The Torah portion of Va’et’chanan begins with Moshe Rabeinu’s prayer to enter the Land of Israel, as Moshe said,
“Please, allow me to cross over and see the good land that is across the Jordan, this good mountain and the Lebanon.”
According to Rashi, “this good mountain” refers to Jerusalem, which was called a “mountain” by both Avraham Avinu and Isaiah the prophet. Moshe had already called Jerusalem a mountain in the Song of the Sea when he said,
“You will bring them and plant them on the mountain of Your inheritance, the place for Your habitation, which You, G-d, have made.”
The Deepest Torah Is in Jerusalem
Rabbi Naftaly Tzvi Berlin explains (in Ha’amek Davar) that the Land of Israel is called “good” because it’s a land which nurtures a higher level of Torah study. (The Torah is called “good,” as it says, י אַל תַעֲזֹבוכִּי לֶקַח טוֹב נָתַתִּי לָכֶם תוֹרָתִּ ּ – “For I give you good instruction; do not forsake my Torah.”) Similarly, Jerusalem is called “the good mountain” because it engenders an even deeper level of Torah study, as the verse says, כִּי מִּצִּיּוֹן תּµצּµא תוֹרָה וּדְבַר ה' מִּירוּשָלָ ִּם – “For Torah shall come forth from Zion and the word of G-d from Jerusalem.” Based on this, the reason Moshe wanted to enter the holy land and the holy city was to be able to plumb the depths of the Torah.
Entry for Eternity
Another reason Moshe wanted to enter the land is that if he would enter, the Beit HaMikdash could never be destroyed as his presence in the land would have inspired the Jews for generations to come to remain loyal to G-d Almighty. Moshe alluded to this by calling Jerusalem “טוֹב” (good) which, when counting the hidden letters, has the gematriyah (numerical value) of 853. This is the number of years that the Jewish people needed to stay in the land in order to remain there eternally. In fact, they were exiled after 850 years. Had Moshe been there, they would have led righteous lives and, after being there for 853 years, would never have had to leave.