פרשת דברים תשכ"ח - סיחון ועוג

"To the tribe of Gad, for the various Gadite clans, Moses assigned [the following]: And it became their territory: Jazer, all the towns of Gilead, part of the country of the Ammonites up to Aroer..."

"But the Lord said to me: Do not fear him"

"Do not fear him" - this is [the meaning of] that which Scripture stated (Proverbs 28:14), "Happy is the man who always fears." And this is the trait of the righteous: Even though the Holy One, blessed be He, reassures them, they do not relinquish fear. And so [was it] with Jacob - "and Jacob feared" (Genesis 32:8). Why did he fear? He said, "Maybe I have been tarnished by something [\I did when I was] with Laban... so the Holy One, blessed be He, abandoned me." And so too did Moses take hold of fear corresponding to his [fore]father. And why did he fear? He said, "Maybe Israel misappropriated [some goods] in the war with Sichon or became tarnished with a sin." The Holy One, blessed be He, said to him, "Do not fear."

... But according to the simple understanding, Moses did not now have in mind to grant the land of Sichon and Og to Israel... And behold, Sichon came out into the desert to face Israel and to fight with them against their will. Then God informed [Moses] (Deuteronomy 2:31), "See, I have begun to give Sichon and his land in front of you; begin and possess it" - as he began the conquest of the seven nations from here. But Og gathered his troops to Edrei, which is at the tip of his border, so Israel could have veered away from him, as they veered away form Esau. But God said to him, "Do not fear him."

Fear and trembling struck Moses and all of Israel when they thought that Og was coming out to meet them after [their] victory [over] the king of the Amorites. [They thought] that it could only be that his heart swelled with valor and that his heart was impassioned to take vengeance for Sichon.