32. Rabbi Yehuda said: Caleb went a different way and took winding paths, MEANING THAT HE FOLLOWED TWISTED PATHS. He reached the burial plots of the patriarchs and endangered himself, as it is written: "Where Ahiman, Sheshai, and Talmai, the children of Anak, were" (Ibid. 22). However, just as someone in distress does not pay attention to anything, so too it was with Caleb. Because he felt distress, he was not observant, and came to pour his prayers upon the burial plots of the patriarchs, in order to be saved from the counsel OF THE SPIES.
39. Rabbi Yitzchak said, "AND (HE) CAME" MEANS whoever is more important than the rest, it enters into him; THAT IS, THE SHECHINAH ENTERED AND WAS CLOTHED IN CALEB since upon it, ON THE SHECHINAH, everything depends. Come and see: Who has the advantage over the rest, to be able to come there, TO HEBRON, since it is written: "And there were Ahiman, Sheshai, and Talmai." As a result of fearing them, who would be able to come EVEN TO HIDE in the cave? But the Shechinah was clothed there in Caleb to bring tidings to the Patriarchs. The time has arrived for their children to enter the land which the Holy One, blessed be He, had sworn to them, and that is why he: "came to Hebron." IT DOESN'T SAY, "AND THEY CAME," SINCE IT ALLUDES TO THE SHECHINAH.
40. From whom were Ahiman, Sheshai and Talmai descended? They were the offspring of the Nefilim (lit. 'fallen ones') that the Holy One, blessed be He, dropped FROM THE HEAVEN to the earth, and they produced offspring from the daughters of the earth. From them emerged the mighty men of old, as it is written: "The same were mighty men of old, men of renown" (Beresheet 6:4). "Of old" MEANS they were present from the time the world was created and "men of renown" are Ahiman, Sheshai and Talmai, MEANING THAT THEIR NAMES WERE WELL KNOWN IN THE WORLD.
60. Following that: "and (he) came to Hebron," MEANING that he has come to adhere to the Torah, and he reads and studies it. "Where Ahiman, Sheshai and Talmai..." (Bemidbar 13:22), MEANING he sees there many divisions: unclean and clean, forbidden and permitted, punishment and recompense. These are the paths of the Torah, the specifics of the Torah. "The children of Anak" (Ibid.): MEANING THAT they were born from the side of Gvurah.