The association of Jacob – Yaakov with a heel is strange. Jacob is not the only mythical hero with a famous heel, but in Achilles case, he was the owner of the heel. Jacob’s relationship with his brother’s heel is vicarious. If the biblical author, let alone his parents, want to be flattering, they do a lousy job. Jacob is to be known, at best, as a “hanger on”. Fox’s translation: "Heel-Holder"
Even if we choose to think of Jacob as a bootstrapper, we can’t forget that he pulls himself up by a bootstrap attached to his brothers heal. And let’s not forget that Esau’s heal, like Achilles, is his most vulnerable body part. Metaphorically, the heel is the exposed rear of an army (see Joshua 8:13 and Genesis 49:19). When God curses the snake for tempting Eve, it is on the snake's metaphorical heel that man shall forever stamp (Genesis 3:15). Attacking an enemy’s heel is an insult to both the attacker and the victim.
Strong's Lexicon: Ekev https://www.blueletterbible.org/lexicon/h6119/kjv/wlc/0-1/
(יג) וַיָּשִׂ֨ימוּ הָעָ֜ם אֶת־כׇּל־הַֽמַּחֲנֶ֗ה אֲשֶׁר֙ מִצְּפ֣וֹן לָעִ֔יר וְאֶת־עֲקֵב֖וֹ מִיָּ֣ם לָעִ֑יר וַיֵּ֧לֶךְ יְהוֹשֻׁ֛עַ בַּלַּ֥יְלָה הַה֖וּא בְּת֥וֹךְ הָעֵֽמֶק׃
(13) Thus the main body of the army was disposed on the north of the city, but the far end of it was on the west. (This was after Joshua had spent the night-a in the valley.)—
But he shall raid at their heels.
(טו) וְאֵיבָ֣ה ׀ אָשִׁ֗ית בֵּֽינְךָ֙ וּבֵ֣ין הָֽאִשָּׁ֔ה וּבֵ֥ין זַרְעֲךָ֖ וּבֵ֣ין זַרְעָ֑הּ ה֚וּא יְשׁוּפְךָ֣ רֹ֔אשׁ וְאַתָּ֖ה תְּשׁוּפֶ֥נּוּ עָקֵֽב׃ {ס}
(15) I will put enmity
Between you and the woman,
And between your offspring and hers;
They shall strike at your head,
And you shall strike at their heel.”
He approached
the descendants of Ishmael [i.e., the Bedouin], asking of them:
Will you accept the Torah?
They asked: What’s written in it?
He replied:
“Do not steal” (Ex.20:13)
They said:
The very essence of these people, like their father, is banditry.
For it is said:
“And he shall be a wild ass of a man” (Gn.16:12).
Sifrei Devarim ve'zot Habracha Pisqa’ 343
"Oh, Master, make me chaste and celibate - but not yet!"
da mihi castitatem et continentam, sed noli modo
book eight, chapter seven of Augustine's Confessions
גמ׳ גזול .... אמאי לא
א"ר יוחנן משום רבי שמעון בן יוחי
GEMARA: The ruling in the mishna is that a stolen lulav is unfit. ....why does one not fulfill his obligation with a stolen lulav?
Rabbi Yoḥanan said in the name of Rabbi Shimon ben Yoḥai:
משום דהוה ליה מצוה הבאה בעבירה שנאמר (מלאכי א, יג) והבאתם גזול ואת הפסח ואת החולה גזול דומיא דפסח מה פסח לית ליה תקנתא אף גזול לית ליה תקנתא לא שנא לפני יאוש ולא שנא לאחר יאוש
בשלמא לפני יאוש (ויקרא א, ב) אדם כי יקריב מכם אמר רחמנא ולאו דידיה הוא אלא לאחר יאוש הא קנייה ביאוש אלא לאו משום דהוה ליה מצוה הבאה בעבירה
וא"ר יוחנן משום ר' שמעון בן יוחי מאי דכתיב (ישעיהו סא, ח) כי אני ה' אוהב משפט שונא גזל בעולה משל למלך בשר ודם שהיה עובר על בית המכס אמר לעבדיו תנו מכס למוכסים אמרו לו והלא כל המכס כולו שלך הוא אמר להם ממני ילמדו כל עוברי דרכים ולא יבריחו עצמן מן המכס אף הקב"ה אמר אני ה' שונא גזל בעולה ממני ילמדו בני ויבריחו עצמן מן הגזל
ופליגא דר' יצחק דא"ר יצחק בר נחמני אמר שמואל לא שנו אלא ביום טוב ראשון אבל ביום טוב שני מתוך שיוצא בשאול יוצא נמי בגזול
It is unfit because it is a mitzva that comes to be fulfilled by means of a transgression, which renders the mitzva unfulfilled, as it is stated: “And you have brought that which was stolen and the lame, and the sick; that is how you bring the offering; should I accept this of your hand? says the Lord” (Malachi 1:13). Based on the juxtaposition in the verse, it is derived that the legal status of a stolen animal is equivalent to that of a lame animal. Just as a lame animal, because it is blemished, has no remedy and is unfit for use, so too, a stolen animal has no remedy. There is no difference before the owners reach a state of despair of recovering the stolen animal, and there is no difference after despair. In both cases there is no remedy.
The Gemara elaborates: Granted, before the despair of the owner, the robber may not sacrifice the animal because the animal does not belong to him. The Merciful One says: “When a person sacrifices from yours an offering” (Leviticus 1:2). The term “from yours” indicates that the animal must belong to the one sacrificing it, and this stolen animal is not his. However, after the despair of the owner, didn’t the robber acquire the animal with the despair? Once the owner despairs, the animal belongs to the robber, despite the fact that he incurs a debt that he must repay the owner. Since the animal is legally his, why is it prohibited for the robber to sacrifice it as an offering? Rather, is it not because the offering is a mitzva that comes by means of a transgression? Since the animal came into his possession by means of a transgression, it is unfit for use in fulfilling a mitzva.
And Rabbi Yoḥanan said in the name of Rabbi Shimon ben Yoḥai: What is the meaning of that which is written: “For I the Lord love justice, I hate robbery in a burnt-offering” (Isaiah 61:8)? The Gemara cites a parable of a flesh-and-blood king who was passing by a customs house. He said to his servants: Pay the levy to the taxmen. They said to him: Doesn’t all the tax in its entirety belong to you? If the taxes will ultimately reach the royal treasury, what is the point of paying the levy? He said to them: From my conduct, all travelers will learn and will not evade payment of the tax. So too, the Holy One, Blessed be He, said: “I the Lord... hate robbery in a burnt-offering.” Although the whole world is His and the acquisitions of man have no impact upon Him, God says: From My conduct, My children will learn and distance themselves from robbery, even from robbery unrelated to the needs of offerings.
“Out of the crooked timber of humanity, no straight thing was ever made.”
― Immanuel Kant, Idea for a Universal History with a Cosmopolitan Purpose
(ג) גּ֚וּר בָּאָ֣רֶץ הַזֹּ֔את וְאֶֽהְיֶ֥ה עִמְּךָ֖ וַאֲבָרְכֶ֑ךָּ כִּֽי־לְךָ֣ וּֽלְזַרְעֲךָ֗ אֶתֵּן֙ אֶת־כׇּל־הָֽאֲרָצֹ֣ת הָאֵ֔ל וַהֲקִֽמֹתִי֙ אֶת־הַשְּׁבֻעָ֔ה אֲשֶׁ֥ר נִשְׁבַּ֖עְתִּי לְאַבְרָהָ֥ם אָבִֽיךָ׃ (ד) וְהִרְבֵּיתִ֤י אֶֽת־זַרְעֲךָ֙ כְּכוֹכְבֵ֣י הַשָּׁמַ֔יִם וְנָתַתִּ֣י לְזַרְעֲךָ֔ אֵ֥ת כׇּל־הָאֲרָצֹ֖ת הָאֵ֑ל וְהִתְבָּרְכ֣וּ בְזַרְעֲךָ֔ כֹּ֖ל גּוֹיֵ֥י הָאָֽרֶץ׃ (ה) עֵ֕קֶב אֲשֶׁר־שָׁמַ֥ע אַבְרָהָ֖ם בְּקֹלִ֑י וַיִּשְׁמֹר֙ מִשְׁמַרְתִּ֔י מִצְוֺתַ֖י חֻקּוֹתַ֥י וְתוֹרֹתָֽי׃
(3) Reside in this land, and I will be with you and bless you; I will assign all these lands to you and to your heirs, fulfilling the oath that I swore to your father Abraham. (4) I will make your heirs as numerous as the stars of heaven, and assign to your heirs all these lands, so that all the nations of the earth shall bless themselves by your heirs— (5) inasmuch as Abraham obeyed Me and kept My charge: My commandments, My laws, and My teachings.”
The word translated as “because” or "inasmuch" is “ekev”. Used in this fairly rare sense, it has the sense of “as a consequence, a gain, a reward, end”. It is that which results from a long, tedious, painful, tortuous and circuitous journey. A pilgrimage full of blisters and maybe a touch of plantar fasciitis. Esau, might have been, like Achilles, the golden boy and favorite son and Yaakov, the parasite, but Yaakov struggled with what little he had. Esau may have been well heeled, but Yaakov had the fortitude and faith in a God of history to grab steadfastly for a better future.
(לו) וַיֹּ֡אמֶר הֲכִי֩ קָרָ֨א שְׁמ֜וֹ יַעֲקֹ֗ב וַֽיַּעְקְבֵ֙נִי֙ זֶ֣ה פַעֲמַ֔יִם אֶת־בְּכֹרָתִ֣י לָקָ֔ח וְהִנֵּ֥ה עַתָּ֖ה לָקַ֣ח בִּרְכָתִ֑י וַיֹּאמַ֕ר הֲלֹא־אָצַ֥לְתָּ לִּ֖י בְּרָכָֽה׃
(36) [Esau] said, “Was he, then, named Jacob that he might supplant me these two times? First he took away my birthright and now he has taken away my blessing!” And he added, “Have you not reserved a blessing for me?”
Here Ekev-heel is used in the sense of “to throw one down, to trip one up, to supplant, to circumvent, to defraud.[iii] Fox’s translation: "Heel-Sneak".
(ג) אִ֤ישׁ מֵרֵעֵ֙הוּ֙ הִשָּׁמֵ֔רוּ וְעַל־כׇּל־אָ֖ח אַל־תִּבְטָ֑חוּ כִּ֤י כׇל־אָח֙ עָק֣וֹב יַעְקֹ֔ב וְכׇל־רֵ֖עַ רָכִ֥יל יַהֲלֹֽךְ׃
Trust not even a brother!
For every brother takes advantage,
Every friend is base in his dealings.-a
What kind of parents would the biblical author have Isaac and Rebecca be? Who gives a child such a name?
Clearly, Jacob is in need of a name change… and in fact, this is what happens after he wrestles with the Angel at the River Jabbok (literally: wrestling river).
There is nothing flattering that one can say about Yaakov’s name. His name can only portend a change. A change from a swindler, a scrapper, a kniver… someone who by choice or circumstance is forced to steal his blessings and eke out a living and a life. Yaakov is the outsider, the Ghetto Jew, but his name portends another name, where he crosses the river into his homeland and can stand on his own feet and pull himself up from his own bootstraps ... attached to his own heel. This is what hopefully lies ahead for him in his future name and this is what presumably is up for grabs in the blessing that he steals.
Every hill and mount made low.
Let the rugged ground become level
And the ridges become a plain.
And the commentators have said that the meaning of the word eikev is that “in the end” there will be reward. Similarly, in keeping them [the ordinances of G-d] ‘eikev rav’ (there is [in the end] great reward). The verse here is thus stating: “and the end [the ultimate consequence] of your hearkening to the ordinances and your observing them is that G-d shall keep the covenant and the mercy, and He will love thee. ” This is correct, for in the Sacred Language the beginning of anything is called rosh [literally: “head”], as it is said, ‘rosh’ (the beginning of) Thy word is truth. So also is the leader of the generation called “the head of the people,” and the best of spices is called rosh. Similarly, the conclusion of any matter is called akeiv (heel) as the Sacred Language adopts these figurative expressions from the human body; and thus “the head” is the beginning while “the heel” is the conclusion and end of the body. Scripture also speaks of the head and the tail [with reference to people], figuratively using the body of the animal.
And Onkelos rendered the word eikev as chalaf (“in exchange for”), like ‘cheilef’ (in return for) your service. Onkelos thus made it an expression of “roundabout” [the end result of a series of events], derived from the verse, and ‘he’akov (the crooked) shall be made straight — that is, the circuitous road which goes roundabout [will become a straight, level path]. So also ‘akubah’ of blood means “it is surrounded and encircled” [with blood]. The verse here is thus stating [according to Onkelos]: “and it shall come to pass that the effect caused by your hearkening to the ordinances and your performing them will be that G-d will keep His covenant with you.” He has explained it well. A similar expression is ‘biglal’ (for the sake of) this thing which means “on account of,” from the word ‘v’gal’lu’ (and they roll) the stone. Similarly it is my opinion that every expression of akeivah is a term denoting “circle” or “circuit.” Thus: ‘akov haleiv’ (the heart is deceitful); ‘vaya’akveini’ (and he hath gotten the better of me) these two times; but Jehu did it ‘b’akbah’ (in subtlety) — all these being expressions of “rolling” and “circling.” Therefore they called Jacob “Jeshurun” [from the root yashar (straight and upright)] because the opposite of “the deceitful one” is he who is “upright” [as indicated by the name “Jeshurun”]. Similarly, the end-part of the foot, called akeiv — as it is said, and his hand seizing ‘ba’akeiv (the heel) of Esau — is so called because of its roundness, just as the [Sacred] Language calls the middle part [palm and sole] of the hand and foot kapoth, because of their being shaped like golden kapoth (spoons). This usage [of the term akeiv] is common in the [Sacred] Language, just as the Rabbis have said in the Sifre: “At His right hand was a fiery law unto them. When the word came forth from the mouth of the Holy One, blessed be He, it would go by way of the right hand of the Holy One to the left of Israel, v’okeiv (and it encircled) the camp of Israel twelve miles by twelve miles.” So also is the expression: “they come upon him ba’akifin,” meaning “with circuitous and subtle arguments,” like the word akeivin as these two letters [the veth and the fei] were considered by the Sages to be interchangeable, as I have already explained.
He mentioned these ordinances in order to warn exceedingly concerning the ordinances [i.e., judgments], for it is impossible that of a large nation, everyone be heedful of all commandments so as not to transgress any of them, and it is only through the judgments [of the court] that they establish [the firm authority of] the Torah, just as it says of them, and all Israel shall hear, and fear. Moreover, many people will have pity [and refrain from] stoning a man or burning him after the transgression had been committed, as it is said, Thine eye shall not pity him. Then also they might fear the mighty ones as well as those who lead astray, as it is said, ye shall not be afraid of the face of any man, for the judgment is G-d’s, and in the case of the false prophet it says, thou shalt not be afraid of him. He mentioned all these in the case of an inciter [to worship idols] saying, thou shalt not consent unto him, nor hearken unto him; neither shalt thine eye pity him, neither shalt thou spare, neither shalt thou conceal him, warning nor hearken unto him because of his misleading [you], neither shalt thine eye pity him because of the pity that compassionate people show towards the condemned, and neither shalt thou conceal him by remaining silent [and not presenting testimony against him] because of his might and fear of members of his family.
“I will make most severe
Your pangs in childbearing;
In pain shall you bear children.
Yet your urge shall be for your husband,
And he shall rule over you.”