“And Moshe went” (D’varim 31:1). Where did he go? The verse continues, “and he spoke these words to all of Israel,” leading Ibn Ezra to say, “he went to each and every Tribe” to give them words of encouragement and/or to bless them. However, Ba’al HaTurim connects these words with the words of the preceding verse, which mentions our forefathers, Avraham, Yitzchok and Ya’akov, in the context of G-d having made an oath to give them the Promised Land; “he went to them to tell them that G-d had fulfilled His oath and brought Israel into the land.” Although not the straightforward intent of the verses, since the Torah speaks on numerous wavelengths simultaneously, this “trip” is also being hinted to, based on the proximity of these two verses.
Several commentators ask how Moshe could have relayed this message to the Patriarchs if the Children of Israel didn’t enter the Promised Land until after he died. Rabbi Yitzchok Sorotzkin, sh’lita (Rinas Yitzchok III), discusses whether having conquered the land of Sichon and Og was enough to be considered having fulfilled the oath, tying it into whether the vow not to let Moshe enter the Promised Land was nullified when this land was conquered (and then assigned to some of the Tribes, seehttp://rabbidmk.wordpress.com/2010/07/21/parashas-va-eschanan-5770/). After all, if this land was also considered the “Promised Land,” Moshe was there when it was conquered, and could relate this to our forefathers. Rabbi Sorotzkin dismisses the idea based on Gur Aryeh (D’varim 3:23) saying that the oath (not to let Moshe enter the land) was referring to the land west of the Jordan River, but there’s another reason why that must be the land Moshe told the Patriarchs their descendents had entered. Although Moshe actually informing them of this is hinted to in these verses, G-d made his request of Moshe as He was showing him the land from atop Mt. Nevo (see Rashi on 34:4). Since it was “this land” Moshe was asked to tell them about, and “this land” referred to the land west of the Jordan, it could not have been the land already conquered that Moshe was supposed to tell our forefathers about. Which brings us back to the question of how he could do so if he died before it happened.
Tz’ror HaMor (34:3) suggests G-d was telling Moshe “after you saw [the land] with your own eyes and you set your eyes upon it with benevolence and prayed about it, [it is as if] they (the Children of Israel) have taken hold of it in your merit.” Therefore, “you can tell the Patriarchs that I have fulfilled the oath and given it to them” even before they are physically in the land. B’er BaSadeh (34:4) compares it to when G-d told Moshe He had already begun to give Sichon and his land over to him (31:2) even before the war had started. Rashi explains how the land could be considered conquered prior to it actually happening: G-d “subdued the administering angel of the Emorites under Moshe’s feet, and he stepped on his neck.” Here too, when G-d told Moshe “I have shown it to you with your eyes,” it meant in the spiritual realm, showing him that the administering angels of the seven nations of Canaan were subdued. Therefore, Moshe was able to tell the Patriarchs that it had already been accomplished.
When Ba’al HaTurim tells us that the last verse of Parashas Nitzavim and the first verse of Parashas Vayeilech are telling us that Moshe went to our forefathers to give them the information G-d had asked him to relate, he continues by saying, “and the Midrash says that from here we learn that the dead talk with each other.” Obviously, then, Moshe didn’t actually tell them until after he had already died. [Even without this being stated explicitly in the Midrash, how could Moshe have relayed the message to them while he was alive — especially since they are buried in Chevron, where Moshe was forbidden from going. Did his “virtual tour” of the Promised Land include being able to speak to them when he “visited” Kiryat Arbah?] Since Moshe didn’t speak with Avraham, Yitzchok and Ya’akov until after he died, there is no reason to assume it happened before he could accurately tell them that G-d had fulfilled His promise and their descendants had actually entered the land.