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Zugger613
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Bamidbar: דגל התורה

The של״ה writes that the first three shevatim that traveled together, Yehuda, Yissachar, and Zevulun, represented the Torah.

Perhaps we can suggest that the names of the נשיאם of each Shevet give us a clue as to their unique contribution to the study and the spread of Torah.

The נשיא of Yehuda was נחשון בן עמינדב. Perhaps this shows that Nachshon and his shevet excelled in being שונה בנחת, teaching gently, the עם of Hashem (see שה״ש ז,ב where בנ״י are called בת נדיב). This can be seen in how Nachshon led by example, jumping into the ים סוף first.

The נשיא of Yissachar was נתנאל בן צוער. Perhaps this shows that the shevet of Yissachar would always toil in the Torah that Hashem gave (נתן קל) even when doing so entailed great sacrifice (צער).

The נשיא of Zevulun was אליאב בן חילון. Perhaps this shows that the shevet of Zevulun would always be focused on doing the will their Father in Heaven (אלי אב), even when they were doing things that were חול, seemingly mundane. Zevulun used their financial expertise to both support the Torah of Yissachar, and to show the nations of the world the beauty of Yiddishkeit.

לע״נ דוד חיים בן ישראל דוב הכהן
לע״נ ר׳ חיים דוב בן ר׳ בןציון שלום