Our Gemara on amud aleph discusses how the Land of Israel was allocated to the incoming generation of Jews as they completed their wandering of forty years:

Rabbi Yoshiya says: Eretz Yisrael was divided among those who left Egypt, as it is stated: “According to the names of the tribes of their fathers they shall inherit” (Numbers 26:55), which teaches that the Jewish people would inherit Eretz Yisrael according to the names of their fathers, i.e., those who left Egypt. 

Rabbi Yonasan says: Eretz Yisrael was divided among those who entered Eretz Yisrael, as it is stated: “Unto these the land shall be divided for an inheritance” (Numbers 26:53). But how do I realize the meaning of the verse: “According to the names of the tribes of their fathers they shall inherit” (Numbers 26:55)? 

Ben Yehoyada explains this dispute to be based on the circumstances and manner in which the Jewish people merited the land of Israel. He says, God told Avraham that his children would be enslaved for 400 years (Bereishis 15:13). Yet, we have a tradition (as it states in the Haggadah) that God shortened the time, and the Jews left Egypt after 210 years (see Rashi Bereishis 15:13). On what basis was the term of servitude reduced? Ben Yehoyada conjectures that There are two possible reasons. Either the intensity and suffering of the servitude was so great that they essentially accomplished whatever needed to be accomplished spiritually in half the amount of time, or they merited the land of Israel as a result of the faith they showed during the 40 years of wandering in the wilderness. Rabbi Yoshiya, who holds Eretz Yisrael was divided among those who left Egypt, is of the opinion that the Jews merited the land of Israel, as a result of the increased suffering in Egypt. That is why the land is allocated based on the Jews, who were part of the exodus. On the other hand, Rabbi Yonasan who holds Eretz Yisrael was divided among those who entered Eretz Yisrael is of the opinion that the Jews merited the land of Israel due to their faith and endurance during their wanderings of 40 years.

I believe this parallels a discussion about the basis for the final redemption, when the Maschiach arrives. In a fine article written by Rav Gavriel Kadosh, he reviews the two possible circumstances under which the Messiah will arrive. First, we see it represented in narrative in the scripture:

It states in circumstances under which the Messiah will arrive. First, we see it represented in narrative in the scripture:

It states in. Devarim (30) that after going through the various afflictions of exile, the Jews will take it to heart and repent, and God will save them. However, it states in Yechezkel (36) a narrative that seems to be predicated, not on repentance first. Rather, God will reach out to the Jewish people and purify their hearts and give them a new spirit and purify them. This second narrative indicates that the Messiah can come not prompted by repentance, but rather by God, choosing, out of love and mercy to redeem us regardless. We mights say then that Rabbi Yoshia required suffering and repentance in order for the Jews to merit the Promised Land, while Rabbi Yonasan held that they can become elevated by God promoting them to a new level, as they experienced the revelations at the Red Sea, Mount Sinai and the Clouds of Glory.  

A similar discussion takes place in Gemara (Sanhedrin 97b) about whether repentance is necessary for redemption, or will God out of mercy bring the Jews out of exile, and it seems that the dialogue ends with the latter opinion. In fact, Ramban (Devarim 32:2) States this explicitly, that there is no precondition of repentance ultimately.

On the other hand, Rambam (Laws of Teshuva 7:5) is unequivocal in stating that the Jewish people will only be redeemed via repentance. We may say this is typical of Rambam’s overall philosophical perspective that there are no shortcuts for spiritual elevation, and good intentions alone do not achieve what needs to be achieved in order for the soul to reach immortality. There must be an actual intellectual apprehension of wisdom and consonance with God’s will in order for the soul to be redeemed. (This is a complex discussion, but I will provide some references for you to study further: See Rambam, Laws of Kings 8:11, and Rambam commentary on the Mishna, Makkos 3:16.) Regardless, there is an optimistic and uplifting way of understanding the Rambam’s position, even if on the surface of it, it seems harsher than that of the Ramban. A careful reading of the words show that though penitence is a precondition, there is a prophecy and a promise that the conditions will result in leading the Jewish people to that state, so that they will be redeemed. In other words, the survival of the Jewish people,and their repentance are an ironclad guarantee. So, one way or the other, God has our back.

Translations Courtesy of Sefaria, except when, sometimes, I disagree with the translation

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