אשר קרך בדרך. לְשׁוֹן מִקְרֶה; דָּבָר אַחֵר — לְשׁוֹן קֶרִי וְטֻמְאָה שֶׁהָיָה מְטַמְּאָן בְּמִשְׁכַּב זְכוּר; דָּ"אַ — לְשׁוֹן קֹר וְחֹם, צִנֶּנְךָ וְהִפְשִׁירְךָ מֵרְתִיחָתְךָ, שֶׁהָיוּ כָל הָאֻמּוֹת יְרֵאִים לְהִלָּחֵם בָּכֶם וּבָא זֶה וְהִתְחִיל וְהֶרְאָה מָקוֹם לַאֲחֵרִים; מָשָׁל לְאַמְבָּטִי רוֹתַחַת שֶׁאֵין כָּל בְּרִיָּה יְכוֹלָה לֵירֵד בְּתוֹכָהּ, בָּא בֶן בְּלִיַּעַל אֶחָד קָפַץ וְיָרַד לְתוֹכָהּ, אַעַ"פִּ שֶׁנִּכְוָה הֵקֵרָהּ אוֹתָהּ בִּפְנֵי אֲחֵרִים (תנחומא): אשר קרך בדרך HOW HE MET THEE BY THE WAY — The word קרך is connected in meaning with מקרה “a sudden happening”, i.e., he came against thee by surprise. Another explanation is: it is connected in meaning with the term קרי, nocturnal pollution and uncleanness, because he polluted them by pederasty. Yet another explanation is that it is connected in meaning with the expression קור in the phrase קור וחום “cold and heat” and it means: he made you cold and lukewarm after the boiling heat you had before. For all the nations were afraid to war against you and this one came and began to point out the way to others. A parable! It may be compared to a boiling hot bath into which no living creature could descend. A good-for-nothing came, and sprang down into it; although he scalded himself he made it appear cold to others (Midrash Tanchuma, Ki Teitzei 9).
ויזנב בך. מַכַּת זָנָב, חוֹתֵךְ מִילוֹת וְזוֹרֵק כְּלַפֵּי מַעְלָה (תנחומא): ויזנב בך means, smiting the membrum; he cut off the membra and threw them up provocatively towards Heaven (God) (Midrash Tanchuma, Ki Teitzei 10).
כל הנחשלים אחריך. חַסְרֵי כֹחַ מֵחֲמַת חֶטְאָם, שֶׁהָיָה הֶעָנָן פּוֹלְטָן (תנחומא): כל הנחשלים אחריך [AND HE SMOTE THE HINDMOST OF THEE] EVEN THOSE THAT WERE FEEBLE BEHIND THEE — i.e., those who were enfeebled because of their sins and whom the clouds had expelled from the protection they afforded (Midrash Tanchuma, Ki Teitzei 10).
ואתה עיף ויגע. עָיֵף בַּצָּמָא, דִּכְתִיב "וַיִּצְמָא שָׁם הָעָם לַמַּיִם" (שמות י"ז) וּכְתִיב אַחֲרָיו "וַיָּבֹא עֲמָלֵק": ואתה עיף ויגע AND THOU WAST FAINT AND WEARY — faint through thirst, for it is written, (Exodus 17:3) “And the people thirsted there for water” and it is written immediately afterwards (v. 8) “Then came Amalek”.
ויגע. בַּדֶּרֶךְ: ויגע AND WEARY — from the journey (Midrash Tanchuma, Ki Teitzei 10).
ולא ירא. עֲמָלֵק אלהים מִלְּהָרַע לְךָ: ולא ירא AND HE FEARED NOT — Amalek feared not אלהים GOD so as to refrain from harming you (Sifrei Devarim 296:7).