In the fortieth year since the Exodus, the Children of Israel approach the borders of the Promised Land, encountering all the surrounding nations. In the first of these confrontations, they find themselves on the outskirts of the territory of the descendants of Esav, the Edomites.

Moshe requests permission for safe passage:
And Moshe sent messengers from Kadesh (MALACHIM MIKADESH) to the king of Edom: “Thus said your brother Israel: You know all the travail that has befallen us. And our fathers descended to Egypt, and we dwelt in Egypt for many years, and the Egyptians dealt ill with us, and with our fathers. And we cried out to Hashem, and He heard our voice, and He sent a messenger (MALACH), and he took us out of Egypt. And behold we are in Kadesh, a city on the edge of your boundary. Let us please pass through your land; we will not pass through field or vineyard, nor shall we drink the water of the well. By the king’s road we will go — we will not veer right or left — until we have crossed your border.”
And Edom said to him: “You will not pass through me, lest with the sword will I come out towards you.”
And the Children of Israel said to him: “By the path will we ascend, and if we drink of your water, I or my livestock, then I shall give its value. Only, it is no matter, let me pass through on foot.”
And he said, “You will not pass through!” And Edom came out towards him with a massive army and with a strong hand. And Edom refused to allow Israel to cross his border. And Israel turned away from him
(Bamidbar 20:14-21).

We would like to explain this incident according to the Haamek Davar (R. Naftali Tzvi Yehudah Berlin, 1817-1893), who notices a few subtle peculiarities. First, it was unnecessary to mention that Moshe sent the messengers from Kadesh (possibly Petra, in Jordan). Shortly before this incident it says that “the nation dwelt in Kadesh” (20:1), and immediately after the encounter with Edom we are told that “they traveled from Kadesh” (20:22).

Second, the words messengers from Kadesh (MALACHIM MIKADESH) are in an unconventional order. Compare this with the spies sent by Yehoshua:
And Yehoshua bin-Nun sent from the Shittim two men as spies (MIN HASHITTIM SHNAYIM ANASHIM MERAGLIM) (Yehoshua 2:1).
There, the point of origin of the mission is mentioned before the agents.

Haamek Davar concludes that Moshe does not send Israelites, but rather local people, either Edomites or others, messengers from Kadesh, to the king of Edom. When a small number of Israelites are conspicuous among a large number of people from the nations, dangers can befall them. Witness what occurred in the days of David (Shmuel II, chapter 10): Nachash, king of the Ammonites died and David sent a deputation to comfort his son Chanun. But the Ammonite royal advisers suspect them of spying in preparation for conquest, and Chanun sends them back, but not before shaving off half their beards and cutting off half their garments. This results in a devastating war against Ammon and their allies the Arameans. To avoid this kind of humiliation, or worse, Moshe sends locals.

Furthermore, there is a distinction between the two delegations sent to Edom. The first time, Moshe sends them. However, the second time we read that “the Children of Israel said to him” — Why the difference?

After the splitting of the Sea of Reeds, the Children of Israel sang
Then will the captains of Edom be terrified (Shemot 15:15).
Haamek Davar explains that at first the Edomites were frightened of Israel. However, as a result of the sin of the spies the Israelites would have to circumnavigate the land of Edom, and this fear would dissipate, as we see now. Only “Then” — after the defeat of Sichon and Og (Bamidbar 21:21-35) — would Edom’s fear of Israel be restored.

It is important for Edom to remain afraid of Israel precisely because Israel would not conquer his territory until Messianic times (see Rashi on Bereishit 15:19). As Hashem had said to Moshe:
For I shall not give you of their land even the space of a footstep (Devarim 2:5).
The fear would keep them from harassing Israel.

But Hashem decreed that Edom attain that fear following an attitude of overconfidence:
And they will fear you, so you must take great care (ibid., verse 4).
Therefore, Moshe needed to determine Edom’s disposition first. If they were truly afraid, Israelite messengers would have taken note of Edom’s fear. Then Israel would have insisted on advancing through Edom. Moshe would have had to oppose the people’s will, because Hashem wanted Edom to lose its nerve, not to start off frightened. On the other hand, by sending locals — who would only deliver messages and ignore Edom’s morale — Moshe avoided this.

Moshe’s description of the Exodus downplays Divine intervention, so as not to frighten Edom prematurely:
And we cried out to Hashem, and He heard our voice, and He sent a messenger (MALACH), and he took us out of Egypt.
There is no mention of the Ten Plagues or the splitting of the Sea of Reeds. Moreover, Moshe expected Edom to mistake MALACH for the “guardian angel” that Israel, like every other nation, has. In reality, MALACH refers to Moshe himself, Hashem’s prophet. Without lying, Moshe allowed the king of Edom to deceive himself.

The king of Edom’s declaration
lest with the sword will I come out towards you
demonstrates Edom’s self-assuredness; the stage is set for it to lose its confidence, and Moshe does not need to send another message. The rest of Israel however, continues to try, until Edom blocks their entry. With the overthrow of Sichon and Og “will the captains of Edom be terrified.”

Albert Camus wrote:
“The spirit together with the sword will always win out over the sword alone.”