The gemara in Nedarim (58a) tells us that in order for the Shechina to rest on someone, he must have four attributes; wise, rich, strong, and modest. The Kli Yakar says that grouping of the encampment of Bnei Yisroel into four Degalim was to highlight these four attributes of Klal Yisroel so that the Shechina would rest on us.
The first Degel led by Yehuda represented wisdom or Torah. Yehuda was the Nasi and Reish Galusa who set the policies of the Torah, “Lo Yasur Shevet MiYehuda”. Yisachar learned Torah and Zevulun supported him making him an equal contributor of Torah or wisdom. They camped in the east where the sun rays first emanate in the morning just like Torah goes out from Tziyon.
The second Degel was that of Reuven who represented Anava or modesty. He was not embarrassed to admit his mistake and do Tshuvah for moving Yaakov’s bed. Along with him is Shimon who’s Shevet comprised of teachers, Sofrim, and poor people. This group is usually more modest than all others. Gad led the battles in Eretz Yisroel even though he only promised to join equally. His leading the battle was not out of haughtiness and he still acted humble as it says, “V’Hu Yagud Akeiv”, his legions went with humility like the heel of the foot. They camped in the south or Darom, which means “Dar Rom” living on high since Hashem lifts up all those who lower themselves.
The third Degel was Efraim joined by Menashe and Binyomin who represent strength. The pasuk says in Tehilim (80:3) “Lifnei Efraim, U’Binyomin, U’Menashe Orira Es Gevurasam”. They camped in the west where the sun sets, since strength wanes with time.
The last Degel was that of Dan who represented wealth. In fact they were so wealthy that their abundance of gold led to Avodah Zara. Asher was wealthy as well as it says, “Mei’Asher Shmeina Lachmo” and so was Naftali, “Naftali S’va Ratzon”. The attribute of wealth, says the Kli Yakar was the least important and therefore the Degel of Dan traveled last.
All four Degalim surrounded the Mishkan because these attributes were used only to serve Hashem and bring the Shechina down to Klal Yisroel..

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