21:1כ״א:א׳
1 א

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

וישמע הכנעני AND THE CANAANITE HEARD — He heard that Aaron had died and that the clouds of glory had disappeared and he believed that now he was at liberty to wage war against Israel, as it is related in Rosh Hashana 3a; Amalek was from olden times a whip for chastising Israel — always held in readiness to be God's agent for Israels punishment (Midrash Tanchuma, Chukat 18).

2 ב

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):

ישב הנגב THE INHABITANT OF THE SOUTH COUNTRY — This was Amalek,as it is said, (Numbers 13:29), “Amalek was the inhabitant of the south country”. But he purposely changed his speech, talking in the “Canaanite” tongue, so that Israel might thereby be misled and would pray to the Holy One, blessed be He, that he should give the Canaanites into their power, whilst really they were not Canaanites, and their prayer would be ineffectual against the Amalakites. But Israel perceived that their clothing was as the clothing of Amalakites whilst their language was the language of Canaan; they thereupon said, “Let us pray against our enemies in general terms (without mention of any name), as it is stated (v. 2) that they said, “if Thou wilt indeed give this people into my hand”.

3 ג

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):

דרך האתרים BY WAY OF ATHARIM — by way of the south country by which the spies (תרים) had gone, as it is said, (Numbers 13:22) “and they went up by the south country”. Another explanation of דרך האתרים is: By the way of the Great Searcher (the Ark) which used to journey in front of them, as it is said, (Numbers 10:33) “[and the Ark of the Covenant of the Lord went before them] in the three days’ journey to search out (לתור) a resting-place for them” (Midrash Tanchuma, Chukat 14).

4 ד

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

וישב ממנו שבי (more lit.,) AND CAPTURED FROM THEM A CAPTIVE — it was only one maid servant (Yalkut Shimoni on Torah 764).