The following was written in Hebrew by Rav Eliyahu Shlesinger in his book אלה הדברים. I'll try my best to translate it.
אֵלֶּה הֵם בְּנֵי יִשְׁמָעֵאל, וְאֵלֶּה שְׁמֹתָם, בְּחַצְרֵיהֶם, וּבְטִירֹתָם--שְׁנֵים-עָשָׂר נְשִׂיאִם, לְאֻמֹּתָםThese are the sons of Ishmael, and these are their names, by their courtyards, and by their encampments; twelve princes according to their nations. (Bereishit 25:16)
בְּחַצְרֵיהֶם "by their villages" - cities that have no wall. And the Targum says בפצחיהון since they are open, an expression of opening, just as יפצחו ורננו (Rashi)
I saw a deep idea of Rav Yitzhak Hutner ZT"L that is fitting to publicize.
In the calculation of the families of Yishmael, we find an expression of "נְשִׂיאִם לְאֻמֹּתָם - princes according to their nations", whereas by Eisav, it has an expression of "chiefs" - "אלופי עשו - chiefs of Eisav" (Bereishit 36:15
) The difference between them extends throughout every stage of history, and serves as a source and root for the difference between Yishmael's relations with the Jewish people and those of Eisav. The explanation is according to what Haza"l set up as the definition of "Aluf - chief" as מלכותא בלא תגא - a king without a crown (Sanhedrin 99b
). Eisav really merited kingship "ולאום מלאום יאמץ - and the one people shall be stronger than the other people" (Bereishit 25:23
). However, his kingship is limited, and will only continue until the period of "ועלו מושיעים בהר ציון לשפוט את הר עשו - And saviours shall come up on mount Zion to judge the mount of Esau" (Ovadia 1:21
The crown really belongs to Yaakov. However, Yishmael only has princes - an expression of honor and greatness, but without the power of kingship.
This is the difference between Yishmael and Eisav: Eisav is an actual inheritor. "וָאֶתֵּן לְעֵשָׂו אֶת-הַר שֵׂעִיר, לָרֶשֶׁת אוֹתוֹ - and I gave unto Esau mount Seir, to possess it" (Yehoshua 24:4
) " כִּי-יְרֻשָּׁה לְעֵשָׂו, נָתַתִּי אֶת-הַר שֵׂעִיר - because I have given mount Seir unto Esau for a possession" (Devarim 2:5
), whereas regarding Yishmael, it says the opposite: "גָּרֵשׁ הָאָמָה הַזֹּאת, וְאֶת-בְּנָהּ: כִּי לֹא יִירַשׁ בֶּן-הָאָמָה הַזֹּאת - Cast out this bondwoman and her son; for the son of this bondwoman shall not be heir" (Bereishit 21:10
). Eisav, as the role of an inheritor, gets the power of inheritance - with a specific limitation - from our forefathers. Anyone who has a listening ear to the tones of Scripture will be able to distinguish with the minutest difference between what was said by the calculation of the lineage of the chiefs of Eisav "אֵלֶּה אַלּוּפֵי אֱדוֹם, לְמֹשְׁבֹתָם בְּאֶרֶץ אֲחֻזָּתָם - These are the chiefs of Edom, according to their habitations in the land of their possession" (Bereishit 36:43
) and what was said regarding the princes of Yishmael "וְאֵלֶּה שְׁמֹתָם, בְּחַצְרֵיהֶם, וּבְטִירֹתָם - and these are their names, by their courtyards, and by their encampments" (Bereishit 25:16
What kind of term of identification of the dwelling-place of the princes of Yishmael is בחצריהם - in their courtyards?!?! However, that's exactly the point! Eisav is an inheritor, and he has his own dwelling and his own place. However, Yishmael is not an inheritor and does not have his own place. Regarding this, it says "בְּחַצְרֵיהֶם, וּבְטִירֹתָם - by their courtyards, and by their encampments", which are more temporary concepts than a dwelling-place and inheritance.
Eisav, who is his own inheritor and got his inheritance, cannot go and claim [Eretz Yisrael] as a portion of his inheritance. However, Yishmael comes with his full jealousy and anger over Eretz Yisrael: "It's mine". And this is the rage of someone who does not have an inheritance, since he was excluded from an inheritance, and he's coming to take the portion of inheritance of the inheritor from his family member. And this is the foundation of all the murder and anger that we have seen with our own eyes in our days of the children of Yishmael over the inheritance in Eretz Yisrael...
These words were said [by Rav Hutner] in the year 5730. And how beautiful and enlightening they are for our own days.
And from one idea to another idea within the same idea - the inheritance of the land.
The first person that identified the irrational and non-understandable behavior of Yishmael was Sarah Imeinu, A"H, who, immediately after the birth of her son Yitzhak, saw the son of Hagar "מצחק - playing around".
Hazal said in Bereishit Rabba: "This is not an expression of fooling around, but rather, an expression of inheritance, since at the time that our father Yitzhak was born everyone was happy. Yishmael, however, told them: 'You are fools. I am the first-born and I get a double-portion.' Because you learn this from the answer that Sarah gave Avraham: 'for the son of this bondwoman shall not be heir with my son...' " We see that Yishmael in all generations believed with all his heart that he is the inheritor, that he deserves the land due to its spiritual blessings. And therefore, in all generations, Yishmael tries to kill Yitzhak, who is his greatest arch-enemy.
It's brought down in Midrash (Bereishit Rabba 52:15): "Yishmael said to Yitzhak: 'Let's go and see our portion in the field.' So Yishmael would take his bow and arrows and shoot toward Yitzhak, and pretend as if he's מצחק - playing around." Please look at what Yishmael said "Let's go and see our portion
". Already then, Yishmael is hiding knives in his pocket and is waiting for the right moment in order to attack and kill Yitzhak - because Yishmael has a general rule: "the ends justify the means". The ends are the land of Eretz Yisrael. The means are "ידו בכל - his hand is in everyone". And with his great hatred of Yitzhak, he doesn't loathe any means in order to reach the ends [of taking Eretz Yisrael from those] to whom it is an inheritance and belongs only to them. This hatred continuously gets stronger, and perhaps will never be extinguished. Ribbi Moshe Cordovero (on the Zohar, Parshat Vayeira) expressed this properly: "The children of Yishmael will in the future - at that time - awaken together with all the nations of the world to come to Yerushalayim... and all the nations will gather and make a peace treaty between them, and they will turn against Israel to destroy... and it will be a time of trouble for Yaakov. However, they will not come to break [us] - rather, from it, he will be saved."
How does this blood-battle end? And when will we merit that this land will quiet down for not just 40 years - but forever?
For this, the Torah concludes (Bereishit 25:8-9
)"וַיִּגְוַע וַיָּמָת אַבְרָהָם בְּשֵׂיבָה טוֹבָה וכו' וַיִּקְבְּרוּ אֹתוֹ יִצְחָק וְיִשְׁמָעֵאל, בָּנָיו, אֶל-מְעָרַת, הַמַּכְפֵּלָה - And Abraham expired, and died in a good old age...And Isaac and Ishmael his sons buried him in the cave of Machpelah." Rashi explains, quoting the Midrash, "From here we see, that Yishmael did Teshuva, and had Yitzhak go in front of him, and that is the 'good old age' that is said about Avraham." In other words, there will come a day that Yishmael will recognize his mistake and understand that the first-born rights go to Yitzhak, as even the Torah had Yitzhak first "וַיִּקְבְּרוּ אֹתוֹ יִצְחָק וְיִשְׁמָעֵאל, בָּנָיו - And Isaac and Ishmael his sons buried him." He will understand that Eretz Yisrael is given to the descendants of Yitzhak in order to concretize the Torah of Avraham Avinu A"H on its land. And this is how the long blood bath will end - Yishmael will do Teshuva.
And about the question we asked - when will this occur? We have no answers. The Rambam already wrote about the era of the days of Mashiah "For we will not know how it will be until it happens." Nevertheless, there is a hint to this at the end of the Perasha: "על פני כל אחיו נפל - over against all his brethren he did settle (or fall)" (Bereishit 25:18
). And the beginning of the next Perasha is "ואלה תולדות יצחק - And these are the generations of Isaac". Regarding the juxtaposition of these Parshiot, the Ba'al HaTurim says, "When Yishmael will fall at the End of Days, then the son of David - who comes from the generations of Yitzhak - will sprout." From here we see that Yishmael will do Teshuva, and this will occur after he falls, after his military might will be broken, and his empty pride will disappear, and then, we will merit "And the redeemer comes to Zion."