Ekev: Symbolism of Heels

וְהָיָ֣ה ׀ עֵ֣קֶב תִּשְׁמְע֗וּן אֵ֤ת הַמִּשְׁפָּטִים֙ הָאֵ֔לֶּה וּשְׁמַרְתֶּ֥ם וַעֲשִׂיתֶ֖ם אֹתָ֑ם וְשָׁמַר֩ יְהֹוָ֨ה אֱלֹהֶ֜יךָ לְךָ֗ אֶֽת־הַבְּרִית֙ וְאֶת־הַחֶ֔סֶד אֲשֶׁ֥ר נִשְׁבַּ֖ע לַאֲבֹתֶֽיךָ׃

Deuteronomy 7:12

Wherefore it shall come to pass, if you hearken to these judgments, and keep, and do them, that the Lord thy God shall keep unto thee the covenant and the troth which he swore to thy fathers:

Ekev literally means "heel" but it has four connotations:

"Caused by." In english the term "on the heels of" equally connects the bottom of the foot with the notion of causation.
Habit:
1. I would like to suggest that just as the feet often move the body without a person paying much attention, and sometimes we can step on things without paying attention, that the concept of habit is connection to the concept of the heel.
2. This explains the connection betwen the heel and the Snake and Jacob: Good habits save us from the snake.
3. Placing this implication back into the verse, we have a statement that Mitzvot and good behavior need to be habitaul to earn the blessings from them.
Actions. Adam represents Mankind perfected, and his "heels" represent the actions of all mankind. These eclipse that of th Sun, which represents the actions of Nature. When man is perfected, his actions are greater than that of Hashem, as the Talmud relates on the verse "Your Hands establish your sanctuary"
Circumvent. This describes Jacob's tricky behavior. The relevance here would be that when we learn to keep mitzvot intelligently, we earn blessings. Jacob's trickiness is intelligence like Adam.

רש"י על דברים ז׳:י״ב:א׳

והיה עקב תשמעון. אִם הַמִּצְווֹת קַלּוֹת שֶׁאָדָם דָּשׁ בַּעֲקֵבָיו תשמעון.

Rashi on Deuteronomy 7:12:1

והיה עקב תשמעון AND THE CONSEQUENCE WILL BE, IF YE HEARKEN (The Hebrew text may be taken to signify if you will hear the heel, עקב) — If, even the lighter commands which a person usually treads on with his heels (i.e. which a person is inclined to treat lightly), ye will hearken to,

בראשית כ״ו:ד׳-ה׳

(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׃...

Genesis 26:4-5

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— inasmuch as Abraham obeyed Me and kept My charge: My commandments, My laws, and My teachings.”

בראשית ג׳:ט״ו

(טו) וְאֵיבָ֣ה ׀ אָשִׁ֗ית בֵּֽינְךָ֙ וּבֵ֣ין הָֽאִשָּׁ֔ה וּבֵ֥ין זַרְעֲךָ֖ וּבֵ֣ין זַרְעָ֑הּ ה֚וּא יְשׁוּפְךָ֣ רֹ֔אשׁ וְאַתָּ֖ה תְּשׁוּפֶ֥נּוּ עָקֵֽב׃ {ס}

Genesis 3:15

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.”

בראשית כ״ה:כ״ו

וְאַֽחֲרֵי־כֵ֞ן יָצָ֣א אָחִ֗יו וְיָד֤וֹ אֹחֶ֙זֶת֙ בַּעֲקֵ֣ב עֵשָׂ֔ו וַיִּקְרָ֥א שְׁמ֖וֹ יַעֲקֹ֑ב וְיִצְחָ֛ק בֶּן־שִׁשִּׁ֥ים שָׁנָ֖ה בְּלֶ֥דֶת אֹתָֽם׃

Genesis 25:26

Then his brother emerged, holding on to the heel of Esau; so they named him Jacob. Isaac was sixty years old when they were born.

בראשית כ״ז:ל״ו

וַיֹּ֡אמֶר הֲכִי֩ קָרָ֨א שְׁמ֜וֹ יַעֲקֹ֗ב וַֽיַּעְקְבֵ֙נִי֙ זֶ֣ה פַעֲמַ֔יִם אֶת־בְּכֹרָתִ֣י לָקָ֔ח וְהִנֵּ֥ה עַתָּ֖ה לָקַ֣ח בִּרְכָתִ֑י וַיֹּאמַ֕ר הֲלֹא־אָצַ֥לְתָּ לִּ֖י בְּרָכָֽה׃

Genesis 27:36

[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?”

תלמוד ירושלמי קידושין ד׳:י״ב:א׳

משנה: מָצִינוּ שֶׁעָשָׂה אַבְרָהָם אָבִינוּ אֶת כָּל־הַתּוֹרָה כֻּלָּהּ עַד שֶׁלֹּא נִיתְּנָה שֶׁנֶּאֱמַר עֵקֶב אֲשֶׁר שָׁמַע אַבְרָהָם בְּקוֹלִי וַיִּשְׁמוֹר מִשְׁמַרְתִּי מִצְוֹתַי חֻקּוֹתַי וְתוֹרוֹתָי.

Jerusalem Talmud Kiddushin 4:12:1

MISHNAH: We find that our father Abraham kept the entire Torah before it was given, as it is said: “As a reward because Abraham listened to My voice and kept My watch, My commandments, My laws, and My teachings.”

בראשית רבתי, פרשת בראשית פ״ו

(בראשית ג, טו) הוא ישופך ראש. בשעה שעוסקים בתורה שכתוב בה מעולם נסכתי מראש (משלי ח' כ"ג) הנחש מתבטל מן העולם, וכה"א אם בחקותי תלכו וגו' והשבתי חיה רעה וגו' (ויקרא כ"ו ג' ו') זו נחש. ואתה תשופנו, תשופנו בשעה שישליך ד"ת אחר העקב, כד"א עון עקבי יסבני(תהלים מ"ט ו'), אותה שעה הנחש משתלח.

Bereshit Rabbati, Parashat Bereshit 86

"(Genesis 3:15) 'He shall crush your head.' When they engage in Torah study, which is written as 'I have been established from eternity, from the beginning' (Proverbs 8:23), the serpent is nullified from the world. And similarly, it is stated, 'If you walk in My statutes, etc., I will remove wild beasts, etc.' (Leviticus 26:3,6), this refers to the serpent. 'And you shall bruise his heel,' it means that when someone casts aside words of Torah, as it is said, 'The iniquity of my heels surrounds me' (Psalms 49:6), at that time the serpent is unleashed.

עבודה זרה י״ז ב:י״ד

אתיוהו לרבי חנינא בן תרדיון אמרו ליה אמאי קא עסקת באורייתא אמר להו כאשר צוני ה' אלהי מיד גזרו עליו לשריפה ועל אשתו להריגה ועל בתו לישב בקובה של זונות עליו לשריפה שהיה

Avodah Zarah 17b:14

The Romans brought Rabbi Ḥanina ben Teradyon for judgment, and they said to him: Why did you occupy yourself with the Torah? Rabbi Ḥanina ben Teradyon said to them, citing a verse: “As the Lord my God commanded me” (Deuteronomy 4:5). They immediately sentenced him to death by means of burning, and they sentenced his wife to execution by decapitation, and his daughter was condemned to sit in a brothel [kubba shel zonot]. The Gemara explains the Divine decree that he should receive this punishment: He was sentenced to death by burning, as he would

עבודה זרה י״ח א:ד׳

ועל בתו לישב בקובה של זונות דאמר ר' יוחנן פעם אחת היתה בתו מהלכת לפני גדולי רומי אמרו כמה נאות פסיעותיה של ריבה זו מיד דקדקה בפסיעותיה והיינו דאמר ר' שמעון בן לקיש מאי דכתיב (תהלים מט, ו) עון עקבי יסבני עונות שאדם דש בעקביו בעולם הזה מסובין לו ליום הדין

Avodah Zarah 18a:4

The Gemara asks: And why was his daughter condemned to sit in a brothel? As Rabbi Yoḥanan says: Once, the daughter of Rabbi Ḥanina ben Teradyon was walking before the nobles of Rome, and they said to each other: How pleasant are the steps of this young woman. Upon hearing this, she immediately took care to keep walking in such a fashion that her steps would continue to be pleasing to them. And this is the same as that which Rabbi Shimon ben Lakish says: What is the meaning of that which is written: “The iniquity of my heel encircles me” (Psalms 49:6)? It means that the sins that a person tramples with one’s heel in this world, i.e., dismisses and pays no attention to them as they seem to lack importance, e.g., the way that one walks, come and encircle him on the Day of Judgment.

ספר הזהר, תולדות ד׳:כ״ה

אָמַר רִבִּי יִצְחָק, כְּתִיב, (בראשית כ״ה:כ״ב) וַיִּתְרֹצֲצוּ הַבָּנִים בְּקִרֵבָּהּ וַתֹּאמֶר אִם כֵּן לָמָּה זֶה אָנֹכִי וַתֵּלֶךְ לִדְרשׁ אֶת יְיָ, לְאָן אֲתַר אָזְלַת. לְבֵי מִדְרְשָׁא דְּשֵׁם וְעֵבֶר. וַיִּתְרֹצֲצוּ הַבָּנִים בְּקִרְבָּהּ, דְּתַמָּן הֲוָה הַהוּא רָשָׁע דְּעֵשָׂו אֲגַח קְרָבָא בֵּיהּ בְּיַעֲקֹב. וַיִּתְרֹצֲצוּ, אִתְבָּרוּ כְּמָה דְאַמְרִינָן, רָצַץ אֶת מוֹחוֹ. אִתְבָּרוּ דָּא עִם דָּא וְאִתְפְּלָגוּ. תָּא חֲזֵי, דָּא סִטְרָא דְּרוֹכֵב נָחָשׁ, וְדָא סִטְרָא דְּרוֹכֵב עַל כָּרְסְיָא שְׁלֵימָתָא קַדִּישָׁא בְּסִטְרָא דְּשִׁמְשָׁא, לְשַׁמָּשָׁא בְּסִיהֲרָא.

Zohar, Toldot 4:25

Rabbi Yitzchak said, It is written, "And the children struggled together within her; and she said, 'if it be so, why am I thus?' And she went to inquire of Hashem" (Gen. 25:22). Where did she go? To the academy of Shem and Ever. "the children struggled together within her," because the wicked Esau was warring against Jacob there. The term 'struggle' (Heb. וַיִּתְרֹצֲצוּ) is similar to the expression 'to break' (Heb. רָצַץ) one's head, for they struggled and were divided. Come and behold, Esau was of the side of he who rides the serpent, (Samael) while JACOB was of the side who rides the perfect Holy Throne, of the side of the sun, that is united with the moon.

ספר הזהר, תולדות ד׳:כ״ו

וְתָא חֲזֵי, בְּגִין דְּאִתְמְשַׁךְ עֵשָׂו אֲבַתְרִיהּ דְּהַהוּא נָחָשׁ, אָזִיל עִמֵּיהּ יַעֲקֹב בְּעֲקִימָא, כְּנָחָשׁ דְּאִיהוּ חַכִּים, וְאִיהוּ אָזִיל בְּעֲקִימוּ, כְּמָה דְאַתְּ אָמֵר, (בראשית ג׳:א׳) וְהַנָּחָשׁ הָיָה עָרוֹם וְגו', חַכִּים. וְעוֹבָדוֹי דְיַעֲקֹב לְגַבֵּיהּ הֲווּ לֵיהּ כְּנָחָשׁ, וְהָכִי אִצְטְרִיךְ לֵיהּ, בְּגִין לְאַמְשָׁכָא לֵיהּ לְעֵשָׂו בַּתְרֵיהּ דְּהַהוּא נָחָשׁ, וְיִתְפְּרַשׁ מִנֵּיהּ, וְלָא יְהֵא לֵיהּ חוּלָקָא עִמֵּיהּ בְּעַלְמָא דֵין וּבְעַלְמָא דְאָתֵי. וְתָנִינָן, בָּא לְהָרְגְּךָ, אַקְדִּים אַנְתְּ וְקַטְלֵיהּ. כְּתִיב, בַּבֶּטֶן עָקַב אֶת אָחִיו דְּאַשְׁרֵי לֵיהּ לְתַתָּא, בְּהַהוּא עָקֵב, הֲדָא הוּא דִכְתִיב, (בראשית כח) וְיָדוֹ אוֹחֶזֶת בַּעֲקֵב עֵשָׂו, דְּשַׁוֵּי יְדוֹי עַל הַהוּא עָקֵב לְאִכַּפְיָא לֵיהּ.

Zohar, Toldot 4:26

Come and behold, since Esau followed on the serpent, Jacob dealt with him slyly, as the serpent was cunning and had crooked ways. As it is written, "the serpent was craftier" (Gen. 3:1), which means that he was cunning (and sly). What Jacob did with Esau was serpent-like. This was as it ought to have been; by making Esau go after that serpent, so that he would be separated from Jacob, and thus share nothing with him in this world or in the World to Come. Thus we learn, "he who comes to kill you, hasten to kill him first." It is written, "in the womb he took his brother" (Hoshea 12:4), which means that he lowered him down by the heel. This is the meaning of, "and his hand took hold of Esau's heel" (Gen. 25:26), for he put his hands on the heel to subjugate him.

The below sources talk about Adam's heels. If beauty here is a metaphor for the mind, and heels are a metaphor for action, the stories are understandable.

בבא בתרא נ״ח א:ג׳

רַבִּי בְּנָאָה הֲוָה קָא מְצַיֵּין מְעָרָתָא. כִּי מְטָא לִמְעָרְתָּא דְאַבְרָהָם, אַשְׁכְּחֵיהּ לֶאֱלִיעֶזֶר עֶבֶד אַבְרָהָם דְּקָאֵי קַמֵּי בָּבָא. אֲמַר לֵיהּ: מַאי קָא עָבֵיד אַבְרָהָם? אֲמַר לֵיהּ: גָּאנֵי בְּכַנְפַהּ דְּשָׂרָה, וְקָא מְעַיְּינָא לֵיהּ בְּרֵישֵׁיהּ.

Bava Batra 58a:3

§ Having mentioned Rabbi Bena’a, the Gemara relates an incident in which he was involved. Rabbi Bena’a was marking burial caves for the purpose of helping to prevent the contracting of ritual impurity. When he arrived at the cave of Abraham, i.e., the Cave of Machpelah, he encountered Eliezer, the servant of Abraham, who was standing before the entrance. Rabbi Bena’a said to him: What is Abraham doing at this moment? Eliezer said to him: He is lying in the arms of Sarah, and she is examining his head.

בבא בתרא נ״ח א:ד׳

אֲמַר לֵיהּ, זִיל אֵימָא לֵיהּ: בְּנָאָה קָאֵי אַבָּבָא. אֲמַר לֵיהּ: לֵיעוּל – מִידָּע יְדִיעַ דְּיֵצֶר בְּהַאי עָלְמָא לֵיכָּא. עָיֵיל, עַיֵּין וּנְפַק.

Bava Batra 58a:4

Rabbi Bena’a said to him: Go tell him that Bena’a is standing at the entrance, so that he should assume an appropriate position to receive a visitor. Eliezer said to him: Let him, i.e., Rabbi Bena’a, enter, since it is known that there is no evil inclination in this higher world, so it is not inappropriate for Rabbi Bena’a to see Abraham and Sarah in this position. He entered, examined the cave in order to measure it, and exited.

בבא בתרא נ״ח א:ה׳

כִּי מְטָא לִמְעָרְתָּא דְּאָדָם הָרִאשׁוֹן, יָצְתָה בַּת קוֹל וְאָמְרָה: ״נִסְתַּכַּלְתָּ בִּדְמוּת דְּיוֹקְנִי, בִּדְיוֹקְנִי עַצְמָהּ אַל תִּסְתַּכֵּל״. ״הָא בָּעֵינָא לְצַיּוֹנֵי מְעָרְתָּא!״ ״כְּמִדַּת הַחִיצוֹנָה כָּךְ מִדַּת הַפְּנִימִית. וּלְמַאן דְּאָמַר שְׁנֵי בָתִּים זוֹ לְמַעְלָה מִזּוֹ – כְּמִדַּת עֶלְיוֹנָה כָּךְ מִדַּת הַתַּחְתּוֹנָה״.

Bava Batra 58a:5

When he arrived at the cave of Adam the first man, who is buried in the same area, a Divine Voice emerged and said: You gazed upon the likeness of My image, i.e., Abraham, who is similar to the image of Adam the first man. Do not gaze upon My image itself, i.e., Adam the first man, about whom the verse states that he was formed in the image of God (see Genesis 1:27). Rabbi Bena’a said: But I need to mark the cave. The voice said to him: As the measurements of the dimensions of the outer cave where Abraham is buried, so are the measurements of the dimensions of the inner cave, where Adam is buried. The Gemara notes: And according to the one who says that the Cave of Machpelah consists of two chambers, this one above that one, not two adjacent chambers, the voice said: As the measurements of the dimensions of the upper cave where Abraham is buried, so are the measurements of the dimensions of the lower cave. Therefore, there is no need to measure it.

ספר הזהר, תולדות י״ז:קל״ג

אָמַר רַבִּי יוֹסֵי, יָפְיוֹ שֶׁל יַעֲקֹב (היה) שֶׁהוּא יָפְיוֹ שֶׁל אָדָם אֵיךְ אֶפְשָׁר? וַהֲרֵי שָׁנִינוּ, תַּפּוּחַ עֲקֵבוֹ שֶׁל אָדָם הָרִאשׁוֹן מַכְהֶה גַּלְגַּל חַמָּה, וְאִם תֹּאמַר שֶׁכָּךְ הָיָה יַעֲקֹב? אָמַר לוֹ רַבִּי אֶלְעָזָר, וַדַּאי שֶׁכָּךְ הָיָה. בָּרִאשׁוֹנָה טֶרֶם חָטָא אָדָם הָרִאשׁוֹן, לֹא הָיוּ יְכוֹלִים כָּל הַבְּרִיּוֹת לְהִסְתַּכֵּל בְּיָפְיוֹ. כֵּיוָן שֶׁחָטָא, הִשְׁתַּנָּה יָפְיוֹ וְרוּמוֹ הֻנְמַךְ, וְנַעֲשָׂה בֶּן מֵאָה אַמּוֹת. וּבֹא וּרְאֵה, יָפְיוֹ שֶׁל אָדָם הָרִאשׁוֹן הוּא סוֹד, שֶׁהָאֱמוּנָה הָעֶלְיוֹנָה תְּלוּיָה בַּיֹּפִי הַהוּא, וּמִשּׁוּם כָּךְ (תהלים צ) וִיהִי נֹעַם ה' אֱלֹהֵינוּ עָלֵינוּ, וְכָתוּב (שם כז) לַחֲזוֹת בְּנֹעַם ה'. וְזֶהוּ וַדַּאי יָפְיוֹ שֶׁל יַעֲקֹב, וְהַכֹּל הוּא סוֹד עֶלְיוֹן.

Zohar, Toldot 17:133

Rabbi Yosi said, Jacob's beauty was the beauty of Adam. How could this be? We learned that the apple of Adam's heel eclipsed the orb of the sun. Could you say that for Jacob? Rabbi Elazar replied, assuredly before Adam sinned no creature could behold his beauty. But after he sinned, his beauty changed, his stature diminished, and he was a hundred cubits high. Come and behold, Adam's beauty is a mystery on which supernal faith stems. Of this, the scripture says "And let the beauty of Adonai our Elohim be upon us" (Tehilim 90:17). It is also written, "to behold the beauty of Hashem" (Tehilim 27:4). This is, assuredly, the beauty of Jacob. And all is in the supernal mystery.

The double-cave is a metaphor for two levels in the afterlife.

בבא בתרא נ״ח א:ו׳

אָמַר רַבִּי בְּנָאָה: נִסְתַּכַּלְתִּי בִּשְׁנֵי עֲקֵיבָיו, וְדוֹמִים לִשְׁנֵי גַּלְגַּלֵּי חַמָּה. הַכֹּל בִּפְנֵי שָׂרָה – כְּקוֹף בִּפְנֵי אָדָם. שָׂרָה בִּפְנֵי חַוָּה – כְּקוֹף בִּפְנֵי אָדָם. חַוָּה בִּפְנֵי אָדָם – כְּקוֹף בִּפְנֵי אָדָם. אָדָם בִּפְנֵי שְׁכִינָה – כְּקוֹף בִּפְנֵי אָדָם.

Bava Batra 58a:6

Rabbi Bena’a says: I gazed at his, Adam’s, two heels, and they shone so brightly that they are similar to two suns. Along these lines, the Gemara states that all people compared to Sarah are like a monkey compared to a human, as Sarah was exceedingly beautiful; Sarah compared to Eve is like a monkey compared to a human; Eve compared to Adam is like a monkey compared to a human; and Adam compared to the Divine Presence is like a monkey compared to a human.