The parashah recounts how Moses appointed chiefs, the episode of the Twelve Spies, encounters with the Edomites and Ammonites, the conquest of Sihon and Og, and the assignment of land to the tribes of Reuben, Gad, and Manasseh.
[2] The first reading tells how, in the 40th year after the Exodus from Egypt, Moses addressed the Israelites on the east side of the Jordan River, recounting the instructions that God had given them.
[3] When the Israelites were at Horeb—Mount Sinai—God told them that they had stayed there long enough, and it was time for them to make their way to the hill country of Canaan to take possession of the land that God swore to assign to their ancestors, Abraham, Isaac, and Jacob, and their heirs after them.
[4] Then Moses told the Israelites that he could not bear the burden of their bickering alone, and thus directed them to pick leaders from each tribe who were wise, discerning, and experienced.
[14] But the Israelites flouted God's command and refused to go into the land, instead sulking in their tents about reports of people stronger and taller than they and large cities with sky-high walls.
[31] The Israelites spent 38 years traveling from Kadesh-barnea until they crossed the wadi Zered, and the whole generation of warriors perished from the camp, as God had sworn.
[34] God instructed the Israelites to set out across the wadi Arnon, to attack Sihon the Amorite, king of Heshbon, and begin to occupy his land.
[45] In the seventh reading, Moses defined the borders of the settlement east of the Jordan, and charged the Reubenites, the Gadites, and the half-tribe of Manasseh that even though they had already received their land, they needed to serve as shock-troops at the head of their Israelite kinsmen, leaving only their wives, children, and livestock in the towns that Moses had assigned to them until God had granted the Israelites their land west of the Jordan.
[52] Dennis Pardee suggested that the Rephaim cited in Deuteronomy 2:11, 20; 3:11, 13 (as well as Genesis 14:5; 15:20) may be related to a name in a 14th century BCE Ugaritic text.
Deuteronomy 1:1 begins: "These are the words that Moses spoke to all Israel on this side of the Jordan in the wilderness, in the plain opposite Suph, between Paran, Tophel, Laban, Hazeroth, and Dizahab."
[59] The Avot of Rabbi Natan read the listing of places in Deuteronomy 1:1 to allude to how God tested the Israelites with ten trials in the Wilderness, and they failed them all.
"[60] Similarly, the school of Rabbi Yannai interpreted the place name Di-zahab (דִי זָהָב) in Deuteronomy 1:1 to refer to one of the Israelites' sins that Moses recounted in the opening of his address.
Rabbi Hiyya bar Abba likened it to the case of a man who had a son and bathed him, anointed him, gave him plenty to eat and drink, hung a purse round his neck, and set him down at the door of a brothel.
Rabbi Samuel bar Naḥmani thus concluded that a woman who solicits her husband to perform the marital obligation, as Leah did, will have children the like of whom did not exist even in the generation of Moses.
[71] Interpreting Deuteronomy 1:15, the Rabbis taught in a baraita that since the nation numbered about 600,000 men, the chiefs of thousands amounted to 600; those of hundreds, 6,000; those of fifties, 12,000; and those of tens, 60,000.
Rabbi Judah interpreted the words "between your brethren" in Deuteronomy 1:16 to teach judges to make a scrupulous division of liability between the lower and the upper parts of a house, and Rabbi Judah interpreted the words "and the stranger that is with him" in Deuteronomy 1:16 to teach judges to make a scrupulous division of liability even between a stove and an oven.
[80] Rabbi Ammi cited the spies' statement in Deuteronomy 1:28 that the Canaanite cities were "great and fortified up to heaven" to show that the Torah sometimes exaggerated.
"[82] The Mishnah taught that it was on Tisha B'Av (just before which Jews read parashah Devarim) that God issued the decree reported in Deuteronomy 1:35–36 that the generation of the spies would not enter the Promised Land.
Rav Hiyya bar Abin thus argued that the words, "I have given Ar to the children of Lot as a heritage," in Deuteronomy 2:9 establish gentiles' right to inherit.
[87] Reading Deuteronomy 2:9, "And the Lord spoke to me, ‘Distress not the Moabites, neither contend with them in battle,'" Ulla argued that it certainly could not have entered the mind of Moses to wage war without God's authorization.
Interpreting the words, "Who dwelt at Heshbon," the midrash taught that had Sihon and his armies remained in different towns, the Israelites would have worn themselves out conquering them all.
The midrash taught that Moses was afraid, as he thought that perhaps the Israelites had committed a trespass in the war against Sihon, or had soiled themselves by the commission of some transgression.
"[101] The parashah is discussed in these medieval Jewish sources:[102] Maimonides taught that Deuteronomy 1:2 notes that "it is eleven days from Horeb to Kadesh-barnea by the Mount Seir route" to attest to how miraculous it was that the Israelites remained in the wilderness for 40 years, with a daily supply of manna.
Maimonides read Exodus 18:21, "men of power," to refer to people who are mighty in their observance of the commandments, who are very demanding of themselves, and who overcome their evil inclination until they possess no unfavorable qualities, no trace of an unpleasant reputation, even during their early adulthood, they were spoken of highly.
Thus Maimonides taught that one violates a negative commandment when one appoints a judge who is not fitting or is not learned in the wisdom of the Torah and is not suitable to be a judge—even if the appointee is entirely a delight and possesses other positive qualities.
[107] Maimonides cited the report of Deuteronomy 1:28, "cities walled and fortified, rising up to heaven," as an instance of how Scripture sometimes uses hyperbolic or exaggerated language.
[108] Reading God's instruction in Deuteronomy 2:6 that the Israelites should buy food, Abraham ibn Ezra commented that this would be only if the Edomites wanted to sell.
Ibn Ezra noted that some view Deuteronomy 2:6 as asking a question, for Israel had no need for food and drink (having had manna daily).
Excavations at Tel Hesban south of Amman, the location of ancient Heshbon, showed that there was no Late Bronze Age city, not even a small village, there.
And Finkelstein and Silberman noted that according to the Bible, when the children of Israel moved along the Transjordanian plateau they met and confronted resistance not only in Moab but also from the full-fledged states of Edom and Ammon.