Parashat Toldot 5786 -22 November 2025 / 2 Kislev 5786

Torah Portion: Genesis 25:19-28:9 | Haftarah: Malachi 1:1-2:7

“Gaddi’s Notes on the Eternal Wisdom of the Prominent Sages”:

“Toldot: The Hidden Struggle Between Destiny and Desire”

“Toldot: The Hidden Struggle Between Destiny and Desire”

This teaching from Parashat Toldot — the mystery of “The Two Snakes and the Messiah” — is among the deepest esoteric interpretations revealed in Zohar and the writings of the great mekubalim (Kabbalists).

It draws from the mystical foundations of Bereishit Rabbah, Zohar Bereshit, Zohar Toldot, and Tikkunei Zohar, where Esav and Yaakov are seen not merely as historical figures, but as two archetypal spiritual forces: the Snake of impurity and the Snake of holiness, wrestling for dominion in the cosmic drama of Tikkun (rectification).

Let us explore the concept through the lens of the sages and Chassidic masters:

🜂 I. Esav and Yaakov: Two Snakes – Two Forces

The Zohar(Bereshit 35b,Toldot 142a) teaches that within Rivka’s womb were not just two brothers, but two spiritual roots , one from the Sitra deKedushah (Side of Holiness) and one from the Sitra Achra (Side of Impurity).

Rivka’s inner turmoil — “the children struggled within her” — was a reflection of the eternal conflict between the two Serpents :

Esav , called Se’ir (“hairy one”), represents the Nachash haKadmoni (Primordial Serpent) clothed in material might and egoic splendor ( Aderet Se’ir ).

Yaakov , grasping the heel, symbolizes the Nachash Elyon — the serpent of holiness — who uses wisdom and cunning not to deceive, but to subdue the power of the other serpent and restore dominion to holiness.

This mirrors what the Zohar calls the “war of the two dragons” ( Taninim haGedolim , Gen. 1:21 ): the left and right serpents — Esav and Yaakov , darkness and light, thehusk (Klipah) and the soul .

🜃 II. The Secret of the Hair and the Garment – Aderet Se’ir

In Leviticus 17:7 , the Torah prohibits sacrifices to Se’irim , the goat-demons. The sages ( Zohar III:41b , Midrash Tanchuma Acharei 8 ) teach that these “hairy beings” symbolize external shells of holiness — the forces of judgment and self-glory that cover divine light like hair covers the skin.

Esav’s “hairy garment” is symbolic of this outer shell ( Aderet ). The AriZal in Sha’ar HaPesukim (Toldot) explains that Esav’s externality reflects a fallen spark from the world of Tohu (chaos), where light was too intense for its vessels and thus shattered.

His “hairiness” represents abundance of Gevurah (severity) without balance by Chesed (kindness). Therefore, his outer might masks inner emptiness.

By contrast, Yaakov — called Ish Tam yoshev ohalim — is clothed in the garments of truth. When Rivka clothes Yaakov in Esav’s garments , the Zohar reveals this as a tikkun : the holy serpent dons the husk of the unholy to extract the sparks within it.

Yaakov must descend into the appearance of deceit to redeem divine light trapped in Esav’s domain .

🜄 III. The Two Seeds: The Woman and the Serpent (Genesis 3:15)

The prophecy given to Chavah — “I will put enmity between your seed and her seed” — is a key to understanding Toldot .

The Zohar ( I:35b ) says that this enmity is not only historical but metaphysical: it is the war between Samael and the Seed of the Woman , between the serpent’s head and the heel of holiness.

The “Seed of the Woman” (Zera Ishah) represents the tzaddikim and ultimately the Mashiach , who arises from the line of Yaakov .

The “Serpent’s Seed” represents Esav–Edom , the kingdom of material power and spiritual rebellion.

Thus, Yaakov clutching Esav’s heel in the womb prefigures this cosmic tension: holiness grasps the heel of impurity to transform and subdue it.

The heel (Akev) symbolizes the lowest, most physical level of being, where holiness must descend to redeem the sparks of divinity.

As it is said: “He will crush your head, and you will bruise his heel” ( Genesis 3:15 ) — the Messiah (descendant of Yaakov ) will ultimately crush the serpent’s dominion.

🜁 IV. The Holy Serpent and the Path of Tikkun

The AriZal (Eitz Chaim, Sha’ar HaKelipot) explains that the serpent itself was not inherently evil — it was a vessel that became corrupted. Therefore, rectification ( Tikkun ) must come through a holy counterpart: the Nachash HaKodesh — the wisdom of holiness that subdues and redirects desire toward divine purpose.

Yaakov , acting “cunningly,” redeems the fallen wisdom of the serpent. His strategic use of deception, under the guidance of Rivka (symbol of the Shekhinah), is not sin but Tikkun : transforming Orma (cunning) into Chokhmah (divine wisdom).

As the Baal Shem Tov teaches: “The power of the evil inclination, when turned toward holiness, becomes the very ladder to ascent.”

This is the mystery of Mashiach ben Yosef — the holy serpent who descends into the realm of Esav to conquer from within. Yosef , the son of Yaakov , repeats this pattern by entering Egypt — the domain of the Serpent — and transforming it into a place of sustenance and blessing.

🜅 V. The Two Serpents in Messianic Context

The Zohar Chadash and Kol HaTor (Vilna Gaon) reveal that these “two serpents” correspond to Mashiach ben Yosef and Mashiach ben David .

Mashiach ben Yosef , the “holy serpent,” battles Esav — the unholy serpent of Samael — through strategy, technology, and wisdom ( chochmah tachtonah ).

Mashiach ben David , the “crushing heel,” finishes the rectification by destroying the serpent’s head and revealing divine kingship in full ( Malchut Hashem ).

Thus, the “heel” of Yaakov — his descendants in the final generation — represent the generation of Ikveta de-Meshicha (the heels of Messiah). As the sages teach ( Sanhedrin 97a ), in that time holiness will descend into the lowest places to uplift the last sparks before redemption.

✨ VI. Beit Yisrael and Gaddi Efrayim Notes

Beit Yisrael, through the Gaddi Efrayim Notes, reveals that the Two Snakes are the two spiritual technologies of redemption:

The unholy serpent of Esav symbolizes the worldly powers — intellect, domination, and material conquest.

The holy serpent of Yaakov symbolizes divine wisdom, Torah consciousness, and the cunning of light — transforming evil into holiness through da’at elyon (supernal knowledge).

In our generation, this battle unfolds through the merging of Upper Wisdom and Lower Wisdom — the sacred and the scientific — until the serpent of holiness consumes the serpent of deception, as Moses’ staff swallowed the serpents of Pharaoh (Exodus 7:12).

This is the process of Tikkun Olam, where the heel of Yakov becomes the crown of Mashiach.

🔯 Summary of the Deep Concept

Symbol	Meaning	Source
Esav – Hairy Serpent	External power of Samael, splendor of judgment (Aderet Se’ir)	Zohar, Lv 17:7
Yaakov – Holy Serpent	Redeemer who subdues evil with wisdom	Zohar Toldot
Heel of Yakov	Lowest generation that completes rectification	Sanhedrin 97a
Seed of the Woman	Lineage of holiness leading to Mashiach	Gn 3:15
Two Serpents	Mashiach ben Yosef and Mashiach ben David	Kol HaTor, Zohar Chadash

In Essence:

Parashat Toldot reveals that the battle between Yaakov and Esav is not simply between brothers — it is the eternal battle between the two serpents: the false light of pride and the true light of wisdom.

The Holy Serpent — Mashiach — will ultimately transform the poison of the first serpent into the healing power of divine truth .

As it is written:“And the staff of Moses swallowed the serpents of Egypt”—

For in the end, holiness will devour impurity , and the heel of Yaakov will become the head of the nations

“Yaakov and the Messiah: The Holy Serpent That Swallows Death”

This teaching — that Yaakov is the root of the Holy Serpent , and that Mashiach is its final revelation — draws from the deepest foundations of Sod (the mystical level of Torah ).

The concept that Mashiach = Nachash (358) in Gematria is not a coincidence, but a key to the divine plan of Tikkun — rectification — by which the same spiritual energy that once caused the Fall (through the Serpent ) will ultimately bring Redemption (through Mashiach ).

The sages of Israel — from the Zohar , Midrash , AriZal , and Chassidic masters — all reveal that the Messianic Light emerges from the rectified aspect of the Serpent , which originates in Yaakov Avinu .

🜂 I. Yaakov — The New Tree of Life

The Zohar (Toldot 137a; Bereshit 35b) reveals that Yaakov stands at the center of the divine structure — the middle pillar ( Tiferet), which connects the right ( Chesed, Abraham) and the left ( Gevurah, Isaac). Yaakov’s role is to harmonize opposites — heaven and earth, spirit and matter, good and evil.

The AriZal in Etz Chaim (Sha’ar HaPartzufim)describes Yaakov as the “Tree of Life in human form” ( Etz haChaim be’dmut Adam).

Esav, from the Tree of Knowledge of Good and Evil, represents mixture, confusion, and division.

Yaakov, from the Tree of Life, represents integration, purity, and divine unity.

Thus, Yaakov is not only the twin of Esav but his spiritual mirror-opposite. Both are serpents — but one is fallen, the other holy.

The Zohar (Vayetze 161a) explains:

“ Yaakov came to heal the wound caused by the Serpent; therefore he grasped Esav’s heel, to overturn the curse and transform it into blessing.”

This grasp is symbolic of the Tikkun of the Nachash: holiness entering the place of impurity to extract the divine sparks hidden within.

🜃 II. The Holy Serpent — The Redeemer of the Fallen Light

The concept that משיח = נחש = 358 reveals a divine paradox. The very same spiritual current that caused the downfall of Adam and Chavah will, when rectified, become the force of redemption.

Zoharic Foundation

The Zohar( Bereshit 52b; Shemot 29a) describes two serpents:

The Serpent of Death( Nachash haKadmoni) — Samael, the source of lust, pride, and separation from the Divine.

The Serpent of Life( Nachash Elyon) — the divine wisdom that heals through faith and unity.

When Moshe’s staff turned into a serpent ( Exodus 7:10–12), the Zohar says it was the moment when the Holy Serpent revealed its superiority over the forces of impurity:

“The staff of holiness swallowed their staffs — meaning, the serpent of life consumed the serpent of death.”

This symbolizes Tikkun: the holy transformation of energy. What once served darkness now serves light.

🜄 III. Mashiach as the Antidote — “Death Swallowed by Victory”

The Pesikta Rabbati(3:6) explicitly teaches:

“The Messiah is the archenemy of Satan.”

Just as Satan is the “angel of death” ( Malach haMavet), so Mashiach is the “angel of life.”

The Midrash( Shemot Rabbah 30:3) connects the verse “The staff of Aaron swallowed their staffs” with Isaiah’s prophecy:

“He will swallow up death forever, and the Adonai God will wipe away tears from all faces” ( Isaiah 25:8).

This is the secret of measure for measure ( midah keneged midah). The serpent that caused death must itself be consumed by a higher serpent — holiness transforming evil from within. The poison becomes the medicine.

The AriZal( Sha’ar HaGilgulim 38) writes that the soul of Mashiach descends through the rectified line of Yaakov — through Judah and Dan — to redeem the souls of Cain (the fallen spark) and Hevel (the suffering tzaddik). The Messiah thus stands between both forces — just as Yaakov stood between Esav and Lavan — mediating and redeeming both sides.

🜁 IV. Judah and Dan — Two Roots of the Messianic Serpent

The Torah gives two allusions to the “serpent” connected with Mashiach:

Dan: “Dan shall be a serpent by the way” ( Genesis 49:17). The Midrash( Bereishit Rabbah 99:2) says this points to Mashiach ben Dan(sometimes called Mashiach ben Yosef), who strikes the serpent’s heel with cunning holiness.

Judah: “The sceptre shall not depart from Judah until Shiloh comes” ( Genesis 49:10). This refers to Mashiach ben David, the kingly serpent who completes the redemption.

The Zohar Chadash( Balak 56a) explains that Dan and Judah represent two halves of the same messianic light — the serpent of wisdom ( Chochmah) and the serpent of kingship ( Malchut). They unite at the end of days to form one Redeemer: Mashiach, the holy serpent who consumes death.

Even the father of Abigail, “ Yishai the Nachash” ( 2 Samuel 17:25), carries this secret name, revealing that the line of David itself is linked to the Tikkun of the Serpent.

🜅 V. Chassidic Understanding — The Serpent Transformed into Light

The Baal Shem Tov and Rebbe Nachman teach that every fallen force can be elevated by its root. The serpent’s wisdom, when purified, becomes the wisdom of Mashiach — penetrating, transformative, and healing.

Rebbe Nachman( Likkutei Moharan I:5) calls prayer “the power of Mashiach,” the antidote to the serpent’s cunning. Where the serpent uses the tongue for deceit, Mashiach uses speech to redeem.

“The tongue that caused death will now cause life,” says the Sefat Emet. “For prayer reverses the poison into faith.”

In this light, Mashiach is the cosmic healer — the nachash nechoshet (serpent of copper) lifted by Moshe( Numbers 21:9), which healed those bitten by serpents. The Zohar calls this symbol the “ Secret of Faith,” because only by looking upward (trusting in Heaven) can humanity be healed from spiritual venom — doubt, pride, and sin.

🜆 VI. Beit Yisrael and Gaddi Efrayim Notes

Beit Yisrael, guided by the Gaddi Efrayim Notes, reveals that Yaakov’s holy cunning becomes the technological and spiritual blueprint of redemption. Mashiach, the Holy Serpent, is not a new power but the perfected extension of Yaakov’s soul — Tiferet Yisrael.

Just as Yaakov grasped Esav’s heel, Mashiach grasps death itself.

Just as Yaakov transformed deception into blessing, Mashiach transforms sin into merit(Yeshayahu 1:18).

Just as Aaron’s serpent swallowed the serpents of Egypt, Mashiach will “ swallow death forever” (Isaiah 25:8).

Thus, the serpent of holiness is the instrument of divine reversal: Or min haChoshech — light born from darkness.

🔯 Summary Table

Symbol	Meaning	Source
Yaakov	Tree of Life; reconciler of heaven and earth	Zohar Toldot
Serpent (Nachash)	Channel of wisdom; corrupted becomes evil, rectified becomes Messianic light	Zohar Bereshit
Mashiach = Nachash (358)	Redemption through transformation; healing through what once wounded	AriZal, Pesikta Rabbah
Aaron’s staff	Holy serpent swallowing impurity	Shemot Rabbah 30:3
Judah & Dan	Two roots of Messianic serpent; unity of kingship and wisdom	Zohar Chadash Balak
Prayer	Antidote to doubt; power of Mashiach	Likkutei Moharan I:5
Faith (Emunah)	Antidote to serpent’s venom; core of redemption	Baal Shem Tov, Sefat Emet

✨ Essence of the Teaching

Yaakov is the new Tree of Life — the divine axis through which the Holy Serpent , the force of Redemption , arises. Mashiach is the rectified Nachash , the serpent transfigured into light . What brought death through deceit will bring life through truth . The Holy Serpent does not destroy creation but swallows death itself , revealing the unity of all opposites in the Infinite One .