Although the bulk of the parsha is about Eliezer finding a wife for Yitzchok, it ends by telling us where the descendants of Yishmael lived, מחוילה עד שור אשר על פני מצרים באכה אשורה (Bereishis 25:18). Assyria/אשור doesn’t seem to fit, as it’s very far away from שור and מצרים. Before trying to figure out the distance issue, let’s look at the location—and context—of the four places mentioned.
מצרים is Egypt, which we know is on the northeastern corner of Africa. שור is south of ארץ ישראל, parallel to קדש (see Bereishis 20:1), and although it’s unclear exactly where קדש is, or how many there were, it was definitely east of גרר, so שור is west. Which is why it’s “על פני מצרים” (facing Egypt), between Egypt and Israel. [This is one of the ways we know קריעת ים סוף was through the Gulf of Suez, as afterwards we entered מדבר שור (Shemos 15:22).] אשור was located on the Tigris River, in what is now northern Iraq.
חוילה was previously mentioned three times in Bereishis: it is a marker for one of the four rivers that came out of Gan Eden (2:11); חוילה is one of the sons of Kush (10:7), making him a grandson of Cham; and חוילה is one of the sons of Yuktun (10:29), making him a great-great-great-grandson of Shem. The חוילה near Gan Eden is Shem’s (see Ramban and Bechor Shor), and אשור is on one of the other four rivers, but since שור is near מצרים, and another of Cham’s sons, this חוילה could be either.
The Cham-based חוילה would be south of Kush; if this was the חוילה where the בני ישמעאל lived, they “fell” from the eastern part of central Africa, up the African coast through Egypt to שור, then all the way east (and north) to אשור. That’s a lot of ground to cover, and we have no (other) indication that ישמעאל extended into Africa. More importantly, since ישמעאל “fell” על פני כל אחיו (Bereishis 25:18; also see 16:12), i.e. near the sons of Keturah (and Yitzchok)—and they were not in Africa—this חוילה is disqualified.
The Shem-based חוילה was likely in the northern part of the Arabian Peninsula, since Yuktun’s other sons settled in Arabia. Additionally, Shaul smote Amalek “מחוילה בואך שור אשר על פני מצרים” (Shmuel I 15:7), and Amalek lived south of ארץ ישראל, so this חוילה must be just east of הר שעיר. If it was much farther east, between שור and חוילה would be more distant than between חוילה and אשור, with אשור north of חוילה. Besides, the order is backwards. Shouldn’t the פסוק have said “from שור to חוילה” (i.e. west to east →) before mentioning אשור, which is north (↑) of חוילה, rather than “from חוילה to שור”? Why go east to west (←) and then northeast (↑ )? Did the בני ישמעאל take over all the land within that triangle? Did they “fall” on two distinct lines starting from שור, one going east to חוילה and the other going northeast to אשור?
Keturah’s sons were sent “to the east” (25:6), which likely meant either northern Arabia or the eastern part of Jordan/Syria (or both). Either way, it’s not near אשור, and ישמעאל “fell” in front of them. Therefore, including “באכה אשורה” in the description seems problematic.
Because אשור is so far away, some (e.g. הכתב והקבלה) suggest that there must have been a different אשור much closer. Atlas Daat Mikra, discussing Keturah’s great-grandson אשורם (25:3), suggests that this was the אשור that joined our enemies (Tehillim 83:9) and the אשורי that איש בשת ruled over (Shmuel II 2:9). However, the traditional commentators understand the אשור in Tehillim to be the Assyrian kingdom, and the אשורי that איש בשת ruled over to be the Tribe of Asher. Besides, it would be very strange for the Torah to use אשור as a location reference if it didn’t mean the well-known אשור.
The Daat Mikra Bible Atlas explains our verse this way: “The Bible does not cite any particular country named for Ishmael, because all of his descendants are among the ‘tent dwellers’ (Judges 8:11) who lived as nomads in the vast deserts east of Eretz Yisrael, stretching as far as the Euphrates (the land of the Kedemites, the Syrian Desert), and south of it, toward Egypt and the Arabian Peninsula: ‘They camped from Havilah to Shur, which is east of Egypt, all the way to Ashur.’” I appreciate how they obfuscated the issue of the order of the place-names by making it seem as if “east of Egypt” refers to both Havilah and Shur (and translating “facing” as “east of”), but I don’t think that’s what the Torah meant. And although the Euphrates is relatively close to the Tigris, at אשור they’re not really that close.
In my opinion, the key is the word “באכה.” Does it mean “when you arrive at” the location referenced, or “as you approach” (i.e. in the direction of) the location mentioned? If it’s the latter, the distance from חוילה to אשור isn’t as big of an issue. It would be like traveling east on Route 4 in North Jersey; the signs will say New York, even if your destination is west of the Hudson River (or past New York City). Traveling west on I-80 is still towards the Delaware Water Gap whether you are going to Parsippany or Cleveland. Nevertheless, the distance is a bit curious, and the place-names seem out of order.
Nomads do not have a permanent home. They travel from place to place based on where they can pasture their flocks. As the בני ישמעאל multiplied, there were no cities to build up or expand. Instead, they had to spread out. It was this spreading that the Torah is trying to convey. Their tents stretched from חוילה to שור, but kept expanding eastward and northward. Which direction were they spreading? In the direction of אשור. Not that they reached that far, but were heading in that direction, with no definitive end point. By switching the order of the place names, the Torah is telling us that they originally “fell” from חוילה to שור, giving us the locations east to west before telling us the direction of their expansion, towards the east and the north.
Rabbi Dov Kramer looks forward to the fulfillment of the Yalkut Shimoni’s explanation of ישמעאל’s name (45): “Why was he called ישמעאל? Because in the future G-d will listen to the cries of the nation from what the בני ישמעאל do to them in the end-days.” May He answer our cries soon.