The Four Cups: Their Purpose and Number
1א
מתני׳ ערב פסחים סמוך למנחה לא יאכל אדם עד שתחשך אפילו עני שבישראל לא יאכל עד שיסב ולא יפחתו לו מארבע כוסות של יין ואפילו מן התמחוי:
MISHNA: On the eve of Passover, adjacent to minḥa time, a person may not eat until dark, so that he will be able to eat matza that night with a hearty appetite. Even the poorest of Jews should not eat the meal on Passover night until he reclines on his left side, as free and wealthy people recline when they eat. And the distributors of charity should not give a poor person less than four cups of wine for the Festival meal of Passover night. And this halakha applies even if the poor person is one of the poorest members of society and receives his food from the charity plate.
2ב

Wikipedia: "Symposium"

In ancient Greece, the symposium (Greek: συμπόσιον symposion or symposio, from συμπίνειν sympinein, "to drink together") was a part of a banquet that took place after the meal, when drinking for pleasure was accompanied by music, dancing, recitals, or conversation.

The Greek symposium was a key Hellenic social institution. It was a forum for men of respected families to debate, plot, boast, or simply to revel with others. They were frequently held to celebrate the introduction of young men into aristocratic society. Symposia were also held by aristocrats to celebrate other special occasions, such as victories in athletic and poetic contests. They were a source of pride for them.

Symposia were usually held in the andrōn (ἀνδρών), the men's quarters of the household. The participants, or "symposiasts", would recline on pillowed couches arrayed against the three walls of the room away from the door.

The men at the symposium would discuss a multitude of topics—often philosophical, such as love and the differences between genders.

A symposium would be overseen by a "symposiarch" who would decide how strong the wine for the evening would be, depending on whether serious discussions or merely sensual indulgence were in the offing. The Greeks and Romans customarily served their wine mixed with water, as the drinking of pure wine was considered a habit of uncivilized peoples.

3 ג
4 ד
5ה

Questions: In what ways do the four cups make the Seder similar to a symposium? In what ways are they different?

6ו
ולא יפחתו לו מארבעה: היכי מתקני רבנן מידי דאתי בה לידי סכנה והתניא לא יאכל אדם תרי ולא ישתה תרי ולא יקנח תרי ולא יעשה צרכיו תרי אמר רב נחמן אמר קרא (שמות יב, מב) ליל שמורים ליל המשומר ובא מן המזיקין רבא אמר כוס של ברכה מצטרף לטובה ואינו מצטרף לרעה רבינא אמר ארבעה כסי תקינו רבנן דרך חירות כל חד וחד
We learned in the mishna that even with regard to the poorest of Jews, the charity distributors should not give him less than four cups of wine. The Gemara asks: How could the Sages establish a matter through which one will come to expose himself to danger? But wasn’t it taught in a baraita: A person should not eat pairs, i.e., an even number of food items; and he should not drink pairs of cups; and he should not wipe himself with pairs; and he should not attend to his sexual needs in pairs. The concern was that one who uses pairs exposes himself to sorcery or demons. Why would the Sages require one to drink an even number of cups and thereby place himself in a position of danger? Rav Naḥman said that the verse said: “It was a night of watching to the Lord” (Exodus 12:42), which indicates that Passover night is a night that remains guarded from demons and harmful spirits of all kinds. Therefore, there is no cause for concern about this form of danger on this particular night. Rava said a different answer: The cup of blessing for Grace after Meals on Passover night is used in the performance of an additional mitzva and is not simply an expression of freedom. Therefore, it combines with the other cups for the good, i.e., to fulfill the mitzva to drink four cups, and it does not combine for the bad. With regard to the danger of drinking pairs of cups, it is as though one drinks only three cups. Ravina said: The Sages instituted four separate cups, each of which is consumed in a manner that demonstrates freedom. Therefore, each and every one
7ז
מצוה באפי נפשה הוא
is a distinct mitzva in its own right. In other words, each cup is treated separately and one is not considered to be drinking in pairs.
8ח
א"ר יהודה אמר שמואל ארבעה כוסות הללו צריך שיהא בהן כדי מזיגת כוס יפה שתאן חי יצא שתאן בבת אחת יצא השקה מהן לבניו ולבני ביתו יצא שתאן חי יצא אמר רבא ידי יין יצא ידי חירות לא יצא שתאן בבת אחת רב אמר ידי יין יצא ידי ארבעה כוסות לא יצא השקה מהן לבניו ולבני ביתו יצא אמר רב נחמן בר יצחק והוא דאשתי רובא דכסא
Rav Yehuda said that Shmuel said: These four cups must contain enough undiluted wine to allow for diluting a significant cup. In talmudic times, people would not drink pure wine. They would dilute it with water, generally adding three times as much water as wine. If one drank them undiluted, he has fulfilled his obligation. If one drank them all at once, i.e., he poured all four cups of wine into one large cup and drank it, he has fulfilled the obligation. If one gave his sons or the members of his household to drink from them, he has nevertheless fulfilled the obligation. The Gemara now addresses each of these rulings of Shmuel in turn. Shmuel said that if one drank them undiluted he has fulfilled his obligation. Rava said: He has fulfilled the obligation to drink the four cups of wine, but he has not fulfilled the obligation to drink in a way that expresses freedom, which is the preferable way to fulfill the mitzva, as aristocrats do not drink undiluted wine. If one drank the four cups all at once, Rav said that he has fulfilled the obligation to drink wine as an expression of rejoicing on the Festival, but he has not fulfilled the obligation to drink four cups, which requires four distinct cups, each drunk separately. Shmuel also stated that if one gave his sons or the members of his household to drink from them, he has nevertheless fulfilled his obligation. Rav Naḥman bar Yitzḥak said: And this is the case only if he himself drank the majority of the cup.
9ט
מתני׳ מזגו לו כוס שלישי מברך על מזונו רביעי גומר עליו את הלל ואומר עליו ברכת השיר בין הכוסות הללו אם רוצה לשתות ישתה בין שלישי לרביעי לא ישתה: גמ׳ א"ל רב חנן לרבא ש"מ ברכת המזון טעונה כוס א"ל ארבע כסי תיקנו רבנן דרך חירות כל חד וחד נעביד ביה מצוה: רביעי גומר עליו את ההלל ואומר עליו ברכת השיר:
MISHNA: They poured for the leader of the seder the third cup of wine, and he recites the blessing over his food, Grace After Meals. Next, they pour him the fourth cup. He completes hallel over it, as he already recited the first part of hallel before the meal. And he also recites the blessing of the song at the end of hallel over the fourth cup. During the period between these cups, i.e., the first three cups established by the Sages, if one wishes to drink more he may drink; however, between the third cup and the fourth cup one should not drink. GEMARA: Ran Ḥanan said to Rava: Since the mishna states that Grace After Meals must be recited over the third cup, learn from it that Grace After Meals requires a cup of wine. Rava said to him: This is no proof, for although the Sages instituted the drinking of four cups in the manner of freedom, once the four cups are in place, with each and every one of them we will perform a mitzva, despite the fact that they were not originally instituted for this purpose. After the Sages instituted these four cups, they attached a special mitzva to each one. However, this does not prove that there is an obligation to recite Grace After Meals over a cup of wine during the rest of the year. We learned in the mishna that they pour the leader of the seder the fourth cup and he completes hallel over it, and he recites the blessing of the song at the end of hallel over that cup.
10י
ואפילו עני שבישראל לא יאכל עד שיסב: איתמר מצה צריך הסיבה מרור אין צריך הסיבה יין איתמר משמיה דרב נחמן צריך הסיבה ואיתמר משמיה דרב נחמן אין צריך הסיבה ולא פליגי הא בתרתי כסי קמאי הא בתרתי כסי בתראי אמרי לה להאי גיסא ואמרי לה להאי גיסא אמרי לה להאי גיסא תרי כסי קמאי בעו הסיבה דהשתא הוא דקא מתחלא לה חירות תרי כסי בתראי לא בעו הסיבה מאי דהוה הוה ואמרי לה להאי גיסא אדרבה תרי כסי בתראי בעו הסיבה ההיא שעתא דקא הויא חירות תרי כסי קמאי לא בעו הסיבה דאכתי עבדים היינו קאמר השתא דאיתמר הכי ואיתמר הכי אידי ואידי בעו הסיבה

We learned in the mishna that even the poorest of Jews should not eat until he reclines. It was stated that amora’im discussed the requirement to recline. Everyone agrees that matza requires reclining, i.e., one must recline when eating matza, and bitter herbs do not require reclining. With regard to wine, it was stated in the name of Rav Naḥman that wine requires reclining, and it was also stated in the name of Rav Naḥman that wine does not require reclining. The Gemara explains: And these two statements do not disagree with each other: This statement is referring to the first two cups, and that statement is referring to the last two cups. However, it was not clear which two cups require reclining according to Rav Naḥman. Some say the explanation in this manner and some say it in that manner. The Gemara elaborates: Some say it in this manner, that the first two cups require reclining, as it is now that freedom begins. Since reclining is a sign of freedom, while discussing the exodus from Egypt it is appropriate to drink while reclining. By contrast, the last two cups do not require reclining, because what was already was. In other words, by this point one has completed the discussion of the Exodus and has reached the latter stages of the seder. And some say it in that manner and claim that on the contrary, the last two cups require reclining, as it is at that time that there is freedom. However, the first two cups do not require reclining, as one still says: We were slaves. The Gemara concludes: Now that it was stated so, and it was stated so, i.e., there are two conflicting opinions and it cannot be proven which two cups require reclining, both these sets of cups and those require reclining.

11יא
מניין לארבעה כוסות רבי יוחנן בשם ר' ר' בנייה כנגד ארבע גאולות (שמות ו) לכן אמור לבני ישראל אני ה' והוצאתי אתכם וגו' ולקחתי אתכם לי לעם וגומר והוצאתי והצלתי וגאלתי ולקחתי רבי יהושע בן לוי אמר כנגד ארבעה כוסות של פרעה (בראשית מ) וכוס פרעה בידי ואשחט אותם אל כוס פרעה ואתן את הכוס על כף פרעה ונתת כוס פרעה בידו וגו'. רבי לוי אמר כנגד ארבעה מלכיות ורבנן אמרי כנגד ד' כוסות של פורענות שהקב"ה עתיד להשקות את אומות העולם (ירמיהו כה, טו) כי כה אמר ה' אלהי ישראל אלי קח את כוס היין החימה וגו' כוס זהב בבל ביד ה' (תהילים עה) כי כוס ביד ה' (תהילים יא) ימטר על רשעים פחים אש וגפרית ורוח זלעפות מנת כוסם מהו מנת כוסם רבי אבין אמר

What is the source for the four cups? R. Yochanan, in the name of R. Benayah [said], they are parallel to the four terms of redemption: “Thus, say to the people of Israel, I am God, and [1] I will bring them out…[2] and I will save them…[3]and I will redeem them…[4]and I will take them to be My people…”(Exodus 6:6-7).

Rabbi Joshua ben Levi says, they are parallel to the four cups of Pharaoh: [1]“And the cup of Pharaoh was in my hand…[2] and I squeezed [the grapes] into the cup of Pharaoh [3] and I gave the cup of Pharaoh to the hand of Pharaoh…”(Genesis 40:11). [4] “And you will place the cup of Pharaoh in his hand…” (Genesis 40:13).

Rabbi Levi said, they are parallel to the four kingdoms [prophesied by Daniel; interpreted by the sages as being Babylon, Media/Persia, Greece, and Rome].

The sages say, they are parallel to the four cups of punishment that God will rain on the nations of the world in the future: [1] “take the wrathful cup of wine” (Jeremiah 25:15); [2] “the golden cup of Babylon is in the hand of God” (Jeremiah 51:7); [3] “for the cup is in God’s hand” (Psalms 75:9); [4] “a scorching wind shall be their cup” (Psalms 11:6; trans. JPS). What is “their cup”? Rabbi Avun says,

12יב

דיפלי פוטירין כדיפלי פוטירין אחר המרחץ וכנגד עתיד הקב"ה להשקות את ישראל ארבעה כוסות של נחמות (תהילים טז) ה' מנת חלקי וכוסי (תהילים כג) דשנת בשמן ראשי כוסי רויה והדין (תהילים קטז) כוס ישועות אשא תריין.

the drippings of poterion [a shrub that can be turned into a medicinal potion]; like a vial of poterion after a bath.

Parallel to [these cups]: in the future, the holy One, blessed be He, will cause Israel to drink four cups of comfort: [1] “God is my portion and cup” (Psalms 16:5); [2] “you anoint my head with oil, my cup overflows” (Psalms 23:5); and the verse [3-4] “I will raise the cup of salvations” (Psalms 116:13) counts as two.