(יז) זָכ֕וֹר אֵ֛ת אֲשֶׁר־עָשָׂ֥ה לְךָ֖ עֲמָלֵ֑ק בַּדֶּ֖רֶךְ בְּצֵאתְכֶ֥ם מִמִּצְרָֽיִם׃
(17) Remember what Amalek did to you on your journey, after you left Egypt--
(יח) אֲשֶׁ֨ר קָֽרְךָ֜ בַּדֶּ֗רֶךְ וַיְזַנֵּ֤ב בְּךָ֙ כָּל־הַנֶּחֱשָׁלִ֣ים אַֽחַרֶ֔יךָ וְאַתָּ֖ה עָיֵ֣ף וְיָגֵ֑עַ וְלֹ֥א יָרֵ֖א אֱלֹהִֽים׃
(18) how, undeterred by fear of God, he surprised you on the march, when you were famished and weary, and cut down all the stragglers in your rear.
(יט) וְהָיָ֡ה בְּהָנִ֣יחַ יְהוָ֣ה אֱלֹהֶ֣יךָ ׀ לְ֠ךָ מִכָּל־אֹ֨יְבֶ֜יךָ מִסָּבִ֗יב בָּאָ֙רֶץ֙ אֲשֶׁ֣ר יְהוָֽה־אֱ֠לֹהֶיךָ נֹתֵ֨ן לְךָ֤ נַחֲלָה֙ לְרִשְׁתָּ֔הּ תִּמְחֶה֙ אֶת־זֵ֣כֶר עֲמָלֵ֔ק מִתַּ֖חַת הַשָּׁמָ֑יִם לֹ֖א תִּשְׁכָּֽח׃ (פ)
(19) Therefore, when the Eternal your God grants you safety from all your enemies around you, in the land that the Eternal your God is giving you as a hereditary portion, you shall blot out the memory of Amalek from under heaven. Do not forget!
Commentaries on Deuteronomy 25:17
Plaut: Deuteronomy 25:17 -- Remember what Amalek did. The reference is to the events reported in Exodus 17:8-13. In Deuteronomic days, Amalek--a group of Nomadic tribes in the Negev and Sinai--no longer threatened the Israelites, but the memory of their first battle stamped Amalek forever as the archenemy whose weakened condition was doubtlessly seen as just retribution.
Alter: Deuteronomy 25:17 -- Remember what Amalek did to you. It is not entirely clear why Amalek is singled out as the archenemy of Israel. In historical terms, the Amalekites, a seminomadic people of the Negeb and southern trans-Jordan region, carried out frequent and brutal marauding raids against Israelite settlements. Deuteronomy here offers and explanation for the opprobrium of Amalek not mentioned in Exodus--that the Amalekites attacked the Israelite stragglers, who would have been the old, the infirm, and women and children, and slaughtered them.
Other place where Amalekites were talked about
Exodus 17:8-16 -- (8) Then came Amalek, and fought with Israel in Rephidim. (9) And Moses said unto Joshua: ‘Choose us out men, and go out, fight with Amalek; tomorrow I will stand on the top of the hill with the rod of God in my hand.’ (10) So Joshua did as Moses had said to him, and fought with Amalek; and Moses, Aaron, and Hur went up to the top of the hill. (11) And it came to pass, when Moses held up his hand, that Israel prevailed; and when he let down his hand, Amalek prevailed. (12) But Moses’hands were heavy; and they took a stone, and put it under him, and he sat thereon; and Aaron and Hur stayed up his hands, the one on the one side, and the other on the other side; and his hands were steady until the going down of the sun. (13) And Joshua discomfited Amalek and his people with the edge of the sword. (14) And the LORD said unto Moses: ‘Write this for a memorial in the book, and rehearse it in the ears of Joshua: for I will utterly blot out the remembrance of Amalek from under heaven.’ (15) And Moses built an altar, and called the name of it Adonai-nissi. (16) And he said: ‘The hand upon the throne of the LORD: the LORD will have war with Amalek from generation to generation.’
Commentaries on Deuteronomy 25:18
Plaut: Deuteronomy 25:18 -- Undeterred by fear of God. Which has no national limitation and obligates other peoples as well.
Stragglers in your rear. This aspect is not mentioned in Exodus. // Ancient armies often traveled with soldiers in front and their dependents in the rear; the norms of warfare generally forbade attacking the defenseless families--as the Amalekites did. Their heinous crime could be requited in kind (I Sam 15:2-3). // The noun נחשלים (necheshalim, translated as "stragglers") may originally have been נחלשים (nechelashim, enfeebled). Hence: those left behind. (Such transpositions occurred occasionally, and sometimes the transposed word remained as a variant of the original....)
Commentaries on Deuteronomy 25:19
Alter: Deuteronomy 25:19 -- when the LORD your God grants you respite from all your enemies. Historically, a campaign to wipe out the Amalekites was undertaken in the time of Hezekiel, in the late eighth century B.C.E.
you shall wipe out the remembrance of Amalek. The noun zekher, which is also used in the parallel verse in Exodus 17:15, means "name" but derives from the root meaning "remembrance." Etymologically, a name is the remembrance a man leaves after him, and zekher, "remembrance," is strongly linked with zekhar, "male." (Compare the necessity of male offspring to prevent a name from being wiped out in the levirate marriage.) But it is important to retain the idea of remembering in translation because the writer is pointedly playing with "remembrance...do not forget."
General Comments
"...Amalek is condemned for killing the weak and smiting the feeble because 'he feared not God.' This is evidently the reason why we were commanded to blot out the memory of Amalek since they came and fell upon the defenseless and weary without any pretext whatsoever. The Children of Israel were not entering their territory and it was purely a wanton attack. 'Amalek' against whom the Almighty declared eternal war is not any more an ethnic or racial concept but is the archetype of the wanton aggressor who smites the weak and defenseless in every generation." - Nehama Lebowitz
Kenneth J. Weiss, 2003 -- "In gematria, I discovered, Amalek and safeik (doubt) carry the same numerical value.... Since these words are numerically equivalent, can't we substitute one for the other? The message: in the wilderness our people repeatedly questioned the Holy One, challenged God's resolve in delivering them from the Egyptians. 'Remember what [doubt] did to you on the way...out of Egypt...how [doubt] fell upon you...and cut off all the weak ones at your rear' (Deut. 25:17-18 --R.E. Friedman). Torah (throught gematria) admonishes: Doubt is our Amalek within! It destroyed an entire generation!
Alan Cook, 2006 -- "What is the distinction to be made between the two injuctions that we are given regarding Amalek? What is the difference between זכור (zachor, 'remember') and לא תשכח (lo tishkach, 'do not forget')? זכור (zachor) implies that it is up to the indivdual who read (or hears) the words of כי תצא (Ki Teitzei) to personally take to heart the tale of the Amalekites and ensure that the enemies of the Jewish people do not prevail in his or her generation. Yet we have also been taught in our Haggadah, שלא אחד בלבד עמד עלינו לכלותינו (Shelo echad bilvad amad Aleinu l'chaloteinu, 'for more than one enemy has risen against us to destroy us'). Because our people has faced adversaries in every generation, we are called upon to ensure that the lessons of our ancestors' encounter with Amalek are not lost. This is the message of לא תשכח (lo tishkach): that we must teach our children about this episode."