ונפן ונסע המדברה THEN WE TURNED AND JOURNEYED INTO THE WILDERNESS — If they had not sinned, they would have passed by the way of Mount Seir to enter the Land from its south to its north, but because they became degenerate they had to turn towards the wilderness which is between the Red Sea and the south of Mount Seir, and they proceeded along its southern side from the west to the east, דרך ים סוף BY THE ROUTE FROM THE RED SEA — i.e. by the route which they had taken on leaving Egypt which is at the south-west corner. From there (where they were at that moment) they went towards the east.

ונסב את הר שעיר AND WE COMPASSED MOUNT SEIR, the whole of the south side as far as the land of Moab.

פנו לכם צפנה TURN YOU NORTHWARD — Turn you along the eastern side of Moab, from the south to the north, your faces directed to the north. Consequently they were travelling along the east side of Moab, and this is what is meant by (Judges 11:18) “And they came by the east side of the land of Moab”.

ונשמרתם מאד TAKE YE GOOD HEED TO YOURSELVES — And what is this "taking heed”? What follows: אל תתגרו בם CONTEND NOT WITH THEM.

עד מדרך כף רגל — This means, Even מדרך כף רגל, as much as to say: even only treading with the feet (a single step). The text means, I do not permit you to pass into their land without their permission. — A Midrashic explanation is: I shall not give you of their land until there come the day of the treading of the sole of foot upon the Mount of Olives (the Messianic period), as it is said, (Zechariah 14:4) "And his feet shall stand [in that day upon the Mount of Olives etc.]”.

ירשה לעשו [I HAVE GIVEN MOUNT SEIR] TO ESAU AS AN INHERITANCE from Abraham. The territory of ten clans I gave (promised) him (Abraham); seven of them will be yours (the seven clans of Canaan), and the Kenites, the Kenizzites and the Kadmonites, — who are Ammon, Moab and Seir — one of them already belongs to Esau, and the other two to the children of Lot (cf. Genesis Rabbah 44:23; and Rashi on Genesis 15:19); as a reward because he (Lot) went with him (Abraham) To Egypt, and kept silent about what he said regarding his wife, “She is my sister”, he treated him as his son (and therefore he, through his children Amon and Moab, inherited part of the land promised to him) (cf. Rashi on Genesis 19:29 and Genesis Rabbah 51:6).

תכרו — This is an expression denoting purchase. Similar is (Genesis 50:5; see Rashi thereon), “which I have bought (כריתי) for myself”, for thus in the coast cities do they use for "trading” the term כירה (Rosh Hashanah 26a).

כי ה' אלהיך ברכך FOR THE LORD THY GOD HATH BLESSED THEE — therefore you should not show yourselves ungrateful to Him by behaving as though you were poor, but act as rich people.

ונפן ונעבר AND WE TURNED AND PASSED, towards the north; we turned our faces to proceed along the eastern side (see Rashi on v. 3).

ואל תתגר בם וגו׳ AND DO NOT CONTEND WITH THEM [IN WAR] — As regards Moab He forbade them (the Israelites) only war against them, but they may frighten them, appearing before them when equipped for war; therefore it is written, (Numbers 22:3) "And Moab was afraid because of the people", because they took plunder and loot from them. But about the children of Ammon it is said, (v. 19) “Do not contend with them" — no provocation of any kind, — as a reward for the modesty shown by their ancestress, Lot's younger daughter, who did not publicly divulge regarding her father's conduct, as his elder daughter did, who called her son's name “Moab" (i.e. born of the father) (Bava Kamma 38b; see Rashi on Genesis 19:37).

ער is the name of the district.

האמים לפנים וגו׳ THE EMIM [ABODE THERE] FORMERLY — You might think that this is the land of the Rephaim which I gave (promised) to Abraham (Genesis 15:20), because the Emim who are Rephaim, dwelt there formerly (and they are one of the seven clans whose land you were to possess), but this is not that land, because those Rephaim I drove out from before the children of Lot and settled these in their stead (cf. Rashi on 3:13).

רפאים יחשבו וגו׳ THEY [ALSO] ARE ACCOUNTED REPHAIM, [AS THE ANAKIM] — As Rephaim are those Emim accounted, even as the Anakim — who are also termed Rephaim because the hands of everyone who beheld them became weak (רפה) (cf. Genesis Rabbah 26:7).

אמים — so called because the dread (אימה) of them lay upon the people. — So, too, (v. 12) the Horim dwelt formerly in Seir and I gave them over unto the children of Esau. (Genesis Rabbah 26:7)

יירשום — This is a present tense form of the verb; it is as much as to say, I gave them power that they might go on driving them out continuously.

היתה בם [FOR INDEED THE HAND OF THE LORD] WAS AGAINST THEM [TO DESTROY THEM] speedily within a period of forty years, so that they should no longer be the cause for their children to tarry in the wilderness.

ויהי כאשר תמו וגו׳ וידבר ה' אלי וגו׳ SO IT CAME TO PASS WHEN [ALL THE MEN OF WAR] HAD COME TO AN END … THAT THE LORD SPOKE TO ME etc. — But from when the spies were sent forth until now, the word וידבר is not mentioned in this section, but ויאמר, to teach you that during these entire thirty eight years during which the Israelites were lying under God’s censure, the Divine speech was not directed towards him in an expression of affection, face to face, and with tranquility of mind — to teach you that the Shechinah rests upon the prophets only for Israel’s sake (Sifra, Vayikra Dibbura d'Nedavah, Chapter 2 13; Mekhilta; cf. Rashi on Leviticus 1:1 towards end).

אנשי המלחמה THE MEN OF WAR — men from twenty years old and upwards, who went to war (cf. Numbers 14:29 and Rashi thereon).

אתה עבר היום את גבול מואב … וקרבת מול בני עמון THOU ART TO PASS THIS DAY THE BOUNDARY OF MOAB … AND THOU WILT APPROACH OPPOSITE THE CHILDREN OF AMMON — from here we see that the land of Ammon was on the north [of Moab].

ארץ רפאים תחשב IT (AMMON) ALSO WAS ACCOUNTED A LAND OF REPHAIM. — It also is accounted a land of Rephaim because the Rephaim formerly dwelt in it, but yet it is not that land which I gave to Abraham.

והעוים הישבים בחצרים וגו׳ BUT THE AVIM WHO DWELL IN HAZERIM etc. —The Avim are part of the Philistine people, for they are enumerated together with them in the Book of Joshua (Joshua 13:3), as it is said, “The five lords of the Philistines, the Gazathites, and the Ashdothites, and the Eshkalonites, the Gittites, and the Ekronites; also the Avim”. But because of the oath which Abraham had sworn to Abimelech, king of the Philistines (Genesis 21:24), Israel would have been unable to take their land out of their possession; but, says God, I brought the Caphtorites against them and they destroyed them and dwelt in their stead, and now you are permitted to take it (that land) from their (the Caphtorites) possession (Chullin 60b).

תחת כל השמים [THIS DAY I BEGIN TO PUT THE DREAD OF THEE … UPON THE NATIONS THAT ARE] UNDER THE WHOLE HEAVEN — This (the statement that the nations under the entire heaven will dread the Israelites) teaches that the sun stood still for Moses on the day of the battle with Og, and the matter was consequently known under the whole heaven (Avodah Zarah 25a).

ממדבר קדמות [AND I SENT MESSENGERS] FROM THE WILDERNESS OF KEDEMOTH — Although the Omnipresent had not commanded me to proclaim peace unto Sihon I learnt to do so from what happened in the wilderness of Sinai, i.e. from an incident that relates to the Torah which pre-existed (קדמה) the world. For when the Holy One, blessed be He, was about to give it (the Torah) to Israel, he took it round to Esau and Ishmael. It was manifest before Him that they would not accept it, but yet He opened unto them with peace. Similarly I first approached Sihon with words of peace. — Another explanation of ממדבר קדמות: Moses said to God, "I learnt this from what Thou didst say in the wilderness — from Thee Who wast in existence before (קדמת) the world. Thou couldst have sent one flash of lightning to bum up the Egyptians, but Thou didst send me from the wilderness to Pharaoh, to say gently, (Exodus 5:1) "Let my people go” (Yalkut Shimoni on Torah 764:27).

כאשר עשו לי בגי עשו AS THE CHILDREN OF ESAU DID TO ME — This does not refer to passing through their land (רק אעברה ברגלי) for Edom refused this, (cf. Numbers 20:18) but to the matter of selling food and water (also mentioned in the preceding verse).

עד אשר אעבר את הירדן UNTIL I SHALL PASS OVER THE JORDAN — This is to be connected with "Let me pass through thy land” (v. 27).

החלתי תת לפניך I HAVE BEGUN TO GIVE [SIHON] BEFORE THEE — He cast down the tutelary angel of the Amorites, who was in the upper spheres, beneath Moses’ feet and made him tread upon his neck (cf. Rashi on Numbers 24:2).

ויצא סיחן AND SIHON WENT FORTH — He did not send for Og to help him: this serves to teach you that they did not require one another's help, so mighty was each of them.

ואת בנו [AND WE SMOTE HIM] AND HIS SONS — It is written בנו, "his son" (although read as בניו "his sons"), for he had a son who was as mighty as himself (Midrash Tanchuma, Chukat 25).

מתם means MEN. — Of the spoil taken from Sihon it is stated (v. 35) בזזנו לנו, an expression denoting plunder (בזה), because then this was an object of desire to them, so that each man took spoil for himself. But when they came to the plundering of Og, they were already full to satiety, and it was contemptible in their eyes, so that they tore in pieces and cast away cattle and garments, and took only silver and gold. On this account it is said (Deuteronomy 3:7) בַּזֹּנוּ לנו which is an expression denoting "holding in contempt" (בזיון). Thus is it expounded in Siphre in the chapter beginning with "And Israel dwelt in Shittim״ (Numbers 25:1).

כל יד נחל יבק means, ALL THE DISTRICT BESIDE THE BROOK OF JABBOK.

וכל אשר צוה ה' אלהינו לנו — This means, AND ALL WHICH THE LORD OUR GOD COMMANDED US not to capture, we left.