Four Cups

Exegetical Approaches

Overview

In explaining the purpose of the Four Cups at the Seder and their relationship to the four liturgical sections with which they are associated, commentators differ over which is paramount.  The Ba'alei HaTosafot consider the Cups to be merely a secondary accompaniment to the four sections of the Haggadah in which Hashem's praises are sung.  For them, reciting the liturgy over a cup filled with wine is a way of adding importance to the liturgy.  R. David Bonafed and the Maharal, in contrast, view the act of drinking itself as an expression of freedom and a way of reenacting our ancestors' redemption.  According to them, the drinking is the central fulfillment, while it is the accompanying liturgy which is only secondary.  A third approach, adopted by Rambam, contends that there exists a dual obligation which consists of both components.

Cups of Blessing to Accompany the Liturgy

The four cups of wine serve as an accompaniment to the four sections of the Haggadah (Kaddesh, Maggid, Birkat HaMazon, and Hallel) which sing Hashem's praises.  They do not, however, constitute their own independent obligation.

Sources:Perhaps RashbamPesachim 108bAbout R. Shemuel b. Meir, TosafotPesachim 99bSukkah 38aAbout Ba'alei HaTosafot¹

Relationship to recitations of Kiddush, Maggid, Bareikh, and Hallel – Bavli BerakhotBerakhot 35aAbout the Bavli brings down in the name of R. Yonatan that one should sing Hashem's praises over wine ("אין אומרים שירה אלא על היין").  Thus, Kiddush and Birkat HaMazon are regularly recited over wine, while the unique Seder sections of Maggid and Hallel which glorify Hashem's redemption of the Children of Israel are similarly sung over a cup of wine.²

Why four? According to this approach, there is no special significance to the number four.  It so happens that there are four parts of the Seder liturgy in which we "toast" Hashem's miracles, and thus there are four cups of wine.³

"שתאן בבת אחת" – Can one drink all four at once? Since the liturgy is what is important, drinking all four cups at once defeats the purpose and does not fulfill the obligation of the Four Cups.  This corresponds to the literal reading of Bavli PesachimPesachim 108a-109aAbout the Bavli which says: "ידי ארבעה כוסות לא יצא".  Regarding the Bavli's additional statement that one who does so nonetheless fulfills the obligation of "wine" ("ידי יין יצא")‎,⁴ Rashbam and Tosafot both contend that this refers only to the separate mitzvah of rejoicing on Yom Tov.⁵

Who needs to drink? Ba'alei HaTosafot⁶ suggest that the head of the household can discharge the obligation of the Four Cups for all those present,⁷ exactly as happens with Kiddush on Shabbat ("דמאי שנא ארבע כוסות מקידוש דכל השנה שאחד מוציא את כולם").‎⁸  This is possible only because, according to them, the primary obligation of the Four Cups is the recital of words of praise upon them, while the actual drinking is merely secondary.⁹  It is this position of theirs which enables them to draw a parallel to Kiddush on Shabbat.¹⁰

One obligation or four? This approach views each cup as its own individual obligation, disconnected from the other three.¹¹

Necessary shiur (רוב כוס)? R. Nachman b. Yitzchak states in Bavli PesachimPesachim 108a-109aAbout the Bavli that one must drink "the majority of a cup" ("והוא דאשתי רובא דכסא") to fulfill one's obligation on Pesach.  At first glance, this appears to be different than by Kiddush for which one must drink only a "cheekful" or "כמלא לוגמיו".  Ba'alei HaTosafot,¹² though, in line with their understanding that the Four Cups are no different than Kiddush, explain that "רובא דכסא" really means only "כמלא לוגמיו".‎¹³

Status of undiluted wine ("שתאן חי") – Rava in Bavli PesachimPesachim 108a-109aAbout the Bavli states regarding undiluted wine:  "ידי יין יצא, ידי חירות לא יצא".  Rashbam and Tosafot interpret this to mean that although diluting the wine to improve its taste is not absolutely critical for the fulfillment of the basic obligation of reciting praise over wine,¹⁴ it is the preferable method of discharging the obligation.¹⁵

Women's obligation – According to Tosafot, the Bavli PesachimPesachim 108a-109aAbout the Bavli which obligates women in the Four Cups ("because they too were part of the miracle" – "שאף הן היו באותו הנס") is referring to their obligation to participate in the four sections of the Seder which are recited over the wine, rather than to the actual act of drinking wine.¹⁶  Tosafot notes that even though women are generally exempt from saying Hallel, the Hallel on the night of Pesach is unique, as it is recited because of the miracle of the Exodus.¹⁷

Are children obligated? Bavli PesachimPesachim 108a-109aAbout the Bavli records a dispute between Tanna Kamma and R. Yehuda as to whether young children ("תינוקות") are obligated in the Four Cups.  From the Gemara, it is difficult to determine the age of the child under discussion, but Rashbam appears to understand that the disagreement is in the case of a toddler who is not old enough to understand what the mitzvah is about ("לא הגיע לגיל חינוך"),‎¹⁸ and Tanna Kamma extends the obligation even to him.¹⁹  According to Rashbam, even R. Yehuda would agree that a minor old enough to understand the performance of the liturgical sections of the Seder ("קטן שהגיע לחינוך") would be obligated to recite these sections over four cups of wine.²⁰

Reclining while drinking – Even though, the four cups are not intrinsically related to freedom, Tosafot would likely maintain that the requirement of reclining while drinking them stems from the fact that the passages which are recited upon them do relate to redemption.²¹

Fifth cup – Some manuscripts of Bavli Pesachim²² cite R. Tarfon as stating that the fifth cup is for the recital of Hallel HaGadol.

Demonstration of Freedom

Drinking four cups of wine proclaims our status as free people and is a fulfillment of "חַיָּב אָדָם לְהַרְאוֹת אֶת עַצְמוֹ כְּאִלוּ הוּא יָצָא מִמִּצְרַיִם" and, perhaps, publicizing the miracle.

Sources:Perhaps RashiPesachim 108aPesachim 108bAbout R. Shelomo Yitzchaki, R. David BonafedPesachim 107aPesachim 108b "שתאן חי"Pesachim 108b "שתאן בבת אחת"Pesachim 108b "אמר ר' יהודה"Pesachim 109b, MaharalGevurot Hashem 48About R. Judah Loew of Prague

Relationship to recitations of Kiddush, Maggid, Bareikh, and Hallel – According to R. David and the Maharal, the basic primary obligation to drink four cups of wine is not dependent on reciting any particular liturgical passages.²³  Only a secondary or more complete fulfillment of the mitzvah²⁴ links the cups to particular sections of the Seder.²⁵

Women's obligation – This approach could explain that the very drinking of the four cups of wine publicizes the miracle of the redemption (פרסומי ניסא).‎²⁶  As such, women are obligated since they too were part of the miracle ("שאף הן היו באותו הנס").‎²⁷

Are children obligated? According to R. David, the dispute between Tanna Kamma and R. Yehuda in Bavli PesachimPesachim 108a-109aAbout the Bavli is even regarding children who have reached the standard age of education ("הגיעו לגיל חינוך") for regular mitzvot.  While Tanna Kamma maintains that the mitzvah of Four Cups is the same as all other mitzvot,²⁸ R. Yehuda rules that the regular obligation of חינוך does not apply to it.²⁹  R. David explains that the Four Cups are unique because their objective is to display freedom, and since even an older child is not capable of imbibing wine like an adult,³⁰ there is also no obligation of training him to perform this mitzvah.³¹

Why four? According to this approach, wine must be drunken in abundance as an expression of freedom or happiness.  The Yerushalmi PesachimPesachim 10:1About the Yerushalmi records various opinions as to why the number four was chosen:³²

• Four expressions of redemption – R. Yochanan connects the four cups to the four verbs (ארבע לשונות גאולה) in Shemot 6 which speak of Hashem's salvation.
• Four cups of Paroh – R. Yehoshua b. Levi relates them to the four references to Paroh's cup in the butler's dream in Bereshit 40.³³
• Four kingdoms – According to R. Levi, they symbolize the four kingdoms that have oppressed the Children of Israel.³⁴
• Four cups of wrath and consolation – The Rabbis in the Yerushalmi suggest that the four cups correspond to the four cups of calamity that are to be given to the enemies of Israel in the future and the four cups of consolation that Hashem will give Israel to drink.³⁵

"שתאן בבת אחת" – Can one drink all four at once? According to this position, even if one drank all four cups consecutively, rather than in their proper places in the Haggadah, one still fulfills one's obligation, and R. David cites the YerushalmiPesachim 10:1About the Yerushalmi as proof for this.  This approach must therefore reinterpret the BavliPesachim 108a-109aAbout the Bavli's statement:  "שתאן בבת אחת – ידי יין יצא, ידי ארבעה כוסות לא יצא", since at face value this appears to imply that in such a case one does not fulfill the obligation of the Four Cups.  This can be accomplished in two different ways:

• Rashi limits the application of the Bavli's ruling to a case in which one drank four cups worth of wine from a single cup.³⁶  According to this interpretation, even the Bavli would agree that the obligation is fulfilled if one drinks the wine from four separate cups, and the problem is only that drinking from a single cup cannot be considered to be four separate cups no matter how much one drank.
• Alternatively, R. David suggests that even the Bavli concurs that the basic obligation was realized, and it only means that the action was not performed in the preferred way.

One obligation or four? R. DavidPesachim 109b asserts that it is only the cumulative effect of all four cups together which fulfills the obligation.  According to him drinking a single cup or two does not accomplish anything, as this is not an extraordinary action and therefore does not demonstrate freedom.  To maintain this position, he needs to reinterpret Ravina's statement in Bavli Pesachim 109bPesachim 109b-110aAbout the Bavli.³⁷

Who needs to drink? Each individual at the Seder must drink their own four cups of wine, as eating or drinking is not an action which can be performed by one person on behalf of another.³⁸

Necessary shiur (רוב כוס)? R. DavidPesachim 107a maintains that each of the Four Cups require drinking the majority of the cup ("רוב כוס", like the simple reading of Bavli PesachimPesachim 108a-109aAbout the Bavli), rather than just a "cheekful".  His reasoning is that the mitzvah is to drink four cups, and less than most of the cup would not be considered drinking a cup.³⁹

Status of undiluted wine ("שתאן חי") – R. David explains the statement of Rava in Bavli PesachimPesachim 108a-109aAbout the Bavli:  "ידי יין יצא, ידי חירות לא יצא" to mean that one fulfills one's basic obligation but not in an optimal way.  Since the Four Cups are intended to express freedom, it is preferable that the wine be diluted and drunken properly.

Reclining while drinking – It is logical that the cups are drunk while reclining since both actions are meant to symbolize freedom.

Fifth cup – A version of the Yerushalmi is citedRaavad cited by Orchot Chayyim Hilkhot Leil HaPesach 13About R. Avraham b. David as saying that R. Tarfon states that the fifth cup corresponds to the fifth term of redemption "וְהֵבֵאתִי".  R. David suggests that even R. Tarfon agrees that there are only four obligatory cups, and the fifth is just optional.

Combination

The obligation to drink four cups of wine is a dual one, relating to both their being an accompaniment to liturgical praise and their being an expression of freedom.

Sources:RambamChametz uMatzah 7:6-10Megillah VeChanukah 4:12About R. Moshe b. Maimon as explained by RY"Z SoloveitchikGriz Hilchot Chametz uMatzah 7:9

"שתאן בבת אחת" – Can one drink all four at once? Rambam rules that this would discharge only the obligation of drinking an abundance of wine to demonstrate freedom,⁴⁰ but not the requirement of reciting various sections of the Haggadah over wine.⁴¹

Reclining while drinking – Rambam integrates the laws of reclining and the Four Cups, as both manifest our status as free people.

Why four? As there are four points in the Seder where one sings Hashem's praises, they are each accompanied by a cup of wine.

Who needs to drink? As the obligation is not only to praise but also to drink as an expression of freedom, everyone must drink.

Are children obligated? Rambam does not mention that there is an obligation to provide Four Cups for minors, even those of educable age.  His silence on this point may be an indication that he maintains that there is, in fact, no obligation.⁴²

Necessary shiur (רוב כוס)? Rambam requires a "רוב כוס", rather than just a "cheekful", since part of the mitzvah is to drink in abundance.

Status of undiluted wine ("שתאן חי") – According to the Rambam, with improperly prepared wine, one can discharge the obligation of reciting over wine, but one cannot fulfill the obligation of expressing freedom.⁴³

¹ This is the simple understanding of Tosafot Pesachim 99bPesachim 99bAbout Ba'alei HaTosafot's position (that the head of the household can fulfill the obligation of Four Cups for everyone) and the analogy they draw to Kiddush on Shabbat.  It is also how R. Y"Z SoloveitchikHilchot Chametz uMatzah 7:9 explains their opinion, and it is even more explicit in Tosafot Sukkah 38aSukkah 38aAbout Ba'alei HaTosafot.
R. Zvi Pesach Frank (Mikraei Kodesh, Pesach, Vol. II, p. 101) offers an alternative interpretation which suggests that Baalei HaTosafot do not dispute that the focus is on the drinking itself (like R. David below), but merely maintain that Four Cups is a mitzvah incumbent on the household, similar to lighting Chanukkah candles.  However, while this understanding could perhaps be viable for Tosafot Pesachim (though, according to it, one would have expected Tosafot to draw a parallel to Chanukkah candles instead of to Kiddush), it does not work with the more explicit formulation of Tosafot Sukkah.

² See also the formulation of the Ran Pesachim 99b:  "ולא יפחתו לו מארבע כוסות של יין – תקנו אותם חכמים לארבע ברכות כדי שתהא כל אחת על כוס".  See below, however, that Bavli Pesachim 117bPesachim 117bAbout the Bavli appears to imply the opposite.

³ See, however, Rashbam and Tosafot Pesachim 99b who cite the correlation of Bereshit Rabbah and Yerushalmi between the Four Cups and the four expressions of redemption.  For elaboration regarding the Yerushalmi, see below.

⁴ The Rif and some manuscripts of the Bavli read:  "ידי חירות יצא".  See also the Rambam below.

⁵ See Bavli Pesachim 109a that rejoicing on Yom Tov is achieved through drinking wine ("במה משמחם ביין").  This interpretation of "ידי יין יצא" encounters some difficulty, as the fact that one fulfills one's obligation of rejoicing on Yom Tov would seem to be so plainly obvious that it would not even require stating.  See the Baalei HaTosafot who consequently struggle to explain the הוה אמינא that one might not discharge this obligation.  It may be simpler, however, to explain that the words "ידי יין יצא" (even though obvious) appear merely as a contrast to the obligation ("ידי ארבעה כוסות" or "ידי חירות") which one does not fulfill.

⁶ This is also the position taken by the Rivevan Pesachim 108a (Mirsky ed. p. 62):  "‏מצוה לטעום כולן מד' כוסות, אבל אם שתה אחד מן המסובין רובא דכסא יצאו כולן ידי חובתן.  הכי מוכיח בעירובין פרק בכל מערבין (מ':).‏"

⁷ See the Maharal below who challenges the Tosafist parallel to Kiddush, and claims that the Four Cups should be compared to Matzah and Maror which each individual must eat for themselves.  In practice, Baalei HaTosafot, themselves, also recommend that one be strict and provide four cups of wine for each person present.

⁸ Tosafot notes that this is the implication of the Bavli PesachimPesachim 108a-109aAbout the Bavli which says "השקה מהן לבניו ולבני ביתו יצא", implying that each person did not have their own cup.  Cf. the Ittur who explains that the Bavli is referring only to minors who do not yet have their own obligation, and the Mordechai who says that it speaks of a case where the minors had already drunken their own cups.  Compare also to the interpretations of R. David and the Maharam Chalava below.

⁹ See the Maharal below who challenges the Tosafist parallel to Kiddush, and claims that the Four Cups should be compared to Matzah and Maror which each individual must eat for themselves.

¹⁰ On Shabbat, in fact, if one has no wine one is even able to fulfill the mitzvah over bread.  The wine itself is thus obviously not essential.

¹¹ This would seem to be supported by the simple reading of Ravina's words in Bavli Pesachim 109b-110aPesachim 109b-110aAbout the Bavli:  "כל חד וחד מצוה באפי נפשה הוא".  Cf. R. David's interpretation below.

¹² See Tosafot Pesachim 107a s.v. "אם" and 108b s.v. "רובא".

¹³ To be considered a "cup" it must measure at least a "רביעית", or a fourth of a "לוג".  Since a majority of a "רביעית" is identical to the measurement of a "cheekful", it is possible that this is the meaning of the gemara.

¹⁴ See Tosafot Pesachim 108b s.v. "שתאן חי" who here too equates the requirements of the Four Cups with a regular "כוס של ברכה".

¹⁵ There seems to be some inconsistency between the way Rashbam and Tosafot interpret "ידי יין יצא" here and the way they interpret the same words in the case of "שתאן בבת אחת".

¹⁶ According to Tosafot, women have no obligation to actually drink the wine, and it is only required that the individual leading the Seder actually drink (see above).  This would work in tandem with the opinion of R. Yehuda in Bavli Pesachim 109a that women (in contrast to men) are not required to drink wine to fulfill the mitzvah of rejoicing on Yom Tov.

¹⁷ Thus, according to Tosafot, "שאף הן היו באותו הנס" is really explaining why women are obligated in Maggid and Hallel and, only by extension, in the cups of wine upon which they are recited.  Women are also obligated in Kaddesh and Bareikh, and hence in their cups of wine as well, but not for the reason of "שאף הן".

¹⁸ Rashbam may distinguish between the terms "קטן" (used to describe a child who is already at the education stage), and "תינוק" (a younger child who is not yet at the age of חינוך).  The term "תינוק", however, is used in Tannaitic sources to refer to both a קטן שלא הגיע לחינוך (see Mishna Shabbat 19:4) and a קטן שהגיע לחינוך (see Mishna Niddah 6:11).

¹⁹ See also the MaharilSefer Maharil Seder HaHaggadah 9 who rules in accordance with this position.  According to this approach, Tanna Kamma maintains that, in addition to the standard obligation that older children perform mitzvot for education (חינוך) reasons, on the night of the Seder there is an additional requirement that even younger children (שאינם יודעים לשאול) participate, as they too were redeemed and were part of the miracle (and thus, their parents are obligated to ensure their participation). [However, see R. David below who rejects this possibility.]  R. Yehuda, though, rejects this notion, arguing that there is no point in toddlers going through the motions if they have not yet reached an age when the actions have any meaning for them.

²⁰ Since the main purpose of the cups is to accompany the liturgical sections, there is no reason that the rules for them should be different than for any other mitzvah (see also Shulchan Arukh HaRavOrach Chayyim 472:25).  TosafotPesachim 99bAbout Ba'alei HaTosafot, on the other hand, maintain that R. Yehuda exempts even an older child at the age of חינוך.  According to them, R. Yehuda's logic might be that since even an older child is not capable of drinking wine properly, there is also no reason for him to recite the liturgy over wine (cf. the explanation of RambamChametz uMatzah 7:6-10About Rambam Hilchot's position presented by the Peri ChadashOrach Chayyim 472:15).
The RoshResponsa 14:5 and Shulchan ArukhOrach Chayyim 472:15 rule that one needs to provide Four Cups for a child of educable age ("הגיע לחינוך").  They thus chart a middle ground between the positions of the Rambam and Maharil.   However, it is unclear how they understand the dispute between Tanna Kamma or R. Yehuda, and according to whom they are ruling.

²¹ This is easier to understand by the cases of Maggid and Hallel.

²² See also Halakhot Gedolot and Rambam Chametz UMatzah 8:10.

²³ See also Rashi Pesachim 108a s.v. "ארבע כוסות" who states that three of the cups correspond to the three mentions of "כּוֹס" in Bereshit 40:11, while the fourth is for Birkat HaMazon.  Cf. the Yerushalmi Pesachim cited below, and note that Rashbam Pesachim 108a does not incorporate Rashi's interpretation.

²⁴ See R. David's formulation:  "שאין עכוב בדבר אלא שלא קיים מצוה כהלכתה".  R. David's view, that the Gemara is speaking of a single main obligation albeit with an added dimension of a preferred method of performance, differs fundamentally from the Rambam (below) who understands that there are two completely distinct obligations (like the simple interpretation of Bavli Pesachim 108b).

²⁵ This appears to be the simple reading of Bavli Pesachim 117bPesachim 117bAbout the Bavli.  See also the MeiriPesachim 117bAbout R. Menachem HaMeiri who, in interpreting the Bavli, explains that the obligation of the Four Cups preceded that of the Seder liturgy.  According to him, the liturgy was established to accompany the drinking of the cups, rather than the other way around.

²⁶ Cf. Maggid MishnehHilchot Megillah VeChanukah 4:12.

²⁷ This would work nicely with the position cited in the name of R. Moshe Soloveitchik that "שאף הן היו באותו הנס" applies only to mitzvot whose essence is to publicize the miracle.

²⁸ It is possible that the dispute between Tanna Kamma and R. Yehuda might be regarding whether the Four Cups are primarily intended to accompany the Haggadah's liturgical sections or to display freedom through the drinking itself.  If so, Rashbam and Tosafot above would be championing Tanna Kamma's opinion, while R. David would be adopting R. Yehuda's position.

²⁹ R. David cites the Mishna Sukkah 3:15 and Bavli Sukkah 42a as proof that the age of education (גיל חינוך) varies depending on the mitzvah and is not the same across the board.  Thus, according to R. Yehuda, a child could be of educable age for other mitzvot, but not for the obligation of Four Cups.  This is also the position of the Tashbetz in Maamar Chametz 117.  In fact, he permits the drinking of the Four Cups only for someone who has reached the (legal drinking) age of 21:

אבל קטנים אין מחנכין בזה כשאר מצות. (וכדאמרינן) [וכדאמר רבי יהודה] מה תעלה לתינוקות ביין. דכיון שאין נהנין בו אינו להם דרך חירות. וגם הרופאים אומרים כי היין לקטנים הוא [כ]תוספת אש על אש בעצים תלושים. ולא התירוהו עד שיעברו על הקטן שלש שבועות שנים.

³⁰ Grape juice first became available only in the twentieth century, and some but not all agree that it can be used to fulfill the obligation of the Four Cups.  Even according to those that it cannot, it is possible that it could be used to fulfill the obligation of חינוך (this depends on the dispute over whether a fulfillment for the sake of education must be identical in all of its respects to the regular fulfillment of an adult).  However, grape juice was not yet an option or consideration in medieval times.

³¹ R. David is thus consistent with his general approach that the obligation of the Four Cups comes primarily to demonstrate freedom.  It appears (though it is not explicit) that R. David rules in accordance with the opinion of R. Yehuda, and his opinion is adopted by the Ran.  Cf. Rambam below.

³² None of the opinions cited in the Yerushalmi suggest that there needed to be four cups because of the four sections of the Haggadah in which one drinks the cups, and it would appear that according to the Yerushalmi this was only a later development.

³³ See also Rashi Pesachim 108a cited above.  It is difficult to find a fundamental connection between the four cups of wine and the four "cups" of Paroh.  See, Rabbi Jacob J. Schacter, "Seeking Redemption in an Unredeemed World: Yosef at the Seder", And You Shall Transmit to Your Children... A Pesach Haggadah (New York, 2014): 25-30, who suggests that the Yosef narratives are recalled on Leil HaSeder because they teach important lessons about the nature of the process of redemption.

³⁴ R. Levy might suggest that it is appropriate to recall all our enemies on Pesach, in keeping with the idea that Pesach is a prototype for all future oppressions, and thus all salvations.  This is expressed in the words of the Haggadah: "וְהִיא שֶׁעָמְדָה לַאֲבוֹתֵינוּ וְלָנוּ שֶׁלֹּא אֶחָד בִּלְבָד עָמַד עָלֵינוּ לְכַלּוֹתֵנוּ, אֶלָּא שֶׁבְּכָל דּוֹר וָדוֹר עוֹמְדִים עָלֵינוּ לְכַלּוֹתֵנוּ, וְהַקָּדוֹשׁ בָּרוּךְ הוּא מַצִּילֵנוּ מִיָּדָם."

³⁵ This position might be the opposite of R. Levi's.  While R. Levi focuses on the oppression, the Rabbis focus on our future salvation from them, a major theme of Pesach.

³⁶ This interpretation is adopted also by Raavan Pesachim 108b.

³⁷ Although Ravina asserted "כל חד וחד מצוה באפיה נפשיה", R. David explains that he does not mean to say that the Four Cups constitute four separate mitzvot, but rather only that each is attached to a separate mitzvah.  According to R. David, Ravina is merely a slightly different formulation of Bavli Pesachim 117bPesachim 117bAbout the Bavli "והואיל ואיכא כל חד וחד נעביד ביה מצוה".

³⁸ Although the Bavli PesachimPesachim 108a-109aAbout the Bavli which says "השקה מהן לבניו ולבני ביתו יצא" would seem to imply that not everyone had their own cup, R. DavidPesachim 108b "שתאן בבת אחת" explains that this ruling is speaking only of a huge cup (e.g. Stanley Cup) in which each successive person drank the majority of what remained in the cup (and there was at least a רביעית remaining for the last person).  This is consistent with R. David's opinion below that each person must drink a רוב כוס.  [A similar approach is taken by the Maharam Chalava, except that according to him the cup needs to be big enough only for each person to drink a רביעית, as he maintains that one does not need to drink a רוב כוס even on Pesach.]

³⁹ Kiddush during the rest of the year, however, only requires a cheekful, as the focus there is not on the drinking itself.  Thus, a more minimal amount suffices.

⁴⁰ Rambam's version of the Bavli read: "ידי חירות יצא", like the Rif and some extant manuscripts (see note above).

⁴¹ As opposed to Rashi and R. David above who contend that the words of the Bavli "ידי ארבעה כוסות לא יצא" negate only the optimal fulfillment of the mitzvah, Rambam maintains that there is a second separate obligation which was not discharged at all.  Rambam's interpretation would appear to be supported by the literal reading of the Bavli's formulation.

⁴² This is how the Peri ChadashOrach Chayyim 472:15 understands Rambam's position.  The Peri Chadash contrasts Rambam's silence regarding the Four Cups with his explicit ruling that educable children must eat Matzah.  Cf. the discussion of R. David above and the explanation of the position discussed there.

⁴³ As opposed to all of the commentators above who contend that the Bavli negates only the fulfillment of the mitzvah at its optimal level, Rambam maintains that "לא יצא" means that there is a second separate obligation which was not discharged at all.