במדבר כ״א:א׳-ג׳

וישמע הכנעני. שָׁמַע שֶׁמֵּת אַהֲרֹן וְנִסְתַּלְּקוּ עַנְנֵי כָבוֹד כו', כִּדְאִיתָא בְּרֹאשׁ הַשָּׁנָה (דף ג'), וַעֲמָלֵק מֵעוֹלָם רְצוּעַת מַרְדּוּת לְיִשְׂרָאֵל, מְזֻמָּן בְּכָל עֵת לְפֻרְעָנוּת:

The Canaanite heard. He heard that Aharon died, and the clouds of glory departed, etc. as stated in Rosh Hashanah. Amelek was always a whip for disciplining Israel, prepared, at all times, to mete out punishment.

ישב הנגב. זֶה עֲמָלֵק, שֶׁנֶּאֱמַר "עֲמָלֵק יוֹשֵׁב בְּאֶרֶץ הַנֶּגֶב" (במדבר י"ג), וְשִׁנָּה אֶת לְשׁוֹנוֹ לְדַבֵּר בִּלְשׁוֹן כְּנַעַן, כְּדֵי שֶׁיִּהְיוּ יִשְׂרָאֵל מִתְפַּלְּלִים לְהַקָּבָּ"ה לָתֵת כְּנַעֲנִים בְּיָדָם, וְהֵם אֵינָן כְּנַעֲנִים, רָאוּ יִשְׂרָאֵל לְבוּשֵׁיהֶם כִּלְבוּשֵׁי עֲמָלֵקִים וּלְשׁוֹנָם לְשׁוֹן כְּנַעַן, אָמְרוּ נִתְפַּלֵּל סְתָם, שֶׁנֶּאֱמַר "אִם נָתֹן תִּתֵּן אֶת הָעָם הַזֶּה בְּיָדִי" (עי' ילקוט שמעוני תשס"ד):

Who lived in the south. This was Amalek, as it is said, “Amelek dwells in the southern part of the land.” They changed their language, and spoke in the Canaanite tongue, so that the Israelites would pray to the Holy One, Blessed is He, to deliver the Canaanites into their hands —but they were not Canaanites. The Israelites saw that they were dressed in Amalekite clothing, but spoke the Canaanite tongue. They said, “let us pray in a general way,” as it is said, “if you will deliver this people into my hand.”

דרך האתרים. דֶּרֶךְ הַנֶּגֶב, שֶׁהָלְכוּ בּוֹ מְרַגְּלִים, שֶׁנֶּאֱמַר "וַיַּעֲלוּ בַנֶּגֶב" (במדבר י"ג); דָּבָר אַחֵר: דֶּרֶךְ הָאֲתָרִים, דֶּרֶךְ הַתַּיָּר הַגָּדוֹל הַנּוֹסֵעַ לִפְנֵיהֶם, שֶׁנֶּאֱמַר (שם י') "דֶּרֶךְ שְׁלֹשֶׁת יָמִים לָתוּר לָהֶם מְנוּחָה" (תנחומא):

By the route of the spies. The negev route traveled by the spies, as it is said, “they went up to the negev.” Another interpretation of דֶּרֶךְ הָאֲתָרִים ; the route of the great pathfinder which traveled before them, as it is said, “[the Ark of the covenant of God traveled before them] three days’ journey, to seek out a resting place for them.”

וישב ממנו שבי. אֵינָהּ אֶלָּא שִׁפְחָה אַחַת (ילקוט שמעוני שם):

He took from them a captive. It was only one maidservant.

והחרמתי. אַקְדִּישׁ שְׁלָלָם לְגָבוֹהַּ:

I shall consecrate. I shall consecrate the spoils to heaven.

ויחרם אתהם. בַּהֲרִיגָה:

And he destroyed them. By execution.

ואת עריהם. חֶרְמֵי גָבוֹהַּ:

And [consecrated] their cities. He consecrated them to heaven.