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When the spies come back, all of them (aside from Yehoshua Bin Nun and Calev Ben Yefuneh) return with negative reports of the land. Among these reports is a reference to Amalek: “Amalek dwell in the south land.” Rashi brings the Midrash Tanchuma to explain their mentioning of Amalek: “Since they had already been ‘burned’ by Amalek, [i.e. previously having had a war with them] the spies mentioned it in order to strike fear in them.”

This Midrash is at first glance very troubling. Where do we see in the mentioning of Amalek that the spies had ulterior motives? Is it not logical that spies sent to scout out the land would mention that the nation’s sworn enemy is in the vicinity? Is this not a very pertinent piece of intelligence for the nation before entering the land in order to conquer it? The very fact that Klal Yisrael “got burned” and had past issues with Amalek makes it so much more important to mention this! It seems that the spies are simply fulfilling their mission to provide the necessary information to conquer the land.

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The impetus for the drasha in the medrash is specifically because the first nation the spies mentioned was amalek, and as the ikar sifsei chachamim explains why not mention the amori and chiti who live in the mountains first, must be they were trying to scare klal yisrael with the bad memory as the medrash continues with the mashal of the child who got hit etc.

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To add to your point, Amalek was not one of the nations that the Bnei Yisrael were told they must attack to conquer their land, unlike the Emori and Chiti. –  Eliyahu Jun 20 at 0:52

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