Rabbi Sholom Twerski
August 21, 2026
At the end of this week’s parsha, we are charged with the mitzvah of destroying Amalek. In the sefer Divrei Yosef, he addresses a question which arises from our first encounter with Amalek. There, Moshe appointed Yehoshua to be the one in charge of fighting Amalek.
וַיֹּאמֶר מֹשֶׁה אֶל־יְהוֹשֻׁעַ בְּחַר־לָנוּ אֲנָשִׁים וְצֵא הִלָּחֵם בַּעֲמָלֵק
Moshe said to Yehoshua, “Pick some troops for us, and go out and do battle with Amalek…”
Why was Yehoshua specifically which was given this task?
The Baalei Tosafos on Chumash point out that when it comes to warring with Esav, the concern we have is his z’chus of Kibud Av v’Eim. We know that this was a mitzvah that he excelled in. When it comes to Amalek, this z’chus is highlighted because their entire point of attack is based on that mitzvah.
There is a famous medrash that Esav sent his son, Elifaz, to kill Yaakov. Instead of killing him, Elifaz confiscated his money, causing Yaakov to become destitute, which was akin to killing him.
Tosafos provide us with the continuation of that story. When Elifaz came back though, Esav was not impressed with this loophole. Determined, he sent his grandson, Amalek, to kill Yaakov. Amalek swore he would but Timna, his mother, convinced him to delay. The reason was based on the Bris Bein Habasarim, where Avraham’s grandchildren were foretold to undergo many years of harsh slavery. Would Amalek kill Yaakov, that prophecy would necessarily have been fulfilled through Amalek. Therefore, say Tosafos, immediately upon Klal Yisroel’s redemption from Mitzrayim, Amalek went about fulfilling the oath he had given to his grandfather, Esav, to wipe out Yaakov.
This can help explain why Yehoshua was chosen to lead this war. Most of Klal Yisroel carry a deficiency in the area of Kibud Av v’Eim. Because of the Mechiras Yosef, the sale of Yosef, Yaakov was in mourning and deep pain for many years. Yosef, however, being the victim, was not at fault and did not have this blemish on him.
Furthermore, Yosef’s enslavement and exile were themselves a tikkun, or repair, for Yaakov’s own lack in this regard. Chazal view the 22 years that Yosef was separated from Yaakov as an atonement for Yaakov’s separation from his parents when he went to Charan until he returned.
So, Yehoshua, who was a descendant of Efraim, son of Yosef, was the prime candidate to lead the war against Amalek, for he did not have the lack of Kibud Av v’Eim which may have hindered their success in the battle against Amalek.
That is also why, continues the Divrei Yosef, we find the expression of צֵא used in connection with this war as it says, “וְצֵא הִלָּחֵם בַּעֲמָלֵק”. Wouldn’t it be obvious that one would have to go out to war? Surely, it wouldn’t be waged in the living room!
By the giving of the brachos, Yitzchak told Esav, “וְעַתָּה שָׂא־נָא כֵלֶיךָ תֶּלְיְךָ וְקַשְׁתֶּךָ וְצֵאהַשָּׂדֶה וְצוּדָה לִּי [צָיִד]׃”. Now, Esav didn’t really have to go out to the fields to capture game. He had the special clothing of Adam HaRishon which, when worn, caused all animals to come to him! Yet, to fulfill the dictates of his father to the maximum, he left his special clothing with his mother and went out to the field to hunt the animals needed to prepare the food. This highlights his special attention to the mitzvah of Kibbud Av.
To counter that, Moshe Rabbeinu uses the same expression- צֵא. We will overcome the unique merit of Esav by going out headed by Yehoshua, descendant of Yosef, that possesses this merit, too, of Kibbud Av v’Eim.
R’ Aryeh Leib Shteinman was asked why we see that these last few generations have a lifespan longevity that we haven’t seen in centuries. He answered that in order to get out of the galus of Edom, which is Esav, we need to bolster our merit of Kibbud Av v’Eim. Hashem therefore grants more years so Klal Yisroel will have the merit of many years of honoring and respecting our parents and taking care of them.
May our attention and care for this special mitzvah bear fruit and may we see the end of the galus soon.
Have a wonderful Shabbos!