(זְבוּלֻן לְחוֹף יַמִּים יִשְׁכֹּן וְהוּא לְחוֹף אֳנִיּוֹת וְיַרְכָתוֹ עַל צִידֹן (בראשית מט' יג

"Zevulun will dwell on the coast of the seas; he [will be] at the harbor of the ships, and his boundary will be at Tzidon” (Bereishis 49:13)

"היה מצוי תדיר על חוף אניות, במקום הנמל, שאניות מביאות שם פרקמטיא, שהיה זבולן עוסק בפרקמטיא, וממציא מזון לשבט יששכר והם עוסקים בתורה, הוא שאמר משה (דברים לג יח) שמח זבולן בצאתך ויששכר באהליך, זבולן יוצא בפרקמטיא ויששכר עוסק בתורה באהלים" (רש''י שם)

“He (Zevulun) will be constantly found...where ships bring merchandise; For Zevulun would engage in commerce and provide food for the Tribe of Yissachar, while they (the tribe of Yissachar) would engage in Torah study. This is what Moshe said (in his blessing to the tribes of Yisrael) “Rejoice, Zevulun, in your going forth and Yissachar in your tents” (Devarim 33:18): Zevulun would go out and engage in commerce and Yissachar would engage in Torah study in the tents”
- (Rashi, ibid. based on Midrash Rabbah 99:9 & Midrash Tanchuma Vayechi 11)

In the brother tribes of Yissachar and Zevulun we find the ultimate partnership in this world; the union of the material and spiritual, working hand in hand, each serving and elevating the other. This was the partnership G-d had originally intended for Adam HaRishon and the original Snake, for Adam was to encompass the spiritual light of creation, reflecting the Creator, and the gifted snake was to be his servant in innovating and elevating the physical world. Had the original sin not occurred, ChaZaL tell us that, like by Adam, the snake would be our most useful servant, even to this day (see Sanhedrin 59b).

It was this partnership that should have been Kayin and Hevel’s, and subsequently could have been Avraham and Lot’s, Yishmael and Yitzchak’s; even Eisav and Yaakov could have achieved this intended goal. However, each time, one side of the fellowship failed to realize this ultimate union, and the world’s rectification kept being set back.

Finally, within Yaakov’s children, Yissachar and Zevulun, a great rectification was achieved in finally bridging the material and spiritual facets of creation. While Yissachar was supported physically by Zevulun, Zevulun benefitted from the light of Torah that otherwise he would not have been attained. The Malbim teaches (in his commentary to Bereishis 27) that ultimately, on a grander scale, within the Jewish people, the tribe of Levi embodied the qualities of Yissachar and the rest of the tribes embodied the qualities of Zevulun. And, ultimately, what Yissachar was to Zevulun, and the tribe of Levi to Yisrael, the Jewish people are relatively meant to be the rest of the nations of the world. This dynamic would fulfill the purpose of creation. (In the future when this is realized the nations will attempt to claim how they materially assisted the Jewish people in fulfillment of this relationship; see Avodah Zarah 2b)

Considering how essential this dynamic is to creation’s purpose, it therefore makes sense that there would be two Mashiachs, Mashiach ben Yosef and Mashiach ben David who would manifest the two sides of the equation, working together to bring unity and perfection to creation. What Zevulun is to Yissachar, Mashiach ben Yosef is to Mashiach ben David and vice versa. Let’s take a step back for a moment and appreciate the full picture that all these puzzle pieces come to create:

G-d created the world with a dichotomy, two contrasting forces which need to achieve union in order to ultimately reveal G-d’s unity. One way to put it: the material & the spiritual, the body & soul, of creation, reflecting G-d’s relationship to the world. Out if this we have the concept of “Mashpiah” and “Mikabel”, “Giver/Bestower”, and “Receiver”. Each one gives purpose to the other, in a “loop-like” interdependent relationship. The Giver has no purpose for being if not to resemble The Creator in giving to another, and the Receiver has nothing without someone to bestow good upon them. But by allowing for the concept of receiving from the Giver, the Receiver gives purpose to the Giver and becomes himself a Giver, in a way, from which the Giver benefits and thus becomes a Receiver, in a way. And thus the relationship feeds of itself, Giver and Receiver in a constant exchange of roles. Ultimately we could call this “unity”.

In Kabbalistic terms, this is to the interplay between the sefiros of Yesod (Giver) and Malchus (Receiver). Yesod imparts from above to Malchus, Malchus reciprocates from below to Yesod. This also relates to the relationship between Yesod and Malchus expressed by Zevulun and Yissachar. (Because, as we said above, this relationship constantly exchanges roles, Zevulun could be viewed from one perspective as Malchus and from another Yesod; and similarly Yissachar. In this approach I am focusing on Zevulun as Yesod bestowing upon Yissachar in Malchus)

Yosef HaTzaddik went down to Egypt and was elevated to viceroy to be in a position to materially support the rest of the family of Yisrael (Bereishis 45:5, 47:12). But the mere physical existence and success of the Jewish people, without the spiritual, was not the full intended goal. Therefore, keeping the ultimate goal in mind Yaakov “sent Yehudah before him to Yosef, to instruct ahead of him in Goshen” and then “they came to the land of Goshen” (Bereishis 46:28):
What did Yehudah establish as his part in the partnership between the “Yosef- Yehudah/ Material and Spiritual” aspects of the nation, once Yosef had the material ones in place? He established “a house of Torah study from which instruction would go forth” (Rashi ibid. based on Midrash Tanchuma 11 & Bereishis Rabbah 95:3). Yaakov, with the ultimate unity in mind, laid the foundation within the Jewish people for what would become the Yissachar/Zevulun partnership.

Codified in Jewish law, we find in the Shulchan Aruch (Yoreh De’ah 246:1) that “one who is unable to learn himself should support others in learning Torah”, to which the Ramah adds “and it is considered as if he himself had learned. Furthermore, two people can stipulate a partnership in which one learns Torah exclusively and the other provides for his needs, and the merit of the learning is equally divided between them”. The Vilna Gaon, in his commentary to these words points out that this expresses the relationship between Yissachar and Zevulun as taught by ChaZaL (see sources quoted above).

This partnership described between Yissachar and Zevulun is not merely an optional one, but at times is actually what Divine providence determines as the necessary approach. In his work on various Aggados (esoteric Talmudic teachings, under the title “Peirush Al Kamah Aggados”) the Vilna Gaon reveals a deeper dimension to the necessity of the Yissachar-Zevulun partnership.

On the piece about Rabbah bar bar Chanah’s testimony about “a certain frog” (Bava Basra 73b) the Vilna Gaon teaches (based on ChaZaL) that many a time, a genuine Torah Scholar cannot fulfill his potential and live according to the total dedication to Torah study required of his soul, if he dedicates any time to earning a livelihood. Constraints in the area of making a living are actually assaults of the evil-inclination, the “Yetzer Harah” at hindering the spiritually immeasurably important pursuit of continual Torah study. In truth, the Torah scholar’s “mazal” i.e. “his providentially determined station in life” dictates that he be unsuccessful in making a livelihood, no matter what personal effort he makes; as ChaZaL taught (Moed Katan 28a): “A person’s livelihood is not determined by merit but rather by mazal”. However, this providential decree determining his inability to succeed in a livelihood only applies to efforts that the Torah Scholar himself makes to provide for himself and his family, but does not affect efforts made by others on his behalf, to support him.
Should another Jew come along, whose mazal determines that he will be successful and wealthy, and interject on the Torah Scholars behalf, the Scholar can benefit from the good mazal and fortune of this fellow Jew. Through the partnership of the two each is fulfilling the divine providential plan which was intended for them, to mutually benefit together from each others labors, as opposed to each being lacking and deficient on his own, either in the spiritual realm or the material realm.

This is part of the deeper, practical message behind the episode in the Torah of the bitter waters of Marah, which occurred after leaving Egypt, but before the Jews arrived at Har Sinai (Shemos 15:23). The Torah relates: “They came to Marah, but they could not drink water from Marah because it was bitter; therefore, it was named Marah... The people complained against Moses, saying, What shall we drink? So he cried out to the Lord, and the Lord instructed him concerning a piece of wood (Etz), which he cast into the water, and the water became sweet. There He gave them a statute and an ordinance, and there He tested them”.

The Vilna Gaon explains that “arriving at Marah” a place of “bitter, undrinkable waters” represents when a person comes to this world, like the Torah scholar mentioned above, with a “bad mazal” making a livelihood “bitter, undrinkable” unattainable. The solution is to “cast an Etz (piece of wood)” into the waters to “sweeten them”. Who is the Etz? This is a Zevulun, a supporter of Torah, for the verse in Mishlei (3:18) says:" עֵץ-חַיִּים הִיא לַמַּחֲזִיקִים בָּה"ּ , “It (the Torah) is a tree of life to those who support it”. It does not say that is a tree to those who learn it but rather to those who support it! (Vayikra Rabbah 25:1) Thus supporters of Torah are called “trees of life”, supporters of the lives of those who study Torah day and night. Thus when the “Etz” (wood) intercedes on behalf of the Torah scholar with bitter mazal for livelihood, this sweetens the bitter mazal and allows him to live and continue learning Torah.

Ultimately, the relationship between the Yissachar-Zevulun parallels the relationship between Mashiach ben David and Mashiach ben Yosef is hinted at through many related teachings of ChaZaL. Take this one for example:

אמר ר' יוחנן אם ראית דור שמתמעט והולך חכה לו שנאמר ואת עם עני תושיע 'וגו

“R’ Yochanan said: If you see a generation that is becoming increasingly diminished (impoverished) await/expect him (i.e. Mashiach ben David) as it says: “You save the impoverished nation” (Shmuel II 22:28) – (Sanhedrin 98a)

Part of the deeper message in this ChaZaL relates to what we’ve described above as the ultimate Rectification and Redemption being achieved through the unity of the material and spiritual realms of creation, Zevulun and Yissachar, Mashiach ben Yosef and ben David:

As Kabbalah teaches, the main work and effort of creation is to unite the final letters “Vav” and “Hei” of the Hashem’s Name (י-ה-ו-ה). The Vav corresponds to Yesod and the Hei corresponds to Malchus. When this is achieved, Hashem’s unity can be revealed and this will result in the complete Redemption.

The letter vav is shaped as such that it is wide at the top and then increasingly thinner as it descends and represents the characteristic of Yesod, which channels the spiritual light of the upper sefiros into Malchus, through a process of “tzimtzum” contraction, diminishing and refining the light until it can be appropriately received by the receptive vessel, Malchus. This receiving aspect is embodied in Malchus, the final hei, described as receiving hand of creation (which is why hei in gematria is 5, corresponding to the five fingers of the hand.
Also, the shape of the hei is like the profile of a hand open to receive a coin).
It is also called the “ani” or “poor-person” who receives only that which he is given by Yesod, like a poor-person.

Since it is the primarily physical efforts of Mashiach ben Yosef that lead into the realization of the spiritual efforts of Mashiach ben David, Mashiach ben Yosef & Yesod correspond to the vav characteristics and rectifications of the nation and Mashiach ben David & Malchus correspond to the hei characteristics and rectifications of the nation. This is also why the verse quoted describes the nation as an “impoverished nation” who will be saved/redeemed; and Mashiach ben David himself is described as “a poor man, riding on a donkey” (Zechariah 9:9).

Thus, when you see that a generation has the outstanding quality and characteristics of the rectifications of Mashiach ben Yosef, the vav, Yesod, which “increasingly diminishes” in bestowing upon Malchus, then you have the potential for the manifestation of Mashiach ben David, the hei, the aspect of the “poor person”, the nation manifesting Malchus, “poverty”, the ability to receive the light of Redemption.

And this really what the Yissachar and Zevuluns’ dynamic within the Jewish people is all about. When collectively the two components can unite together, we have the unity of material and spiritual and can begin to convey that message to the rest of the world and eventually return to Gan Eden.

This rectification can also exist within one Jew, when he finds the proper balance in his life between the material and the spiritual aspects of his life and personal world.

(Some additional hints at the Zevulun – Yissachar, Yesod – Malchus, dynamic:
Zevulun was the 6th son born corresponding to Yesod)

Also hinted at in the verse where Zevulun is born and receives his name (Bereishis 30:20)

וַתֹּאמֶר לֵאָה זְבָדַנִי אֱ־לֹהִים אֹתִי זֵבֶד טוֹב הַפַּעַם יִזְבְּלֵנִי אִישִׁי כִּי יָלַדְתִּי לוֹ שִׁשָּׁה בָנִים וַתִּקְרָא אֶת שְׁמוֹ זְבֻלוּן

“And Leah said, "God has given me a good portion. This time, my husband will live with me, for I have borne him six sons"; so she named him Zevulun”

Here Zevulun is Yesod, the 6th sefirah corresponding to the “six sons” leading into Malchus.)

(Also note that Mashiach ben David corresponding to the “Yissachar” with the “bad mazal” who needs the support of Mashiach ben Yosef, the “Zevulun” in the Vilna Gaon’s explanation of Rabbah bar bar Chanah’s teaching, is perhaps hinted at and expressed by ChaZaL who say that David HaMelech, the root of Mashiach ben David, had a bad mazal and destined to die at birth, but Adam took 70 years of his life and added 70 years to then life of David)