https://www.yutorah.org/lectures/lecture.cfm/1066910/rabbi-ya-akov-trump/the-first-flag/
CHOCHMAS NASHIM: GRAND OLE FLAG
By: Suri Davis
In this week’s torah portion, B’haalotchah, there is mention of Israel moving with their flags. From whence came the flags and for what purpose?
Rabbi Yaakov Trump, Morah D’asrah of Young Israel of Lawrence Cedarhurst gave a spirited and poetic class last Sunday on the origination and meaning of the flag.
Doing the best I can to summarize what he said, which can be found at YUTorah.org, the origination of a flag came from the flags which were used to organize the angels in heaven, which the Jews wanted to organize themselves.
Fast forward to the early 1900s, when war broke out in Europe and Israel, Jews from Israel and Europe wanted to join the British in fighting the Axis, and they were permitted to organize their own Jewish legion to fight in the war. A flag was created for this special Jewish legion, and after WWII, the legion asked if the flag could be transplanted to Israel, and stored in a synagogue. The British permitted this transfer and on the day that the flag was installed in the largest shul in Israel, the Hurva, Rav Kook gave a poetic sermon on the meaning of a flag, and specifically what meaning there was for that flag to be brought into a makom kadosh in Eretz Yisrael.
Above is the URL for Rav Kook’s speech which is connected to the very comprehensive and beautiful lecture Rabbi Trump gave last week.
Good Shabbos.
-Suri