For an explanation of the methodology of this series, see the introduction.

"They went up in the south, and he came to Hebron, and there were Achiman, Sheshai, and Talmai, the descendants of the giant. Now Hebron had been built seven years before Zoan of Egypt. " (Num. 13:22)

Peshat (basic meaning) :

Rashi: "and he came to Hebron"
Caleb went there alone [hence the singular "he came"] to prostrate himself on the graves of the patriarchs [in prayer] that he not be enticed by his colleagues to be part of their counsel. Thus, it says, "I will give him [Caleb] the land on which he has walked" (Deut. 1:36) and it is written, "They gave Hebron to Caleb". (Jud. 1:20)

The intention is to inform you of the excellence of the Land of Israel...

"had been built seven years"
Is it possible that Ham built Hebron for Canaan, his youngest son, before he built Zoan for Mitzrayim, his eldest son? Rather, it was stocked with everything good, seven times more than Zoan. The intention is to inform you of the excellence of the Land of Israel, for there is no place in the Land of Israel rockier than Hebron, which was why it was designated for a burial ground. And there is no country in the world as excellent as Egypt, as it says, "it was like the garden of the Lord, like the land of Egypt". (Gen. 13:10) Zoan is the best part of Egypt, for the residence of the kings is situated there, as it says, "for his princes were in Zoan". (Isa. 30:4) Yet Hebron was superior to it seven times over.

Remez (hinted meaning):

Baal HaTurim: "Hamat. They ascended in the south and he arrived."
When their order is reversed, the final letters of these 4 words spell 'Avot/Patriarchs'. For Caleb went alone to the Cave of Machpelah in Hebron and prostrated himself in prayer at the grave of the patriarchs.

Derash (interpretive meaning):

Bamidbar Raba: The sight of the 3 giants Achiman, Sheshai and Talmai inspired the spies with terror. They were so tall that the sun only reached their ankles. When anyone would see Achiman coming, they would imagine that a mountain was falling on them. Sheshai seemed as strong as marble [shayash] and Talmai's feet threw up huge plots of land when he walked, thus his name means "plots."

Maggid Mesharim: Caleb replied to them: (Ibid. 13:30) "Let us certainly go up and we will take possession of it," that it is impossible that the Land will consume us for G‑d gave it to us, certainly with the knowledge that we will survive on the land that he gave us. This is what is meant by "and we will take possession of it", and (Ibid. 14:9) "you do not fear the people of the land." Even though the text should not be taken out of its simple context, and the verb ‘tiru/fear comes from yireh/ "fear", nevertheless there are explanations of it based on the word ‘riyah’/sight. The meaning in such a case is: do not see yourselves as people of the land, i.e. as weak persons, because we are stronger than they are. The proof of this is "for they are our bread" (ibid.) that is, they have already been given over to our hands, and it is known that whoever is nourished, whoever eats the food, is stronger than what nourished him, than the food itself, for the one who nourishes consumes the food that nourishes him. Since they are our food, even though they are strong, we are certainly stronger than they are.
...even if we are weak, we will survive there...
Also, what you spies said that they are strong — that is not the truth. For this year, their shelter has left them, and this was their power. Even though they survive on the Land, the Land is not consuming them, so it is not a land that consumes its inhabitants even though they are weak. Thus, even if we are weak, we will survive there and it will not consume us.

Ramban: I disagree with Rashi. Hebron is Kiryat-arba, the greatest man of the Anakim having the name Arba, and it was he who build Hebron, and that is why it was called by his name. He had a son named Anak, and after that all the inhabitants were called Anakim.

The Isbitzer Rebbe: Caleb
The Zohar mentions 3 worlds of spiritual penetration: one world is deeply hidden and not known to us at all; one world is already known constantly; and one world is available but can be much more available with preparation and holy grace. So too in one's life there are: some times we don't require spiritual practice to be in the flow; some times we won't benefit from spiritual practice even if we try; and some times we will benefit significantly from spiritual practice if we do it and will lose its benefits if we don't do it. Caleb knew about himself that it was the right time for him to practice. He fortified himself with prayer and visits to ancient burial mounds. That was his way. Yehoshua knew he didn't need to do even this. Sometimes we are like Joshua and others like Caleb. It is up to us to know when we need to do spiritual practice and just which kind will serve us best. (Gloss of R. David Wolfe Blank)

Sod (esoteric, mystical meaning):

Zohar Shelach 158:
"These are the names of the men whom Moses sent... " (Num. 13:4) Rabbi Yitzhak said: Moses observed and was aware that they would not succeed in their mission, and he then prayed about Joshua. Caleb was then in distress. He said: What shall I do, since Joshua goes forth with the utmost help of Moses, that he inspired in him the illumination of the moon. He shone upon him with his light in his prayer, since he is the sun. So what did Caleb do? He dropped back from them, and came to the burial place of the patriarchs, and prayed his prayer there.
...Caleb went a different way and took winding paths.
Rabbi Yehuda said: Caleb went a different way and took winding paths. He reached the burial plots of the patriarchs and endangered himself, as 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.

BeRahamim LeHayyim:
When will I merit the revelations of our ancestors? That is the question that the Baal Shem Tov asks us to ponder. When can I align myself on the right with Abraham, on the left with Yitzhak, and on center with Yaakov? When can I avoid being skewed to the right like Ishmael, or skewed to the left like Esau? What must I do to internalize the lessons of the patriarchs, those we review yearly in the Book of Genesis?

Caleb, whose name hints to Ce-Lev, "like the heart", or Celev — "dog" ("man's most loyal friend") — his loyalty to his ancestors, listened to the small silent voice, perhaps because his heartspace too was on high.

The binding of Caleb to the grave site of the patriarchs steered him in the right path, assured him to trust in his good instincts, and paved the way for him to have success in all his ways.

So too may we follow his example. G‑d desires the heart.

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