1.

The spies mentioned those whom they saw on their travels. 1 Perhaps they saw a minority on the border, and most of these nations lived elsewhere, in the interior.


1

Rashi explained in 13:21 that they traveled along the southern border, and then along the western border (the sea). (PF). Incidentally, Rashi did not explain how they returned from the northwest corner. Presumably, they traveled along the north and then along the east (Yarden); they said that they saw Cana'ani by the Yarden - 13:29 (PF).

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