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I saw in the Midrash Tanchuma on Parshas Bamidbar the following:

(Source provided by Sefaria.org)

אָמַר לָהֶם הַקָּדוֹשׁ בָּרוּךְ הוּא, בָּעוֹלָם הַזֶּה, נִתְאַוֵּיתֶם לִדְגָלִים, וּמִלֵּאתִי מִשְׁאֲלוֹתֵיכֶם. וְלֶעָתִיד לָבֹא, בִּזְכוּת הַדְּגָלִים אֲנִי גּוֹאֵל אֶתְכֶם, וּמְדַלֵּג עַל הַקֵּץ בִּזְכוּת אָבוֹת שֶׁנִּקְרְאוּ הָרִים, שֶׁנֶּאֱמַר: קוֹל דּוֹדִי הִנֵּה זֶה בָּא, מְדַלֵּג עַל הֶהָרִים, מְקַפֵּץ עַל הַגְּבָעוֹת (שה״ש ב, ח

G-d said to them (the Children of Israel): In this world you desired for flags (for your tribes) and I fulfilled your request. In the future, because of the merit of those flags I will redeem you. As the verse states "Hark! My beloved! There he comes, Leaping (מדלג) over mountains, Bounding over hills." (Shir HaShirim 2:8)

Is there anything written about the reason for why the flag serves a merit for the children of Israel to be redeemed?

Update:

I saw in the footnotes of the Artscroll Chumash with Rashi 1 unlike other commentaries who understand the word דגל as "flag" Rashi sees it as a "division, disposition of forces, military formation"

While this is insightful it still does not answer the question of why the divisions/flags of Israel serve as a merit to be redeemed. But definitely something to take note of.

1 See Bamidbar pg. 9 footnote 3 for the entire context

  • You only want written sources or would a quote from a drasha suffice? – user6591 May 24 '17 at 0:02
  • @user6591 I would like to get written sources – TrustMeI'mARabbi May 24 '17 at 2:59
  • I saw that Rabbeinu Bachye has quite a lengthy piece. – TrustMeI'mARabbi May 24 '17 at 3:36
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    I can think of a few sevaros that I've heard, but I don't have any sources offhand. – DonielF May 28 '17 at 23:46
  • That Rabbeinu Bachaye elaborates on a related Midrash that describes the individual flags - their colors and designs - and he explains how each one is befitting of each sheet – DonielF May 28 '17 at 23:47
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There can be many meanings to this Midrash. Here are a couple of suggestions that could use some nice development and make a very beautiful Devar Torah (in fact, I may do so myself!). (Please note that some of these were written before I found the sources, others only after.):

  • A degel, or flag, unites Klal Yisrael around it (see Rashi above). Only once there is achdus will we merit Mashiach. (suggested here)
  • A flag is something used to show allegiance to a party, place, or in this case, Hashem. When we proudly wave "Hashem's flag", meaning, we show our allegiance to him and broadcast his message in this world, we will be redeemed. (suggested here, but he adds the nice thought that just as flags vary, so too we each have our own ways of serving Hashem)
  • A flag is something that has no power of its own, and is simply waved around by whatever or whomever is holding it. Since in various Midrashim, we dedicated ourselves to be Hashem's flags, we will be redeemed. (suggested here)

Notably, Shir Hashirim 2:4 (Alhatorah translation) states:

הֱבִיאַנִי אֶל בֵּית הַיָּיִן וְדִגְלוֹ עָלַי אַהֲבָה. He hath brought me to the banqueting-house, And his banner over me is love.

Mefarshim there (link above) explain as follows:

Rashi - gathering me in to him

Lekach Tov - Talmidei Chachamim are the "flags" of Torah, and Hashem will bring them to the Beis Hamikdash

Akedas Yitzchak - Public display of love between Hashem and Yisrael

See Torah Temimah there as well for a variety of derashos.

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