What did Moshe mean when he said "Asher Yeitzei lifneihem"?
Rashi: He meant not like the kings of old, who sat at home and sent their armies to war, but like he did, when he fought against Sichon and Og. 1 as the Pasuk states 2
Seforno: He was referring to leading the people in wartime, whereas "Va'asher Yotzi'em" he said with reference to leading them in matters concerning state.
As the Pasuk records In Chukas, 21:34.
Rashi: And indeed, this is what Yehoshua (See Yehoshua, 5:13) and later David (See Shmuel 1, 18:16), did. See also Rashi in Yehoshua, 7:10 ? regarding what happened the one time when Yehoshua failed to do so.
What did Moshe mean when he added "Va'asher Yotzi'em va'Asher Yevi'em"?
Rashi #1: He meant that Hashem should pick someone who was sufficiently worthy to take Yisrael to war and to bring them back on his merit.
Rashi #2: "Va'Asher Yevi'em" means that the new leader should merit to take Yisrael into Eretz Yisrael, and that he should not suffer the same fate as Moshe himself did, in that he did not merit to do so.
Riva citing R. Tam of Orlins: This refers to the Urim v'Tumim. 1
Seforno: Refer to 27:17:1:2.
Here we discuss the new leader! Perhaps he hints that the leader will ask from the Urim v'Tumim. Hadar Zekenim (27) implies like this. (PF)
