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

"Prepare for yourselves wise and understanding men, known among your tribes, and I will make them heads over you." (Deut. 1:13)

Peshat (basic meaning):

Rashi: "prepare for yourselves"
Prepare yourselves for this matter.

"understanding [men]"
"A wise man is like a rich money changer..." [i.e. men] who understand [and derive] one thing from another. This is what Arius asked Rabbi Yose: "What is the difference between wise men and understanding men?" [Rabbi Yose said] "A wise man is like a rich money changer: When people bring him dinars to examine, he examines them. When they do not bring [money] to him, he sits doing nothing. An understanding man, however, is like a merchant money changer: When they bring him money to examine, he examines it, and when they do not bring it to him, he goes out and brings his own [money - i.e., he does not wait for people to come to him, he goes to them]

"well-known among your tribes"
Men whom you recognize, for if one were to come before me wrapped in his tallit, I would not know who he is and of what tribe he is, and whether he is suitable. But you know him, for you have raised him. Therefore, it says, "well-known among your tribes."

"and I will make them heads over you"
As chiefs and respected persons over you, i.e., you should act towards them with respect and reverence. This teaches us that Israel’s transgressions are hung over the heads of their judges, since they [the judges] should have prevented them [from sinning] and direct them along the right path.

Remez (hinted meaning):

Baal HaTurim: "And I shall place them as your heads"
The word "Va’asimam/I shall place them" is spelled defectively, without a yud (= 10). This indicates to you that the Torah admonished 10 times regarding judges. Alternatively, it is spelled defectively to indicate to you that the guilt lies with the head leaders, for it is within their power to protect yet they did not protest.

Derash (interpretive meaning):

Ohr HaChayim: He used the word "for yourselves" before mentioning that they should be from their respective tribes as the fact that the judges were selected from within their respective tribes resulted in many beneficial effects for the members of the tribes.

"and I will place them as heads over you":
Although Moses told the people that the appointment of these judges would be for their benefit, i.e. that they themselves would be allowed to select these judges, the fact remained that these judges would exert their authority over the people, if necessary, by means of force.

Mei HaShiloah: In this verse, Moses proposes to appoint wise, understanding, and reputable individuals to be leaders over the tribes. In verse 15 he appoints only wise and reputable ones. What happened to the understanding ones? In the ninth verse, Moses said, "Eicha esa l'vadi/How can I bear your troubles by myself?" In every parasha, the 9th verse carries additional depth beyond the simple meaning. What is the depth here?
The 'Eicha'-cry of Moses hints to the Eicha of Jeremiah the prophet...
The 'Eicha'-cry of Moses hints to the Eicha of Jeremiah the prophet which opens the Book of Eicha/Lamentations read on Tisha B'Av: "Eicha Yashvah badad/How can Jerusalem sit alone?" Moses let us know well in advance that there would be times when we would scream "Eicha, how could this have happened? Part of the answer is that he could find no one of bina/understanding who could explain "Eichah/how?"

According to Kabbalah, the word for this month Av, also meaning 'father,' stands for chochma/wisdom, as it exists without softening by bina/understanding. Bina represents Imma/mother, who reflects and contains until understanding is squeezed out with any drops of sweet sorrow. This is compassion in action.

Chochma, however, is a flash of idea, without such "patience". Chochma and bina are 2 friends who never separate, and work well. But when bina has no chochma, it might hold on forever. When chochma has no bina as in the month of Av, it may break situations without motherly compassion Thus the wail of Eichah/How can this have happened? How can there be wisdom without compassion?

Sod (esoteric, mystical meaning):

Zohar Vayakhel 201:
Afterwards, Rabbi Yosi opened with the following verse: "And every wise hearted individual among you shall come and make." (Ex. 35:5) We already explained this text but come and see: when G‑d said to Moses "Take wise and understanding men", he searched throughout Israel but did not find men of understanding. This is why, "So I took the chief of your tribes, wise men, and known," (Ibid. 15) but 'understanding' is not mentioned. You might say that understanding is in a grade superior to wisdom, and this of course is right.

What is the difference between them? We explained about a wise man, that even a pupil who imparts wisdom to his rabbi is considered wise. A wise man knows for himself what ought to be done. A man of understanding has many levels in him, because he examines everything and knows for himself and for others. You may derive this from "A righteous man regards the life of his beast". (Prov. 12:10) And also "righteous ruling in the fear of Elokim." (II Samuel 23:3) And here, "wise hearted" is precise, Man is wise in his heart, and not elsewhere, because wisdom lies in the heart. But a man of understanding exist both above and below, and observes himself and others.

BeRahamim LeHayyim:
Chochma/wisdom, bina/understanding, and da'at/applied Knowledge are 3 different things. 'Rabbi Eliezer the son of Azariah would say: If there is no chochma/wisdom, there is no fear of G‑d; if there is no fear of G‑d, there is no chochma/wisdom. If there is no da'at/ applied knowledge, there is no bina/understanding; if there is no bina/understanding, there is no da'at/ applied knowledge." (Avot 3:10)
Mentalities lacking integration are like islands in the sea...
We need integration. Mentalities lacking integration are like islands in the sea, each powerful and rich in resources, but isolated, and unable to assist the greater whole.

Perhaps what the Zohar is telling us is that although chochma is more sublime, more intuitive, and "higher" in absolute and abstractness, that da'at is in a sense "higher" in that it is concrete, it is of this world, and it is practical. We should not be so spiritually minded that we are of no earthly good.

Bina means to be able to discern the trees from the Forest, to be able to uses the left-brain for real life problem solving. Da'at takes this and puts it into action, applies the knowledge of chochma and the analysis of bina, marries them together, and voila, we have a product!

Chochma is parsed as koach mah, lit. "the power of What?" Bina, however, asks a more refined question of "Mi/Who?", Mi having a gematria of 50, representing bina's 50 gates.
Not "What is this?", but rather "Who's going to get the job done?!"

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