What are the connotations of "Hinei Anochi Shole'ach Mal'ach"? Who is the Mal'ach that Hashem will send ?
Rashi (in Pasuk 21) and R. Bachye #1 (according to Kabalah): It refers to Matatron 1 ('the Minister of the Interior' ? R. Bachye) ? belonging to the group of angels that do not sin.
R. Bachye #2 (citing R. Chananel): It refers to Micha'el, the great minister, who protects Yisrael. 2
Da'as Zekenim #1 and Hadar Zekenim #1: On the merit of the Aseres ha'Dibros, which begin with the word "Anochi" ('I'), Hashem said 'I will send an angel to guard you'.
Da'as Zekenim #2 and Hadar Zekenim #2: "Mal'ach" refers to the hornet, 3 which Hashem will send [to help Yisrael conquer Eretz Yisrael].
Hinted in the words "Lish'morcha ba'Darech" ? Onkelos translates "Mishmeres" as 'Matras'. See R. Bachye on p. 246 who elaborates, and R. Chavel's footnotes. Refer also to 23:21:3:3.
Hinted in Pasuk 23 "Ki Yeilech Mal'achi Lefanecha" ? "Mal'achi" spells 'Micha'el'. See R. Bachye here and in 24:1, who elaborates.
See Da'as Zekenim and Hadar Zekenim.
Rosh: Because "Mal'ach" sometimes refers to a Navi, like we find in Divrei ha'Yamim 2 36:16 "Vayih'yu Mal'ivim be'Mal'achei Elokim".
The commentaries explain that Moshe stood-in for the Mal'ach, who appeared to Yehoshua shortly after Moshe's death ? Rashbam: As the Ma'lach himself said to Yehoshua "Atah Ba'si" (Yehoshua 5:14)
Why did Hashem inform Yisrael that a Mal'ach would bring them to Eretz Yisrael and not He Himself?
Rashi, Ramban (citing Midrash Rabah) and R. Bachye #1: He was telling them that they would sin (with the Golden Calf), 1 and that He would therefore not go in their midst, but send an angel in His place
R. Bachye #2 (citing Midrash Rabah): Had Yisrael merited, Hashem Himself would have been the Shali'ach, just as He had led them Personally up until then; 2 But now that they were no longer worthy, (because they sinned by the Eigel) He sent a Mal'ach.
If Hashem was referring to the angel that He would send after the sin of the Golden Calf, why did Yisrael not become dejected and why did Moshe not object as they did when it occurred (See Ki Sisa, 33:3 & Rashi Ki Sisa, 33:12)?
Oznayim la'Torah: Because, whereas in Ki Sisa, the Torah is talking about after the sin of the Golden Calf, where Yisrael and Moshe were worried that hey would sin and the Mal'ach would not forgive them, as Hashem had warned them, the current Parshah is talking about the period following Matan Torah, where even Hashem atterted that they had reached the highest levels, 1 they were certain that they would not sin, and there was no reason to be concerned.
Oznayim la'Torah: See Tehilim, 82: 6.
What are the connotations of the words "El ha'Makom asher Hachinosi"?
Rashi #1, Ramban, Targum Onkelos and Targum Yonasan: It means to the location 1 that Hashem designated.
Rashi #2: It is one of the Pesukim which teaches us that the Beis-Hamikdash in Heaven is located exactly opposite the Beis-Hamikdash on earth. 2
Of His Shechinah (Targum Yonasan), with reference to the Beis-Hamikdash, as the Pasuk indicates in Beshalach, 15:17 (Ramban).
Oznayim la'Torah: And a Mal'ach did indeed show Gad ha'Navi the exact location - the barn of Arnon on the Har Hamoriyah, where the Beis-Hamikdash shel Matah was to be built. Moreover, if the Mal'ach was Micha'el, as some commentaries explain, it was most appropriate, since Micha'el is the Kohen Gadol who sacrifices the Neshamos of Tzadikim on the Mizbe'ach shel Ma'alah.


