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Midrash Tanchuma Buber, Sh'lach

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עמלק יושב (שם שם כט). מה ראו לפתוח בעמלק, משל למה הדבר דומה, לתינוק שסרח ולקה ברצועה, כשמבקשין להפחידו מזיכירין לו הרצועה, כך היה עמלק רצועה רעה לישראל, ומה ראה לישב לו עד הדרך, שכך ציוהו עשו זקנו לקדמו לדרך, ועקר ממקומו וישב לו בדרך, (וירד העמלקי והכנעני היושב בהר ההוא) [והחתי והיבוסי והאמורי יושב בהר] והכנעני יושב על הים ועל יד הירדן (שם), אלו הגבורים יושבים על הדרך, לפיכך נתכוונו המרגלים לשבר לבן של ישראל, שנאמר ויניאו את לב בני ישראל (שם לב ט).

Midrash Tanhuma, S. Buber Recension; trans. by John T. Townsend, 1989.

(Numb. 13:29:) AMALEK DWELLS IN THE LAND OF THE NEGEB. What reason did they see for opening with Amalek?⁴²., Numb. 4:9, cont.; Numb. R. 16:18. A parable: To what is the matter comparable? To a child who misbehaves and is beaten with a strap. When they wanted to intimidate him, they reminded him of the strap. Similarly Amalek had been an evil strap for Israel. What reason did he see to post himself {up to} in the way of Israel? He did so because his ancestor, Esau, had so commanded him in order to forestall them in their way. So he uprooted himself from his place and posted himself on the road. {(Numb. 14:45:) AND THERE WENT DOWN THE AMALEKITE, WHILE THE CANAANITE, WHO DWELT IN THAT MOUNTAIN.}⁴³ [(Numb. 13:29, cont.:) WHILE THE HITTITE, THE JEBUSITE, AND THE AMORITE DWELL IN THE MOUNTAINS,] AND THE CANAANITE DWELLS BY THE SEA AND ALONG THE JORDAN. These are the mighty ones dwelling on the way. Therefore the spies intended to break the heart of Israel, as stated (in Numb. 32:9): THEY TURNED AWAY THE HEART OF THE CHILDREN OF ISRAEL.

footnotes: ⁴² Tanh ⁴³ On this reading, Amalek used to dwell in the mountains, but came down to block Israel’s passage.