After Reuben did teshuvah, he merited bringing the duda’im [jasmine flowers], (Gen. 30:14) which resulted in the birth of Issachar, who is from the good side of Cain the firstborn. Eve said when Cain was born, "I have acquired a man with G‑d," (Gen. 4:1) which is actually an allusion [to Cain’s rectification through Issachar], since both Eve and Leah were from the level of bina, which as we know is called Imma Ila’a [the supernal maternal aspect].

Both Rachel and Leah are from Eve, who is of dual nature.

Both Rachel and Leah are from Eve, who is of dual nature.1 Each one embodies a different mode: Leah the upper/bina aspect, Rachel the lower/malchut aspect. (Eitz Chaim, Shaar Rachel V'Leah) Together they form the complete archetype, feminine principle Above.

Jasmine (or mandrake, according to other translators) was known to have birth powers. Rachel had not as of yet had children and was willing to sacrifice a night of the privilege of being with Jacob in order to increase her chances of conception. Leah waited for Jacob to come from the field and ushered him into her tent.

The firstborn takes a double portion in the inheritance because spiritually he actually participates in the conception of the following children. (Likutei Torah, Eitz Chaim) This is why specifically Reuben the firstborn brought the duda’im. The duda’im transfer from Leah to Rachel embodies a shift in the supernal realms of blossoming powers from upper to lower rungs.

Issachar is the result of this.2 Let us examine some of his level in order to then look back at these his roots and understand their inner mechanics.

The tribe of Levi has no portion in the land - G‑d is their portion. (Num. 18:20) They are to be busy with spiritual pursuits alone. The Rambam teaches that every person has the option to be like Levi (Mishna Torah, Hilchot Shemita Ve-Yovel 13:13) by letting go of worldly endeavors and fully focusing on Above.

Issachar is the pioneer who paved the path for all who wish to do so. Because he was born to this world and has his portion in it, and nevertheless restrains himself from making it a focus, he is continuously connected Above and is extra bound to the world-to-come. According to the Ohr Hachayim, his name means 'yaish-sechar [there is reward]' - in the world-to-come. The Ari'Zl tells that the catalyst of his birth is the teshuvah of Reuben. The Zohar states that teshuvah comes from bina, the eighth sefira that lies a rung above known reality.

His name has two S/sin's - one is pronounced, the other is not.3 The form of this letter is three heads sitting on a base. The three headed S/sin corresponds to the three heads of keter, corresponding to the crowns of Priesthood, Kingship, and Torah. One can only be born into the first two, whereas Torah can be acquired be anyone. It also includes the other two.4

The teshuvah of Reuben, who had all three, empowers Issachar to be a vessel for some degree of their manifestation - both the three heads of this world and the next.

...the complete tikun of Cain came through Issachar...

Thus, there is a hint to the fact that the complete tikun of Cain came through Issachar, who was born as a result of an 'acquisition' [just as Cain is so called]. For Leah bought the right to be with Jacob from Rachel as a result of the duda’im, as it says, "Therefore he shall lie with you tonight in return for your son’s duda’im." (Gen. 30:15)

"Blessed is Abram to E-L the Highest One - who acquires Heaven and earth..." (Gen. 14:22) We learn from this that Abram is one of G‑d's five special acquisitions in His universe. (Pirkie Avot)

G‑d, as if, lost ownership of His world when He made it and separated it from himself and He repossessed His world through Abraham. Eve lost Divinity by her mistake and repossessed G‑dliness by giving birth. This reveals a great depth of how awesome the Cain root is - through it special relationship is re-established between man and G‑d - in the closest, most inter-personal manner.

This sheds light on the source of Cain’s mistake. His name also comes from kinah [jealousy]. A person is only jealous because they see somewhere else something that they want because they feel that it really does belongs to them. A piece of Divinity fell away from them through Adam’s mistake and is now found somewhere else.

G‑d has a much greater degree of favor to show Cain. For this reason he has to undergo great obstacles to attain it. Cain the firstborn is supposed to get a double portion. (Deut. 21:17) Cain was jealous of Abel’s receiving the Divine favor (Gen. 4:5) and also that his brother had an extra wife. (Breishit Raba 22:7) He sees not just that Abel has twice as much as him, but that the additional wife is actually his soulmate.5

Reuben comes from the Cain root and fixes it. He was born into the most exalted acquisitions. When he lost what was his, he was not jealous. As mentioned, 're’u ben' - see the distinction between him and Esau, who was so jealous that he was ready to kill, (Gen. 27:41) just as Cain did at the beginning of days.

At first, Leah was upset at Rachel’s request for the duda’im. "To almost take away my husband - and to also take my son’s duda’im?!" (Gen. 30:15) This is understood in light of the story of Jacob’s matrimony. He wanted Rachel and made a deal with Laban to work for her seven years. At the end of the term, Laban pulled a switch on him and gave him Leah instead. Even though Jacob and Rachel set signs between them to avoid this, Rachel gave over the signs to Leah at the final moment to prevent her from being embarrassed. (Pesicha, Eicha Rabati 24) This act of giving away what was hers rectified Cain’s taking what was not technically his.6 Rachel ended up not losing Jacob, for he worked another seven years and also married her.7

...Leah was said to be destined to marry Esau.

This is all understood more deeply in light of the fact that Leah was said to be destined to marry Esau. She found out that he was wicked and cried to be saved from this.8 G‑d heard her prayers and gave her to Jacob instead. This explains why her firstborn Reuben specifically comes to fix the Esau/Cain root.

After Eve’s re-acquiring Divinity was disrupted by Cain’s sins, the Eve root worked through Rachel and Leah. They fixed it by Rachel acquiring from Leah, resulting in Issachar/world-to-come connection. The chasing away of the highest levels of G‑dliness caused by the original sin was bought and brought back into the world through this whole scenario.

So Issachar, the fifth portion [Leah’s fifth son] from the side of good, was born. Since he is from the level of nefesh [which is] called Asiya, there was [in him] a connection to kelipot and zuhama [dirt] of the snake [who attacks the heel. (Gen. 3:15)] Therefore, Esau, who is called snake, had a hold on him, and he is called the "heel of Esau" (Gen. 25:26) - since he is from Asiyah, which is called the heel [it being the lowest of realms].

Leah’s seven children correspond to the seven lower sefirot in order, so Issachar aligns with hod. In the body, it expresses as the left leg. This is the place that Satan damaged when he lost the wrestling match with Jacob. (Zohar, Breishet) It caused him to limp.

Reuben is the catalyst for hod/Issachar’s birth. He corresponds to chesed. These sefirot find inter-linkage in Aaron, who is the fifth/hod representative of the seven shepherds, (Zohar III Emor) and a kohen is called "a man of chesed ". (Zohar, Vayechi) The Chanukah/hod miracle happened through kohanim.

Issachar acquired the crown of Torah. As mentioned, the crown of Torah includes the other two - Priesthood and Kingship. Issachar/hod is the forerunner of Chanukah. He restores to the world the special inner, hidden light of Torah. This snatches back and retrieves the levels stolen by Satan from Jacob in their battle. Through Issachar’s mesirot nefesh for Torah, his descendents were able to give their lives for the Torah and draw a new revelation of its light.9 The Temple was restored and the kohanim shone their brightest and even temporarily took hold of the kingship.

We see now a little of why the Ari'Zl. here mentions that Issachar is the fifth son.

Jacob snatched them from Esau, in the secret of "His hand was holding onto the heel of Esau," (Gen. 25:26) and Issachar was born from this level of nefesh. Much later in time, Rabbi Akiva ben Yosef, whose name has within it aikev, was born from this level of nefesh. As we alluded to in previous discussions, based upon Midrash Rut of the Zohar, that Issachar is [from] Rabbi Akiva.10

This hold of Esau caused the friction in the story around Issachar’s birth. It also caused Rabbi Akiva to not learn during the first forty years of his life.

As mentioned, Jacob comes from the aikev [heel], because his glory primarily comes out at the tail, heel/end of days. Issachar/yesh-schar is a special sneak-peak preview of this level here and now.11 Therefore he comes specifically from Jacob’s snatching Esau’s heel, capturing the prime Tohu lights in Esau that are to shine out at history’s conclusion. The 'snatching' is the aspect of the sneak-peak.

Rabbi Akiva furthered this tikun and built a legion of 24,000 students

Rabbi Akiva furthered this tikun and built a legion of 24,000 students who drew from this deluxe level. It was such a high category that it could not remain in the world as is and they died an untimely death.12 But their having had a brief hey-day drawing from this premium category brought it a step closer to the world and paved the way all the more for it to eventually fully manifest at the end of days. He started again and rebuilt from five super-students - who parallel the five special possessions of G‑d in His world.13 Through them the whole world will become the special possession of the One Above in the final redemption.

[Translation and commentary by Perets Auerbach.]