What did Hashem order Moshe to record?
Rashi: That Amalek was the first of all the nations to attack Yisrael.
Ramban and Seforno: To insert in the Torah Parshas Zachor (in Ki Seitzei). 1
Targum Yonasan: He ordered Moshe to record the battle with Amalek in the Book of Chronicles, in which the battles that were fought were recorded. 2
What is the significance of the ling-winded phrase "K'sov Zos Zikaron ba'Seifer"?
Megilah, 7a: In response to Esther's request to insert her Seifer in Kesuvim, the Chachamim Darshened "K'sov Zos"- refers to what is written here and in Ki Seitzei; "Zikaron" - to what is written in Nevi'im - when Yo'av fought Amalek, and "ba'Seifer" - refers to Megilas Esther, thereby permitting Megilas Esther to be included in Kesuvim. 1
See Torah Temimah, note 13, who elaborates.
What did Hashem instruct him to pass on into the ears of Yehoshua?
Rashi: He told him to instruct Yehoshua to command Yisrael to pay Amalek his dessert for being the first to attack Yisrael.
Rashbam: That he should fulfill the Mitzvah of destroying Amalek.
Vilna Gaon: He taught Yehoshua that the word "Zeicher" should be read accordingly. 3
To encourage them to take revenge.
Since he was a firsthand witness (Ramban).
And not "Z'char" (meaning the males of Amalek - to avoid the mistake of Yo'av (David ha'Melech's general), who misread the word and ended up leaving alive the Edomi women. Maharsha (Bava Basra 21a) - Yo'av thought that if even for a war of Mitzvah (Amalek), we kill only males, all the more so an optional war (Edom)!
Why did Hashem instruct Moshe to tell it specifically to the ears of Yehoshua?
Rashi: Because Yehoshua was destined to lead Yisrael into Eretz Cana'an. 1
A hint that it would be Yehoshua, and not he, who would be granted that privilege (Rashi).
What did Hashem mean when He said that He would destroy the memory of Amalek?
Seforno: He meant that He would destroy even his animals. 1
As Shmuel ordered King Shaul to do (See Shmuel 1, 15:3). See also Ba'al ha'Turim.
What are the implications of "Machoh Emcheh ... "?
Rashbam: It implies that it is Hashem's will that Amalek's name be erased.
Rosh: It implies that Hashem Himself will erase Amalek's name, because he (Amalek) stretched out his hand to destroy the Beis-ha'Mikdash. 1
Prior to that, it is incumbent upon us to do so - as the Torah states at the end of Ki Seitzei.
What is the meaning of "mi'Tachas ha'Shamayim"?
Sifri: It means that nothing will remain of Amalek - no child or offspring, no camel or donkey; so that nobody will be able to (point a finger and) say 'This belongs to Amalek'.
