Grappling with the commandment to obliterate the Nation of Amelek is an issue that concerns sensibilities. That the Torah would obligate us to destroy an entire nation, men, women and children is not an easy thing to understand or explain. On one level we must surrender our sense of moral rectitude to the Ratzon Hashem (Will of Hashem), and at the same time we have an obligation to try to understand the laws and values of the Torah as best as we humanly can. This can hopefully enable us to learn lessons from Mitzvot, even though we admittedly do not fully comprehend them.
The Torah describes Amalek’s attack on Bnai Yisrael as “Asher Karcha Baderech,” “that happened upon you on the way.” A number of Midrashim comment on the word “Karcha.” Rashi, quoting the famous Chazal, describes what Amalek did through the Mashal (Parable) of the hot bathtub, and how Amalek “cooled us down.” Additionally, Chazal see in this word Amalek’s belief that everything is attributed to “Mikreh,” “chance.” What these understandings have in common is that they attribute to Amalek this notion of “Bitul,” devaluing that which has importance. Am Yisrael had just been charged, by becoming the Am Segula, to bring meaning and the ultimate value to humanity. Amalek represents the devaluation of our role, as well as our connection to Hashem. The Gemara refers to Haman as “Boozi ben Boozi” which is not a comment on his drinking habits, rather that he inherited the Mida of “Bitul” from Eisav who denigrated the Bechora to Yaakov, when it says “Vayivez Eisav Et Habechora,” “And Eisav spurned his birthright.”
In his Sichot Mussar, Rav Chaim Shmulevitz traces the evil personified by Amalek to an earlier time. The Torah relates how Yaakov fled his parent’s house to Padan Aram after receiving the Brachot from Yitzchak. Chazal describe how Eisav dispatched his son Elifaz to kill Yaakov. Upon reaching Yaakov he was confronted by Yaakov with the treachery and evil deed he was about to commit. Elifaz replied that he in fact had a duty to carry out the murder in order to fulfill the Mitzva of Kibud Av. Although Yaakov deftly rescued himself by giving Elifaz all his money, Rav Chaim sees in the argument put forward by Elifaz the kernel that grew into Amalek. He exhibited the ability to twist and pervert the meaning of the Torah to justify our desires, even if it entails murder.