Rabbi Ethan Tucker, Facing Amalek, Facing Ourselves
This shadowy connection between Efraim and Amalek runs deeper. Efraim is Yitzhak’s great-grandson, through the line of Ya’akov. Amalek is also Yitzhak’s great-grandson, through the line of Esav (Bereshit 36:12). Amalek is therefore a direct descendant of Avraham Avinu as well.
Perhaps this is the sense of the tantalizing statement that אין זרעו של עמלק נופל אלא ביד בנה של רחל. (Pesikta Rabbati 13) 'Only a child of Rahel can defeat Amalek’s line'; Yehoshua, Shaul, Mordechai and others must confront Amalek because Amalek is their mirror image and only a person himself can slay his own shadow.
Amalek is closer to us than we like to think. Amalek is the path not taken, Israel’s doppelganger in history, reflecting what might have been and what is still always possible if we lose our way. The holy war against Amalek is thus always also one against our own failings, the recognition that our own missteps can ultimately come back to haunt and debilitate us. Amalek is thus not only significant as a historical people, but perhaps even more prominently as a specter of what Jews and Judaism can become if they stray from the correct path.
זכור את אשר כו' ואתה עיף ויגע ולא ירא אלקים (דברים כה, יז-יח). נראה, דהנה לא זו בלבד דזרע ישראל הם מצווים על מחיית עמלק דהוא זרע עשו אלא דכל איש מישראל צריך למחות חלק רע המכונה בשם עמלק אשר טמון בלבו דכל זמן דזרע עמלק נמצא בעולם אז כיון דאדם גם כן הוא עולם קטן אז יש מציאות לעמלק לכח הרע בכל אדם אשר מתעורר בכל פעם להחטיא את האדם ועל זה בא הזכירות בתורה.
Remember what etc you were famished and weary, and cut down all the stragglers in your rear: he did not fear God. (Deut. 25:17-18) It seems, that it is not only for this that the seed of Israel is being commanded regarding the erasing of Amalek, which is from the seed of Esav. Rather, every person in Israel needs to erase the evil part that is concealed in one's heart, that is known by the name Amalek. This is because whenever the seed of Amalek is found in the world it is found in the human being, since the human is a small world, and therefore there is a reality to "Amalek", to the force of evil inside every human being, which arises every time to make a human being sin, and is regarding this that the remembrance comes in the Torah.
Rabbi Francis Nataf
When the Torah tells us that the nation of Amalek did not fear God, it is saying that they were unrestrained by any concept of a higher power and thus possessed an unusual lack of common decency. They were the most extreme manifestation of this attitude. Their pirate-like behavior reflects a lack of respect for man’s uniqueness and ultimately for the power that stands behind it. No wonder, then, that the Jews are commanded to blot out Amalek. They represent an antithesis to the Jewish nation’s mission in the world, and their approach to life presents a formidable obstacle to the Jewish people’s goal of establishing a kingdom of God on earth.
The fight against Amalek does not end when the nation is destroyed, for even when it would be defeated its legacy would likely remain. As long as greed exists in the human heart, there will always be a need to fight against the temptation to view others as mere objects standing in the way of one’s advancement. The eternal struggle against Amalek is how Judaism formalizes this need.
[Redeeming Relevance in the Book of Deuteronomy: Explorations in Text and Meaning, Urim publications, 2016 - Chapter 6]