Rashi explains that the tribes among whom the leaders grew up and lived would know them better than Moshe Rabbeinu did. Moshe said, “If each of them were to come before me wrapped in his Tallis, I would not know who he is, from which tribe he has descended, and if he is worthy.” In other words, apparently Moshe had difficulty discerning the pedigree and true nature of each judicial candidate. This seems inconsistent with the pasuk in Sefer Shemos 18:21, in which Moshe is told to “seek out men of ability,
G-d-fearing men of truth who hate improper gain.” Rashi explains that he should search out these men by using his Heavenly endowed powers of Ruach HaKodesh, Divine Inspiration. If Moshe is able to discern “who is who” by using his spiritual powers, why did he ask the people for their input?
Horav Yaakov Galinsky, zl, teaches us an important lesson, which sadly, all too often, proves itself valid. He explains that Moshe himself circumvented this question when he said, “For if he will come before me covered in his Tallis, I will not know who he is.” Indeed, Yitzchak Avinu was certainly endowed with Ruach HaKodesh, yet Eisav was able to pull the proverbial wool over his eyes. How did he do it? Chazal teach us that he came before his father dressed in his finery – clothing that quite possibly concealed the real Eisav. He would present himself to his father dressed as a Torah scholar, bent over in humility, speaking with spiritual refinement. In other words, Eisav disguised himself when he came to Yitzchak.
Likewise, Moshe was concerned that a potential candidate would disguise his true self. The people with whom he had grown up knew how he really dressed, what his habits, true religious leanings, and moral compass were.
Chazal teach that le’asid lavo in Olam Habba, the World to Come, Eisav will enter dressed in his Tallis as everyone else and claim his seat right next to Yaakov Avinu – after all… This is the meaning of misatef b’Talliso, wrapped in his Tallis, concealing his many moral and spiritual faults.
Rav Galinsky relates that he once had occasion to ask information from the Gerrer Rebbe, zl, the Bais Yisrael, concerning one of his chassidim. “What would you like to know?” the Rebbe asked. “I would like to know about his level of yiraas Shomayim, fear of Heaven,” Rav Galinsky replied.
“How should I know?” asked the Rebbe. “Concerning yiraas Shomayim, only two know the real truth: Hashem and his wife!”
