“Behold I am sending a messenger before you” (Sh’mos 23:20). Rashi explains this “messenger” to be the angel who would have been sent to lead the nation after the sin of the golden calf had Moshe not pleaded with G-d that He should still lead the nation Himself (Sh’mos 33:15-16 and 34:9). This angel eventually did lead the nation, after Yehoshua took over the leadership (see Ramban on 33:21).

Rashi’s explanation raises several issues, including why G-d would mention the angel He wanted to send after they sinned if at this point they hadn’t sinned yet, and why Moshe didn’t protest (this first time) when he was told that G-d didn’t plan on leading the nation Himself.

Another issue it raises is based on the borders that G-d set (here) for the Land of Israel, “from the Sea of Reeds until the Sea of the P’lishtim and from the desert until the river” (Sh’mos 23:31). One of these boundaries is the Sea of Reeds (Yam Suf, or Red Sea), the sea that, immediately after the exodus from Egypt, G-d had miraculously split in order to allow the nation to cross before drowning their former oppressors in it. As this sea surrounds the Sinai Peninsula on three sides, it was the western part that they crossed (into the Sinai Peninsula from Egypt), and the eastern part that (according to most) is referred to here as the eastern border of Israel. However, when the boundaries are described prior to the nation entering the land (Bamidbar 34:3), the southeastern corner is the bottom of the Dead Sea, which is much further north than Etzyon Gever (modern day Eilat), by the Gulf of Aqaba (the northern point of the eastern leg of the Red Sea). Why is the border here given as the Sea of Reeds rather than the Dead Sea? Besides, the border never actually reached that far south. Even at Israel’s height (during the reign of King Solomon), the nation that lived at Etzyon Gever feared the Kingdom of Israel, and therefore sent it gifts, as well as following whatever it was asked or told to do (see M’lachim I 8:26-28), but was not actually part of the Land of Israel. [It should be noted that when the nation went from the Sinai Peninsula to “the other side of the Jordan” (when they passed by Edom and Moav before conquering the land on the eastern side of the Jordan from Sichon and Og) they had to travel between the bottom of the Dead Sea and the top of the eastern leg of the Red Sea, which is north of Etzyon Gever (see Bamidbar 33:35-36). According to the boundaries given here, they passed through part of the Promised Land!]

It would also be difficult to ascribe this boundary to any time other than Moshe’s, as the verses immediately prior to this are describing the initial conquest of the land. We are even told that they didn’t conquer it in its entirety because it was too vast for the size of the nation at the time, with these borders being given in order to show just how vast the Land of Israel was (see Ibn Ezra and Malbim). If the nation never conquered enough land to make the Yam Suf its boundary, why is it mentioned here with the other boundaries?

Many commentaries (i.e. Ibn Ezra, Ralbag, Radak, Metzudas Dovid and Rashi) equate the boundaries listed here with those in Tehillim 72:8 (“and he had dominion from sea to sea and from the river to the edge of land”) and/or to Zecharya 9:11 (“and he ruled from sea to sea and from the river to the edge of land”). The Ibn Ezra, Radak and Metzudas Dovid say the former can apply either to King Solomon (which is why he only “has dominion” but doesn’t “rule”) or to Moshiach, while the latter applies to Moshiach. The question is therefore not why the Yam Suf is given as a boundary at all, but why is it given as a boundary in our Parasha, speaking to the nation that had just come out of Egypt and would (have) shortly start(ed) conquering the land. Similarly, the “river” mentioned as the fourth boundary is the Euphrates, which also wasn’t conquered during the initial conquest and usually refers to what the boundaries will eventually be. Why were two boundaries mentioned here that were not relevant to Moshe or Yehoshua?

Rabbeinu Avraham ben HaRambam says that the boundaries given here are those implied in the words “And when G-d will widen your boundaries as he swore to your fathers, and He gives you all of the land that He spoke of giving your fathers” (D’varim 19:8; the second “fathers” referred to here might be the generation that came out of Egypt, while the first “fathers” refers to the Patriarchs). This is how Midrash Lekach Tov and Midrash Aggadah explain the boundaries given in our Parasha, as does the Mechilta (Bo 12). Why were these future boundaries given here? It would seem that since the sin of the golden calf (and of the spies) hadn’t yet occurred, these would have been the actual borders had they entered now; it was only after they sinned that the borders were scaled back, to be expanded in the future.

Which brings us to the additional issue with Rashi’s explanation of the “angel” G-d referred to; How could G-d tell them how the nation will be led after they sin (by an angel) if just a few verses later He sets the boundaries of the land they will be led to (by this angel) based on them not sinning? Was G-d telling the nation what things will be like because they are going to sin, or how they would have been if they didn’t?

Rambam (Moreh Nevuchim 2:34), as well as Ralbag, Rosh, Bechor Shor and Midrash HaGadol (in our Parasha), understand the “messenger” G-d will send to lead the nation to the Promised Land to be a prophet (i.e. Moshe and then Yehoshua). Vayikra Rabbah (1:1) quotes numerous verses where a prophet is referred to as G-d’s “messenger.” Sh’mos Rabbah (32:2) says that G-d’s was presenting the nation with a choice; “if you merit it, I (G-d) Myself will lead you,” but if not, “I will give you over to a messenger.” It can therefore be suggested that the word “messenger” in our verse has a dual meaning (see page 5 of www.aishdas.org/ta/5764/mishpatim.pdf for another example of a possible dual meaning in our Parasha); if you don’t sin, the “messenger” referred to will mean a prophet (Moshe, who will take directions directly from G-d), but if you do sin, it will mean an angel (placing an additional layer between G-d and the nation). Alternatively, it could refer to an angel who is a messenger (such as Micha’el) or the angel who speaks directly for G-d (“Matatron,” see Rambam on Sh’mos 12:12 and 23:21), depending on whether or not we sin. Either way, G-d was telling them that there is more than one possibility as to how the nation will be led, depending on their behavior.

After laying out all of the laws in Parashas Mishpatim, G-d told the nation that the way He will relate to them depends on how they relate to Him; it could be a more direct relationship or a less direct relationship. If they fulfill the mitzvos properly, it will be a more direct relationship, including inheriting a larger amount of land (with wider boundaries). Moshe didn’t protest (yet) because G-d wasn’t saying that He will definitely send an angel instead of Him, but that it was a possibility. Unfortunately, that possibility became a reality, at which point Moshe did protest. And even though Moshe was abe to delay the advent of the nation being led by the angel, we are still awaiting the time when the boundaries will be expanded to match those G-d described here.