📜 Daily Chumash & Rashi – Parshas Devarim: Chamishi – Moshe recounts passing the borders of Eisav

Author: Rabbi Yaakov GoldsteinPublished: July 16, 2026

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*The article below is an excerpt from the above Sefer

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Chamishi

  • Moshe recounts passing the borders of Eisav: Hashem said to me that we have spent enough time circling the mountain and we should travel towards north. We were warned by Hashem that while traveling through the border of Eisav we are to take great heed not to instigate them, as we will not inherit even one parcel of their land. We shall buy food and water from them.
  • Moshe recounts passing the borders of Moav: So, we passed the border of Eisav and traveled towards the desert of Moav. Hashem warned us not to oppress Moav or instigate them into war, as their land will not be given to us as an inheritance. We were then instructed to travel across Nachal Zared. It took us 38 years to travel from Kadeish until crossing Nachal Zared, by which time the entire generation had already passed away.
  • Moshe recounts passing the borders of Ammon: Hashem told us that we will be passing the border of Moav and arrive by the nation of Ammon. Hashem warned us not to oppress or instigate them, as it will not be given to us as an inheritance.
  • Moshe recounts passing the border of Sichon: Hashem told us to go travel past Nachal Arnon and instigate a war with Sichon the Emorite king, as he will be handed into our hands. I sent envoys to Sichon with a peaceful message saying that we request to pass though his land, and we will go through the kings road and not swerve right or left. We will purchase food and drink from you, just as was done when we passed the land of Seir and Moav. However, Sichon refused our entry due to Hashem hardening his heart so he be handed over to us.

 

 

Q&A on Rashi

 

📘 Rashi Q&A — Devarim 2:2–30

2:2–3 — End of the Wandering Around Se’ir

Q1. What did Hashem tell Moshe after many years of circling Mount Se’ir?

  1. “You have circled this mountain long enough; turn northward.”

Q2. Which direction did Israel now travel?

  1. Along the eastern side of Edom, moving from south to north.

Q3. What verse does Rashi connect to this route?

  1. “They traveled to the east of Moab.”

 

2:4–5 — Edom’s Territory

Q4. What warning did Hashem give regarding Edom?

  1. Do not provoke them.

Q5. Why were Israel forbidden to attack Edom?

  1. Because Hashem gave Mount Se’ir to Esau as an inheritance.

Q6. What does “not even a footstep” mean?

  1. Israel could not even set foot there without permission.

Q7. What is Rashi’s Midrashic interpretation?

  1. It alludes to a future time when Hashem’s feet will stand on the Mount of Olives.

Q8. Why did Esau receive Se’ir?

  1. As part of Abraham’s promised inheritance.

 

2:5 — Lot’s Reward

Q9. Which territories were given to Lot’s descendants?

  1. Moab and Ammon.

Q10. Why were Lot’s descendants rewarded?

  1. Lot remained silent when Abraham called Sarah his sister in Egypt.

 

2:6–7 — Buying Food and Water

Q11. Were Israel allowed to take supplies for free?

  1. No, they had to buy food and water.

Q12. What does “תכרו” mean?

  1. To buy or purchase.

Q13. Why were they commanded to pay?

  1. Hashem had blessed them abundantly, so they should behave like wealthy people.

Q14. What had Hashem provided throughout the wilderness?

  1. Everything they needed; they lacked nothing.

 

2:8 — Passing Edom

Q15. What happened after leaving the descendants of Esau?

  1. Israel turned northward and traveled along Edom’s eastern side.

 

 

2:9 — Moab

Q16. What restriction applied to Moab?

  1. Israel could not provoke them into war.

Q17. Were Israel permitted to frighten Moab?

  1. Yes, they could appear armed and inspire fear.

Q18. What evidence shows Moab was frightened?

  1. “Moab became terrified because of the people.”

Q19. Why were the Ammonites given even greater protection?

  1. As a reward for the modesty of Lot’s younger daughter.

Q20. What is “Ar”?

  1. The name of the province of Moab.

 

2:10–12 — The Emim and Horites

Q21. Who were the Emim?

  1. A giant people who previously lived in Moab.

Q22. Why were they called Emim?

  1. They inspired fear (אֵימָה) in others.

Q23. Why were they considered Rephaim?

  1. Their appearance caused people’s strength to weaken from fear.

Q24. What happened to them?

  1. Hashem drove them out and gave the land to Lot’s descendants.

Q25. Who previously lived in Se’ir?

  1. The Horites.

Q26. What happened to them?

  1. Esau’s descendants dispossessed them and settled there.

Q27. What does “יירשום” mean?

  1. They gradually and continually drove them out.

 

2:13–15 — Crossing Zered

Q28. What marked the end of the condemned generation?

  1. Crossing the Zered Brook.

Q29. How many years passed from Kadesh Barnea until Zered?

  1. Thirty-eight years.

Q30. Why did Hashem hasten the deaths of the generation?

  1. So they would not delay their children from entering the Land.

 

2:16–19 — Renewed Divine Speech

Q31. What happened after the last of the condemned generation died?

  1. Hashem again spoke to Moshe with the expression “וידבר”.

Q32. Why is that significant?

  1. During the thirty-eight years of disfavor, Hashem did not speak to Moshe with the same intimate form of communication.

Q33. What does this teach about prophecy?

  1. The Divine Presence rests upon prophets because of Israel.

Q34. Who are “the men of war”?

  1. Men over twenty years old eligible for military service.

Q35. What geographical lesson does Rashi derive here?

  1. Ammon lay north of Moab.

Q36. What command was given concerning Ammon?

  1. Neither distress nor provoke them.

 

2:20–22 — The Zamzumim

Q37. Who were the Zamzumim?

  1. A giant people who previously occupied Ammon.

Q38. Were they part of Abraham’s promised inheritance?

  1. No.

Q39. What happened to them?

  1. Hashem destroyed them and gave their land to the Ammonites.

Q40. What parallel does Rashi draw?

  1. Just as Hashem gave Se’ir to Esau by removing the Horites.

 

2:23 — The Avim

Q41. Who were the Avim?

  1. A people associated with the Philistines.

Q42. Why couldn’t Israel originally conquer their territory?

  1. Because of Abraham’s oath to Avimelech.

Q43. How did Hashem solve this problem?

  1. The Kaftorim destroyed the Avim and settled there.

Q44. Why did this matter?

  1. Israel could now lawfully take the territory from the Kaftorim.

 

2:24–25 — Beginning the Conquest

Q45. What new command did Hashem give?

  1. Begin conquering Sichon and his territory.

Q46. What would Hashem place upon the nations?

  1. Fear and dread of Israel.

Q47. How does Rashi explain “under the entire heaven”?

  1. The miracle of the sun standing still for Moshe became known throughout the world.

 

2:26–29 — Moshe’s Peace Proposal

Q48. From where did Moshe send messengers to Sichon?

  1. From the Desert of Kedemot.

Q49. Why did Moshe first offer peace?

  1. He learned this from Hashem’s own conduct.

Q50. What example did Moshe learn from?

  1. Hashem offered the Torah to Esau and Yishmael before giving it to Israel.

Q51. What is Rashi’s second explanation?

  1. Moshe learned from Hashem’s dealings with Pharaoh, whom He first approached peacefully.

Q52. What did Moshe request from Sichon?

  1. Safe passage and the opportunity to buy food and water.

Q53. What does “just as the descendants of Esau did for me” mean?

  1. They sold Israel food and water.

 

2:30 — Sichon’s Refusal

Q54. Why did Sichon refuse?

  1. Hashem hardened his spirit and strengthened his heart.

Q55. Why did Hashem do this?

  1. In order to deliver Sichon and his land into Israel’s hands.
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