Why does the Torah need to mention the fact that Moshe rebuked them only after he had captured Sichon and Og?
Rashi: Because otherwise, the people would have said 'What has he done for us? 1 He is incapable of taking us into the Land! So all he does is rail against us and find fault with us!' So he demonstrated his capabilities by overthrowing Sichon and Og before proceeding to rebuke them.
Seforno: He began to clarify the Torah after having attained for them 'a measure of Menuchah' (a small resting-place) in inhabited country. 2
Oznayim la'Torah: Refer to answer #1. So he waited until he had conquered the land of Sichon and Og, thereby opening the gateway to Eretz Cana'an - which Sichon and Og had blocked, 3 before rebuking them.
Oznayim la'Torah: Like we find by Dasan and Aviram, who said to him 'Af Lo el Eretz Zavas Chalav u'Devash Havi'osanu, ve'Lo Nasata lanu Nachalas Sadeh va'Kerem" - Korach, Bamidbar, 16:14. See Oznayim la'Torah, DH 'Acharei Hakoso' and see answer #3.
After having spent forty years in the desert.
See Oznayim la'Torah, DH 'Acharei Hakoso'.
Why does the Torah need to write " ... asher Yoshev be'Cheshbon" and " ... asher Yoshev be'Ashtaros ... "?
Rashi: Because, in addition to Sichon and Og's immense strength, Cheshbon and Ashtaros were were impregnable. Refer to Bamidbar 21:23:3:1.
Ramban: Because Cheshbon originally belonged to Mo'av, and Sichon captured it from them and made it his capital, and Ashtaros belonged to the Refa'im, and Og, who was king of the Emori, captured it from them. 1
Ramban: The Torah writes this with reference to Og's origin, because at this stage, he was no longer king of the Refa'im, but of the Emori - See Ramban DH 've'Inyan Sifri'. See also later 2:10 & 3:11, where he elaborates on the issue of the Refa'im.
What are the connotations of "Ashtaros"?
Rashi (citing the Sifri): It is synonymous with "Asht'ros Karnayim," 1 and has connotations of a hard rock.
Ramban: "Ashtaros was the name of a place, a strong fortified town 2 situated in the province of Edre'i.
Riva (citing R"M of Kutzi) and Hadar Zekenim (in 3:13): It is a place for grazing, This is why B'nei Gad and B'nei Reuven requested it! (Asht'ros Karnayim was between two tall mountains (like horns). The sun did not shine between them, so people brought flocks to rest in the shade there - Hadar Zekenim). 3
See Bereishis 14:5.
Ramban (citing Chulin, 84b) Commenting on "Asht'ros Tzoncha" - 7:13 - (See Rashi there): 'They are called 'Ashtaros' because they enrich their owners and fortify them, like those Ashtaros, which are strong rocks - See Ramban, DH 've'Lashon Sifri' & 'Aval Yitachen'.
Riva (Ibid.): Like "Asht'ros Tzonecha" - in Devarim 7:13, which Onkelos translates as 'Edrei Anach.'
What is the meaning of "Edre'i"?
Rashi (citing the Sifri): "Edre'i" is the name of the kingdom.
Ramban: See 1:4:3:2.
Why does the Torah need to mention the fact that Sichon dwelt in Cheshbon, and Og, in Ashtaros?
Rashi: To teach us that, not only were Sichon and Og invincible, but that their towns 1 were so well-fortified that, they too, were invincible.
What is the connection between Og and Ashtaros?
