Moses’ greatest desire was to enter the Promised Land along with the Israelite nation whom he had led across the wilderness. Sadly, it did not happen. Moses died and was buried shortly before the Israelites crossed over the Jordan.
There is a great deal of discussion and debate among the commentators as to the deeper, more philosophical reasons why Moses could not enter the Promised Land, but the most basic reason is the one recorded in the Book of Numbers: “And the Lord spoke to Moses and Aaron, ‘Because you did not believe in me, to sanctify me in the eyes of the Children of Israel, therefore you will not bring the congregation into the land that I have given them” (Numbers 20:12). God thus rebukes Moses and Aaron immediately at Meribah, after they struck the rock to get water rather than speak to it as God had instructed (ibid 20:7-11).
According to the Midrash, the real issue was not that Moses or Aaron doubted God, but that they acted in a manner that might lead others to doubt God. The Midrash explains the situation with a parable comparing the situation, to a “case of a king who had a friend. Now this friend displayed arrogance toward the king, privately using harsh words. The king, however, did not lose his temper with him. After a time, he [the friend] rose and displayed his arrogance in the presence of his legions, and the king passed sentence of death upon him” (Numbers Rabbah 19:10).
Moses had a special and unique relationship with God. On more than one occasion, the Torah describes Moses challenging God – but those were always during one-on-one conversations. When Moses chose to act disrespectfully publicly the way he acted privately, God could not allow it to go unaccounted.