After what was Nachal Eshkol named?

Summary: After the cluster of grapes, but what about the Biblical character Eshkol? And why does it seem to be called that before they even arrived? The Gra has an interesting suggestion, which I then analyze. See also this earlier post, about dual etymology of Nachal Eshkol.

Post: In Shelach, there is a place called Nachal Eshkol.

23. They came to the Valley of Eshkol and they cut a branch with a cluster of grapes. They carried it on a pole between two [people] and [they also took] some pomegranates and figs.

כג. וַיָּבֹאוּ עַד נַחַל אֶשְׁכֹּל וַיִּכְרְתוּ מִשָּׁם זְמוֹרָה וְאֶשְׁכּוֹל עֲנָבִים אֶחָד וַיִּשָּׂאֻהוּ בַמּוֹט בִּשְׁנָיִם וּמִן הָרִמֹּנִים וּמִן הַתְּאֵנִים:

24. They called that place the Valley of Eshkol because of the cluster [eshkol] the children of Israel cut from there.

כד. לַמָּקוֹם הַהוּא קָרָא נַחַל אֶשְׁכּוֹל עַל אֹדוֹת הָאֶשְׁכּוֹל אֲשֶׁר כָּרְתוּ מִשָּׁם בְּנֵי יִשְׂרָאֵל:

But if the place name was due to this incident, and is assigned in pasuk 24, how can they have arrived at the place called Nachal Eshkol in pasuk 23?!

This is a question which is readily answered on a peshat level. They arrived at a place. That place was later to be known as Nachal Eshkol, for the reason given in pasuk 24, and so Moshe Rabbeinu referred to it initially by that name, giving the connection between the etymology and the incident in the very next pasuk.

Ibn Ezra says as much:
יג, כג]
עד נחל אשכול -דברי משה. 
ויתכן להיות כמו: וירדוף עד דן, להיות שם אחר.

As Mechokekei Yehuda explains it, when Ibn Ezra writes דברי משה, he means that Moshe Rabbenu wrote it at the end of the 40 years, at which point it already had this name. And his second explanation, about וירדוף עד דן, means that he called it that based on what would be future events, just as vayirdof ad Dan, when Dan had not yet been born. Or, regarding Dan that there were two names (places) called Dan. (Perhaps similarly, Eshkol didn't have a Nachal Eshkol, or if he did, it was a different place.) (There are are also different girsaot in this Ibn Ezra, which complicates matters.)

The Midrash Rabba also takes note of this, and gives its explanation:

לַמָּקוֹם הַהוּא, קָרָא נַחַל אֶשְׁכּוֹל, זה שאמר הכתוב, מַגִּיד מֵרֵאשִׁית אַחֲרִית, שהכל צפוי היה לפני הקדוש ברוך הוא. אשכול אוהבו של אברהם היה, ונקרא אשכול על אודות האשכול שעתידין ישראל לכרות ממקומו 

Eshkol was Avraham's friend, and it is called Eshkol because of the Eshkol that Israel was going to cut from its place in the future. The assumption appears to be, based on pasuk 23, that it was already called that, based on Avraham's friend, as well as future event. And thus, pasuk 24 states that it was called, in the past, Nachal Eshkol because of this future event which is now present. (See how the midrash reworks the pasuk, particularly towards the end.)

The Gra takes a similar tack, but takes it further. He writes as follows:
"And they came to Nachal Eshkol, etc... To that place he called Nachal Eshkol because of the Eshkol which the Bnei Yisrael cut from there. And there is to ask that is it not so that beforehand it was not called Nachal Eshkol? 23}? And so, how can it be said {in pasuk 23} that they came to Nachal Eshkol. And there is to clarify that, in truth, even initially it was called Nachal Eshkol, based on the name of a man who was called Eshkol, such as Aner, Eshkol and Mamre {Avraham's friends}. And behold, Eshkol, the name of the man, is chaser, without a vav. Therefore after the cutting of the cluster {eshkol} of grapes they called it Nachal Eshkol spelled plene with a vav, which connotes via this the plural, while a word which is chaser vav connotes singular. And that is why Chazal, in Masechet Sukkah (daf 6) cited "בסכת בסכת בסכות, behold there are here four," because baSukkat when chaseir connotes only one. And so too קרנת קרנת קרנות are four, for only the plene spelling connotes the plural. And it appears that there was a difference in pronunciation between a cholam malei and a cholam chaser. And so too here as well, one can say that initially the name of the place was called  {and pronounced} Nachal Eshkol chaser vav, as is written in the Torah, based on the man whose name was pronounced Eshkol {chaser}, and once they cut from there the Eshkol {malei} the place was called {and pronounced} Nachal Eshkol {malei} based on the name of the man Eshkol {chaser} and based on the Eshkol {malei} of grapes which they cut from there. Therefore it is written, 'and they came to Nachal Eshkol, chaser... to that place is called Nachal Eshkol, malei."

A few notes. Indeed, Eshkol the man is spelled chaser throughout. Thus:

בראשית פרק יד

• פסוק י"ג: וַיָּבֹא, הַפָּלִיט, וַיַּגֵּד, לְאַבְרָם הָעִבְרִי; וְהוּא שֹׁכֵן בְּאֵלֹנֵי מַמְרֵא הָאֱמֹרִי, אֲחִי אֶשְׁכֹּל וַאֲחִי עָנֵר, וְהֵם, בַּעֲלֵי בְרִית-אַבְרָם. 
• פסוק כ"ד: בִּלְעָדַי, רַק אֲשֶׁר אָכְלוּ הַנְּעָרִים, וְחֵלֶק הָאֲנָשִׁים, אֲשֶׁר הָלְכוּ אִתִּי:  עָנֵר אֶשְׁכֹּל וּמַמְרֵא, הֵם יִקְחוּ חֶלְקָם.  {ס}

In terms of the place name spelled chaser, we have the present first pasuk, in pasuk 23:

במדבר פרק יג

• פסוק כ"ג: וַיָּבֹאוּ עַד-נַחַל אֶשְׁכֹּל, וַיִּכְרְתוּ מִשָּׁם זְמוֹרָה וְאֶשְׁכּוֹל עֲנָבִים אֶחָד, וַיִּשָּׂאֻהוּ בַמּוֹט, בִּשְׁנָיִם; וּמִן-הָרִמֹּנִים, וּמִן-הַתְּאֵנִים. 

We also have an example in sefer Devarim 1:24:

 כד וַיִּפְנוּ וַיַּעֲלוּ הָהָרָה, וַיָּבֹאוּ עַד-נַחַל אֶשְׁכֹּל; וַיְרַגְּלוּ, אֹתָהּ.  כה וַיִּקְחוּ בְיָדָם מִפְּרִי הָאָרֶץ, וַיּוֹרִדוּ אֵלֵינוּ; וַיָּשִׁבוּ אֹתָנוּ דָבָר, וַיֹּאמְרוּ, טוֹבָה הָאָרֶץ, אֲשֶׁר-יְהוָה אֱלֹהֵינוּ נֹתֵן לָנוּ.

where the place is called chaser, but it is before they actually take the fruit.

In terms of Eshkol spelled malei, we have pasuk 24:

במדבר פרק יג

• פסוק כ"ד: לַמָּקוֹם הַהוּא, קָרָא נַחַל אֶשְׁכּוֹל, עַל אֹדוֹת הָאֶשְׁכּוֹל, אֲשֶׁר-כָּרְתוּ מִשָּׁם בְּנֵי יִשְׂרָאֵל. 

and a reference to the fruit in sefer Michah:

מיכה פרק ז

• פסוק א: אַלְלַי לִי, כִּי הָיִיתִי כְּאָסְפֵּי-קַיִץ, כְּעֹלְלֹת, בָּצִיר:  אֵין-אֶשְׁכּוֹל לֶאֱכוֹל, בִּכּוּרָה אִוְּתָה נַפְשִׁי. 

The one confounding pasuk with this theory is in Bemidbar 32:

במדבר פרק לב

• פסוק ט: וַיַּעֲלוּ עַד-נַחַל אֶשְׁכּוֹל, וַיִּרְאוּ אֶת-הָאָרֶץ, וַיָּנִיאוּ, אֶת-לֵב בְּנֵי יִשְׂרָאֵל--לְבִלְתִּי-בֹא, אֶל-הָאָרֶץ, אֲשֶׁר-נָתַן לָהֶם, יְהוָה. 

There, it is spelled malei even though it is before they took the fruit. And if you answer it is spelled malei based on the eventual happening, then we can say all this without the Vilna Gaon's neat theory, and apply it simply in parashat Shelach, ignoring any malei chaser difference.

So that is the first "problem" I have with the Gra's rather creative theory. The second "problem" is that I feel that he extrapolates too much from his two examples, regarding plural vs. singular and malei vs. chaseir. Recall, his two examples are
בסכת בסכת בסכות
 קרנת קרנת קרנות

From here, one can extrapolate a rule about malei and chaser and plural and singular, because Chazal count the malei as two and the chaser as one. That rule can either be:
(1) If it ends in ות, it is plural, while if it ends in ת, is it singular.
or, it can be
(2) If is has a cholam malei, it is plural, while if it has a cholam chaser, it is singular.

The first is a more conservative rule. And tafasta meruba, lo tafasta; tafasta muat, tafasta. I don't think that there is enough evidence to extrapolate to the general case.

Another example:
איתמר רב אסי אמר חתיכה אחת שנינו ספק של חלב ספק של שומן חייא בר רב אמר חתיכה משתי חתיכות שנינו במאי קא מיפלגי רב אסי סבר יש אם למסורת (ויקרא ה) מצות כתיב וחייא בר רב אמר יש אם למקרא מצוות קרינן

Another example:

ר"ע דתניא ר"ע אומר מניין לרביעית דם שיצאה משני מתים שמטמא באהל שנאמר (ויקרא כא) על כל נפשות מת לא יבא שתי נפשות ושיעור א' ורבנן נפשת כתיב

The Gra knows quite well that it is always involving an ות ending vs. a ת ending.

If so, what is its explanation? That when it is spelled malei, then it clearly is pronounced malei, and -ot is an ending in Biblical Hebrew which connotes plural. Meanwhile, if spelled chaseir, then it can be pronounced as, e.g., karnat, with a patach. This is singular, though quite awkward, since it is the construct form of the noun, instead of the absolute. But this awkwardness is allowed, since after all, there is a derasha in play. This is then not only an arbitrary rule (such as cholam malei vs. cholam chaser), but an explanation of that rule which makes some sense.

I don't see compelling evidence for the Gra's more expansive rule, as well as an assumption that the difference between pronunciation between cholam chaser vs. cholam malei really connoted that. Give me some prooftexts from Chazal, and then I can consider it.

To sum up, I don't think that there is a real question on a peshat level, for Ibn Ezra already addressed the issue quite well. If one asks the question seriously, and does not dismiss it in Ibn Ezra's peshat way, then the Gra has an interesting answer. However, it does not seem to be borne out by the pesukim, since we have that counterexample in Bemidbar 32. And the Gra's evidence of this expansive rule is unpersuasive, and takes us away from the simpler, more meaningful explanation of that rule.