Timna did not have an easy time carrying out her request to join the family of Avraham Avinu. Chazal teach that Timna, sister of Lotan, daughter of Seir, aluf of Eisav, king of the Chorim, was a princess who had it all – luxury, honor, material satisfaction. Yet, she rejected her pagan upbringing, choosing instead the G-d of Avraham. They (the descendants of Avraham) refused to accept her, due to her Canaanite lineage. The bloodlines are very important to us, and Canaan just was not a nation to which we wanted to attach ourselves. (They certainly saw negative traits in her, or felt that her motives for converting were questionable.) Timna approached Yaakov Avinu with her request for conversion. The Patriarch said that he could not do it. She thought that one of the Shevatim, Tribes, would acquiesce to her request. They adhered to their father’s ruling: the answer was no.
Out of desperation, Timna approached Eisav. (This, in and of itself, is indicative of her misguided motives. One does not join with Eisav under any circumstances. His relationship with the Patriarchal family was biologic. One does not attach himself to evil incarnate, regardless of his pedigree.) Eisav was not interested, claiming that he already had three wives. A fourth wife was not an idea that he was prepared to entertain. Her next encounter was with Elifaz, Eisav’s son, his “pride and joy,” with whom she pleaded that he accept her as a wife. He agreed to take her as a pilegesh, concubine – not as a wife. She became quite frustrated and embittered after being scorned by so many members of the Abrahamic family; nonetheless, she agreed. The product of the union between Elifaz and Timna, his concubine, was none other than the archenemy of the Jewish People: Amalek.
Two parents who were without clear spiritual direction. Elifaz was the son of Eisav, but a student of Yaakov. Timna, a princess who had it all, was willing to reject it for a connection with Avraham’s family, who, when she could not realize her objective, settled to become Elifaz’s concubine. Two parents who were spiritually disjointed imparted their befuddled mindset to their son. Is it any wonder that he ended up feeling so loathsome towards what he thought was the source of his parents’ irrational frustration with religion?
Horav Shimon Schwab, zl, posits that Amalek grew up in a home where he sensed, and was witness to, his mother’s frustration. He was well-aware of the sham of idol worship. He understood that the stones they called deity were powerless. Nonetheless, despite the fact that he knew that Hashem was the true Creator, he was prepared to go to battle with the Almighty’s will and use His People as the scapegoat – all to avenge his mother’s frustrations and helplessness. Chazal characterize him as a rasha, wicked person, “who knows the greatness and Omnipotence of Hashem, and, in spite of that, deliberately goes against His will.” As a result of this detestable behavior (which was rooted in the anger he had over his mother’s rejection and ensuing frustration), Amalek went down in history as the only nation whose memory we are commanded to eradicate.
Many entities have sinned against Hashem, such as the moon that complained that it and the sun could not give light equally. Hashem diminished the moon’s light. The earth swallowed/absorbed Hevel’s blood and did not heed Hashem’s command to give forth (trees with) bark that tasted like its fruit. In the future, however, Hashem would forgive the moon and the earth.
The nachash, serpent, violated Hashem’s command and convinced Chavah to eat of the fruit of the Eitz HaDaas, Tree of Knowledge. He lost his feet and must now slither as atonement for his sin. The Maharsha explains that the nachash was not absolved of its sin (as were the moon and the earth), because the nachash knew Hashem’s plan and went against it. The nachash was to be subservient to Adam and Chavah. He would provide the physical/material endeavors, i.e., food and nourishment, while they would be free to live on a spiritual plane. The nachash reneged. He, too, wanted to live a spiritual life. Why should he be a “slave” to Adam and Chavah? He took the approach that was later negatively perpetrated by Amalek: “knowing the will of Hashem and deliberately violating His plan.” For such action, there can be no forgiveness. Thus, the nachash will continue slithering forever, and Amalek will live with his self-loathing, and they and others like them, who know and are cognizant of Hashem’s will, will never achieve Heavenly absolution. Their sin connotes the greatest degree of chutzpah, for which there can be no leniency.