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.
the descendants of Ishmael [i.e., the Bedouin], asking of them:
Will you accept the Torah?
They asked: What’s written in it?
“Do not steal” (Ex.20:13)
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
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.
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.