In the 40th year after leaving Egypt, towards the end of his life, Moshe gathered the nation together and rebuked them, alluding to the many places where they made mistakes since leaving Egypt. Moshe recalled the time spent at Mount Sinai after receiving the Torah, and that the nation could have gone from Sinai straight into the Land of Cana’an. At that stage, Moshe realised that he needed assistance to lead such a big nation.
Moshe therefore told the people to appoint judges over sub-groups of 1000, 100, 50 and 10 men. He told those judges to be fair and brave in their work, and that any dispute too difficult to resolve should be brought to Moshe himself.
Moshe recalled the sin of the spies. The people had approached Moshe 38 years earlier, wanting to send a mission to inspect the Land. Moshe agreed and selected 12 leading men, one from each tribe. Upon their return, Yehoshua and Calev spoke positively, but the other spies persuaded the people that going into the Land was impossible, due to the giants and strongly fortified cities. Moshe’s attempts to reassure the people of God’s protection when they would enter the Land were rejected. God then decreed that the generation who had accepted the negative report of the ten spies would die in the wilderness and not enter the Land.
Those aged under 20 at the time of the sin of the spies were allowed to enter the Land. Despite Moshe’s discouragement, some of the older people then attempted to enter the Land, despite Moshe’s warning that God would not now allow them to enter. They refused to listen and were brutally crushed by the Emorites. The nation wept and then turned back towards the Sea of Reeds.
Moshe then recalled that 38 years later, the Israelites turned northwards and passed by the descendants of Esav in Seir, making sure not to start a war with them, nor to take any provisions without payment. The nation then headed towards the Moabite desert. God instructed Moshe not to start a conflict with Moab. Conversely, on their march towards the Land, God instructed them to pass through the land of Sichon, the king of Cheshbon, even though this might lead to a war.
Sichon did come out to wage war. The Israelites destroyed him and his nation, taking his entire land, with the exception of Ammon. The nation then successfully defeated the other Emorite king, the mighty Og, king of Bashan, conquering his territory.
Moshe apportioned the land taken from Sichon and Og to the tribes of Gad and Reuven and some of the tribe of Menashe (as detailed in parashat Matot – see Bemidbar 32). However, the men of these tribes were still required to enter the Land of Cana’an to fight with the rest of the nation. Moshe told his successor Yehoshua that just as God had helped them to defeat Sichon and Og, so too He would help them in their conquest of the Land.