Which donkey is "ha'Chamor" referring to?
Rashi: This is a special donkey - the same donkey on which Avraham rode to the Akeidah, and on which Mashi'ach will be riding when he reveals himself to Yisrael. 1
Rashi (to Bereishis 31:17) points out that when Yaakov travelled, he placed his sons before his wives (as opposed to Esav, who placed his wives first (Bereishis 36:6).) If that is proper conduct, why did Moshe seat his wife on the donkey, before his sons?
Gur Aryeh (to Bereishis 31:17); Moshav Zekenim (to Bereishis 36:6): Moshe's children were infants, and needed their mother.
Seeing as at this point, only Gershom had been born (see above, Shemos 2:22), why does the Torah write that Moshe took his sons (plural)?
Ramban #1: The Torah sometimes refers to a single person in the plural. 1
Ramban #2: Eliezer was born the moment Moshe returned to Midyan. He neither circumcised him nor gave him a name at that stage, because he was busy with Hashem's command to go to Egypt on his special mission. 2
Targum Yonasan: Refer to 4:24:2:4.
Ramban: See, for example, Bamidbar 26:8. Tziporah must have either become pregnant with Eliezer on the way to Egypt, or in Egypt, assuming that Moshe took her there.
Ramban: And it was only when he arrived in Egypt and saw that he had been saved from all those who sought his soul, that he appropriately called him Eliezer.
Why does the Torah mention that Moshe took the staff, after writing that he returned to Egypt?
Rashi: To be sure, he took the stick before leaving for Egypt! The Torah does not always follow the chronological sequence. 1
Seforno: The beginning of the Pasuk is referring to Moshe's returning to Yisro from the desert. 2 Then the Pasuk tells us that after depositing his wife and children with his father-in-law, he returned alone to Egypt, having taken his staff with him. 3
Gur Aryeh: What is bothering Rashi, is that Moshe must have taken the staff before returning to Egypt! We should learn the verses (4:20-21) in the following sequence - 'Moshe took his wife and children and settled them on the donkey, and Moshe took the staff of G-d in his hand. Hashem said to Moshe, 'As you go to return to Egypt....' And he returned to the land of Egypt.'
Though chronologically, it is not clear how this fits in with the previous Pesukim.
If Moshe took his wife and sons with him to Egypt, as the Pasuk implies, how is it that, at the beginning of Parshas Yisro, Yisro brought them to Moshe from Midyan (18:2-4)?
Rashi (to 18:2): When Aharon met Moshe at Har Sinai, he questioned the wisdom of Moshe taking his wife and children to Egypt, so he sent them back.
Ramban #2 (citing the Ibn Ezra): Initially, Moshe did indeed take Tziporah and his sons with him. However, when the incident recorded shortly after (Shemos 4:24-26) occurred, it was not possible for them to continue to travel; so, not wanting to delay fulfilling Hashem's command, he left them in the inn with instructions that, when Eliezer will have recovered, they should return to Midyan. 1
Ramban #3: He actually took them to Egypt. 2 However, after they had been there for some time, she longed to return home, so Moshe sent her back. 3
Seforno: Moshe did not bring them to Egypt. Refer to 4:20:3:2.
Hadar Zekenim (to 18:2): Moshe brought them to Egypt, and Yisro took them back to Midyan, to be with him.
Ramban: As is hinted in the words "after he sent her away" (Shemos 18:2).
Ramban citing the Midrash: In fact, Yisro advised Moshe to leave them in Midyan, but Moshe insisted on taking them with him - so that they should not miss Ma'amad Har Sinai. Yisro conceded to Moshe, and Hashem corroborating Moshe's decision, ordered him to return to Egypt with his wife and children.
Ramban: As is hinted in the words "after he sent her away" (Shemos 18:2); only Yisro was afraid that Moshe's intention was to divorce her. Also refer to 4:19:2:1 and its note.
Why does the Torah not mention the birth of Moshe's second son, nor the reason for his name, in our section (but rather in Parshas Yisro, Shemos 18:4)?
Ramban #1: In fact, in spite of the term "Banav," only Gershom had already been born, and Tziporah became pregnant with Eliezer on the way to Egypt or in Egypt, assuming that she actually went there. 1
Ramban #2: Although Tziporah was pregnant with Eliezer, he was born only after Hashem spoke to him by the Burning Bush. And because Hashem's command was incumbent upon him, he did not circumcise him before departing for Egypt; nor did he manage to name him after circumcising him due to the incident with the angel. And it was only after he arrived in Egypt and discovered that he was no longer threatened by those who sought his Soul that he named him Eliezer - "Because the G-d of my father assisted me..." (18:4).
QUESTIONS ON RASHI
Rashi writes: "'On the donkey' - The special donkey; the donkey that Avraham saddled for the Akeidah, and upon which Mashiach will be revealed...." How can riding on any donkey be "special"? Why were Avraham, Moshe and Mashiach singled out to ride on it?
Gur Aryeh #1: 'Riding' symbolizes loftiness, just like a rider sits over the animal. 1 Avraham, Moshe and Mashiach are unique in their greatness, raised high over everyone else. 2 All others are subservient to them. 3 Thus, 'they rode the same donkey.'
Gur Aryeh #2: The donkey is the most straightforward of all animals; its very name means Chomer (physicality). 4 When these three Tzadikim are portrayed as riding upon the simple Chamor, 5 the contrast highlights their loftiness to the greatest degree possible. 6
Maharal: Refer to 4:20:1.4:4.
Rav S. R. Hirsch (to Bereishis 1:24): The word 'Behemah' (animal) is connected with the word 'Bamah' (stage, podium). Domesticated animals shoulder man's burdens, absolving him of physical labor, and freeing him to pursue loftier matters.
Gur Aryeh: Chazal describe Avraham and Moshe as 'raised above the sky' (or the stars) (see Rashi to Bereishis 15:5, and Rashi to Shemos 9:22). Mashiach will be even higher still. Also see Maharal (Gevuros Hashem, Ch. 29, p. 114), and refer to 1:22:2.3:2.
Gur Aryeh: Avraham, more so than the other forefathers, was accepted by all nations as "Prince of G-d" (Rashi to Bereishis 14:7); his name means "father of a multitude of nations" (Bereishis 17:4). Moshe ruled Yisrael, did whatever he pleased in Pharaoh's palace, and defeated Sichon and Og. And in the future, all nations will bring Mashiach tribute (Rashi to Bereishis 49:10).
Gur Aryeh: It is therefore first among the non-Kosher animals, and the only one with the Mitzvah of Bechor (first-born).
Gur Aryeh: Although the horse is a more respectable animal from a worldly perspective, the point here is to emphasize the Tzadikim's greatness from a G-dly perspective.
I heard in explanation, that every animal has certain characteristics. "Riding" on that animal means using those traits to achieve one's goals. A donkey (Chamor), however, is simpler, in that it negates itself completely to its rider, with no self-expression. Thus, 'riding on a Chamor' means showing the loftiness of one's Tzelem Elokim, harnessing Chomer towards one's needs, giving it Tzurah. (EK) (For explanation of this common terminology in Maharal, refer to 1:1:2.8:1* and 1:1:2.9:1*.)
Rashi writes: "The special donkey; the donkey that Avraham saddled for the Akeidah, and upon which Mashiach will be revealed...." Chazal (Pirkei d'R. Eliezer 31) add that this donkey was created during Bein ha'Shemashos (twilight) of day six of Creation (along with other miraculous items, listed in Avos 5:6). Why did it need to be created then?
Gur Aryeh: It was not the donkey itself that was special, but these three Tzadikim, and how they "rode" upon it; i.e. that they rose above nature (refer to 4:20:1.1:2). The special items created at twilight of the sixth day of Creation seem to be natural, yet they are a bit above nature. It was fitting for these three Tzadikim, who reached such G-dly levels, that they not ride an ordinary Chamor of the six days of Creation and its natural order, but rather a miraculous one of Bein ha'Shemashos.
Maharal (Derech Chayim p. 236, to Avos 5:6): Bein ha'Shemashos is neither day nor night. The twilight of day six of Creation was already leaning towards Shabbos; such that time was already more sanctified than the six preceding days. It was not fitting that ordinary, natural things be created then; and yet, something had to be created, for [in truth] it was not yet Shabbos. That is why the miraculous was created just then.
Rashi writes: "The special donkey; the donkey that Avraham saddled for the Akeidah, and upon which Mashiach will be revealed...." Could this same donkey have lived for so long?
Gur Aryeh: Chazal do not mean this literally! Rather, it was at Bein ha'Shemashos that the potential was set in motion to rise above nature (see 4:20:1.1:2). This potential would be actualized at the appropriate times.
Rashi writes: "The special donkey; the donkey that Avraham saddled for the Akeidah, and upon which Mashiach will be revealed...." What is the connection between Avraham, Moshe and Mashiach in this respect?
Maharal #1 (Gevuros Hashem, Ch. 29, p. 115): All three share a parallel purpose, thus they conceptually are one. All three would be uplifted over the rest of the world (see 4:20:1.1:1).
Maharal #2 (ibid.): The individual person has three abilities that are distinct from the physical body, and transcend it - Chochmah, Binah and Da'as. So too for the greatness of Mankind in history. Chochmah was personified by Avraham, who "intuited Torah from his kidneys" (Bereishis Rabah 61:1). Binah is exemplified by Mashiach (Yeshayahu 11:2). Da'as was Moshe, who knew the Unique Name of Hashem.
Maharal #3 (ibid.): Avraham represented the power of Zechirah (remembrance - as in Tehilim 105:42). Mashiach represents Mishpat (justice, as in Yeshayahu 11:4). Moshe's power was Chochmah, who attained 49 gates of Binah.
Maharal #4 (Derush Al ha'Torah (end), p. 49): At these three junctures in history (prior to Avraham, Moshe and Mashiach), the world was empty of any wisdom - just like a donkey! Avraham proclaimed the name of Hashem before all of mankind; and Moshe brought the Torah down to the world. Mashiach will fill the world with Da'as (Yeshayahu 11:9), at a time that the Torah had been forgotten. Each "rode on a donkey" in the sense that they led the world at a time that had been devoid of wisdom. 1
Also see Oznayim la'Torah, who connects the three occasions on which the donkey was ridden.