Let us embellish this thought. Of all the seventy nations of the world who hate Yisrael, why is it specifically Amalek who opposes the performance of teshuvah in the month of Elul? Why are they the ones who show up in the month of Elul to cool down the desire to perform teshuvah--"אשר קרך בדרך"—ignited by HKB”H?
We will now introduce a teaching from the Bnei Yissaschar (Tamuz-Av 1, 6). He cites the Megaleh Amukos on Vaeschanan (107) who brings down the Zohar hakadosh (Yisro 88b) that teaches that Yaakov and Eisav divided up the months of the year between them. As his portion, Yaakov Avinu took the first three months—Nissan, Iyar, and Sivan—for the realm of kedushah. The exodus from Mitzrayim took place in Nissan; then they prepared themselves to receive the Torah during the days of the Sefirah in the month of Iyar; in Sivan, they received the Torah at Har Sinai.
Correspondingly, Eisav chose the following three months as his portion—Tamuz, Av, and Elul. He was elated that he had control of the month of Elul, thinking that he could prevent Yisrael from performing teshuvah prior to the Days of Judgment. Yaakov Avinu, however, employed various tactics, waging a spiritual war against Eisav to gain possession of the month of Elul to enable Yisrael to utilize this month to perform effective, sincere teshuvah. This left Eisav only the months of Tamuz and Av, during which the two Batei Mikdash were destroyed.
Perhaps this explains why of all the nations, it was specifically Amalek, the grandson of Eisav, "אשר קרך בדרך"—who strenuously opposed the “derech” of teshuvah illuminated during the month of Elul. He wished to avenge his grandfather by taking back control of the month of Elul, which had been confiscated from him. Hence, we are cautioned: “Remember what Amalek did to you while you were departing from Egypt, how he happened upon you on the way, and he attacked at your rear, all the weaklings that straggled behind you.” These are words of chizuk from HKB”H, encouraging us to fortify our resolve not to allow Amalek to influence sinners to refrain from performing wholehearted teshuvah in the month of Elul.
Notwithstanding, we are the Children of Yisrael, the descendants of Yaakov Avinu, who believe in his kedushah and are entrenched in it. We believe that he was justified in taking the month of Elul away from Eisav, and this was condoned and sanctioned by HKB”H. Therefore, HKB”H—“Who provides a ‘derech’ through the sea”—illuminated the phenomenal “derech” of teshuvah in this month. In the merit of this teshuvah, the following will come true (Yoma 86b): "גדולה תשובה שמקרבת את הגאולה". It will hasten the arrival of the geulah—swiftly, in our times! Amen.
