The Mishna tells us that even an impoverished Jew on the night of the Seder should eat in a reclining manner, as do free and independent people, on a couch as a demonstration of freedom. In addition, the poorest of the poor, one who only receives one meal a day from communal funds, must strive with all his might to acquire wine, including selling his garments, for four cups during the Seder, if the community does not provide it for him. This is all done to express the concept freedom. Pesachim 99b.
It is interesting that the same effort is not required for the acquisition of Matzah even though eating Matzah is a Torah requirement while the requirement of the four cups of wine is purely Rabbinic. Indeed, the Torah makes no mention whatsoever of the four cups of wine.
The source of this requirement is brought down in the Midrash. “Rav Huna in the name of Rav Benaya said, ‘This (the four cups) is an allusion to the four terms of redemption that are stated prior to the Exodus from Egypt. (God says, I will remove, I will save, I will redeem, and I will take. Shemot, 6, 6-7. )’” Bereisheet Rabba, 88:5.
The concept of the four cups and their usage is controversial in the Talmud.
Rav Yehuda said in the name of Shmuel, “These four cups of wine . . .if he drank them at one time, one immediately after the other, he has fulfilled the Mitzvah. Rava said, he has only fulfilled the requirement of drinking four cups of wine, but he has not fulfilled the requirement of expressing Cherut, or freedom. Rav said, “he has not fulfilled even the Mitzvah of four cups of wine.” Pesachim, 108b.
The Rashbam explains that according to Rav, he has fulfilled the Mitzvah of being festive on the holiday and that the four cups are considered as only one cup, and thus he must drink three additional cups according to the prescribed order. See Rashbam, ad locum.
The prescribed order is as follows:
The First cup is for Kiddush or the sanctification of the day. It does not however, have the framework of the regular Kiddush. Normally, Kiddush could be said before nightfall to increase sanctity from the profane to the holy (Tosefet Yom Tov). On Pesach, it must be said after nightfall. If this is to be one of the four cups which express freedom, it has to be directly related to the Matzah and the Maror which can only be eaten after nightfall.
The Second cup is utilized for the recognition of redemption. Rabbi Akiva maintains that this blessing is not simply one over a Mitzvah, but it contains a petition to God for redemption and acceptance, and thus, this blessing must have also a concluding blessing. See Pesachim 116b.
The Third cup is called the Cup of Blessing for it concludes the Grace after the Meal. Pesachim 117b.
The Fourth cup of wine is connected to the Hallel, and the blessing is known as the Blessing of the Song, and is an expression of the praise of God. Pesachim 117b.
With regard to the Third Cup, the Gemara states:
Rav Chanan said to Rava, “we learn from this (the Mishnaic requirement that one needs to drink wine after the Grace after Meal at the Seder) that the Grace after Meals requires the blessing over a cup of wine. Rava said to him that all the four cups of wine were established by Rabbis as an expression of freedom, but every one of them must be connected to the fulfillment of a separate Mitzvah. Pesachim 117b.
The Rashbam explains this concept in the following manner:
This issue is discussed in the Mishnah (Berachot 54b). However, the Mishnah does not openly state that Grace requires a cup of wine. We have to make the deduction that wine is required after the Grace. Rashbam, Pesachim, 117b (citing to Pesachim 105b).
The Rashbam asks, why do we need to learn this law as a result of a deduction, when it is openly stated in the Mishnah at Pesachim 117b? The Rashbam explains that the four cups of wine that the Rabbis ordained to express freedom, must be connected to the performance of a Mitzvah. The rest of the year this is not necessary, and even here, the main purpose of the cup of wine is not the Grace but rather the concept of freedom. Rashbam Pesachim 117b.
Why are the four cups of wine required to be connected to a Mitzvah? The answer reveals to us what the nature of freedom truly is which is demonstrated by these cups. A Jew can only express and experience freedom through the performance of Mitzvot and obedience to the will of God.
Kiddush is the ability to sanctify the world in which we live, both in terms of space and time. Redemption is crucial to our relationship with God and it occurs through a Bakasha, a petition, as an act of prayer. The Third blessing is an act of thankfulness or Hodaah. It is a statement of thanksgiving for all the gifts that God has bestowed upon us. The final cup recognizes the sovereignty and uniqueness of God and the praise we offer him through the Hallel. These cups establish the basis of Jewish thought and are thus crucial for the understanding of the Haggadah, for they specifically explain what freedom truly is. This is why we call Pesach the time of our freedom.
This idea is also expressed in Pirkei Avot. It says in Shemot, “And the tablets are the creation of God and the writing is the writing of God which is engraved (Charut) upon the tablets.” Exodus 32:16. “Rav Yehoshua ben Levi said, . . .do not read this Charut, but rather Cherut (freedom), for there is no freedom for man except for one who engages with the Torah.” Avot 6:2.
It seems paradoxical that there is no freedom for a Jew unless he engages with the Torah through learning it and observing its commandments. However, that is the proposition established by the four cups. We can now understand why the four cups have become so essential for Jewish life. They establish the meaning of the festival of Pesach and the foundation of Judaism.
This Dvar Torah is in honor of the Yahrtzeit of my father, Moshe ben Yosef.