The Secret of 5 in the Passover Seder
Why the magic number in Passover is really 5, and not 4

(ב) וַיְדַבֵּ֥ר אֱלֹהִ֖ים אֶל־מֹשֶׁ֑ה וַיֹּ֥אמֶר אֵלָ֖יו אֲנִ֥י יהוה׃ (ג) וָאֵרָ֗א אֶל־אַבְרָהָ֛ם אֶל־יִצְחָ֥ק וְאֶֽל־יַעֲקֹ֖ב בְּאֵ֣ל שַׁדָּ֑י וּשְׁמִ֣י יהוה לֹ֥א נוֹדַ֖עְתִּי לָהֶֽם׃ (ד) וְגַ֨ם הֲקִמֹ֤תִי אֶת־בְּרִיתִי֙ אִתָּ֔ם לָתֵ֥ת לָהֶ֖ם אֶת־אֶ֣רֶץ כְּנָ֑עַן אֵ֛ת אֶ֥רֶץ מְגֻרֵיהֶ֖ם אֲשֶׁר־גָּ֥רוּ בָֽהּ׃ (ה) וְגַ֣ם ׀ אֲנִ֣י שָׁמַ֗עְתִּי אֶֽת־נַאֲקַת֙ בְּנֵ֣י יִשְׂרָאֵ֔ל אֲשֶׁ֥ר מִצְרַ֖יִם מַעֲבִדִ֣ים אֹתָ֑ם וָאֶזְכֹּ֖ר אֶת־בְּרִיתִֽי׃ (ו) לָכֵ֞ן אֱמֹ֥ר לִבְנֵֽי־יִשְׂרָאֵל֮ אֲנִ֣י יהוה וְהוֹצֵאתִ֣י אֶתְכֶ֗ם מִתַּ֙חַת֙ סִבְלֹ֣ת מִצְרַ֔יִם וְהִצַּלְתִּ֥י אֶתְכֶ֖ם מֵעֲבֹדָתָ֑ם וְגָאַלְתִּ֤י אֶתְכֶם֙ בִּזְר֣וֹעַ נְטוּיָ֔ה וּבִשְׁפָטִ֖ים גְּדֹלִֽים׃ (ז) וְלָקַחְתִּ֨י אֶתְכֶ֥ם לִי֙ לְעָ֔ם וְהָיִ֥יתִי לָכֶ֖ם לֵֽאלֹהִ֑ים וִֽידַעְתֶּ֗ם כִּ֣י אֲנִ֤י יהוה אֱלֹ֣הֵיכֶ֔ם הַמּוֹצִ֣יא אֶתְכֶ֔ם מִתַּ֖חַת סִבְל֥וֹת מִצְרָֽיִם׃ (ח) וְהֵבֵאתִ֤י אֶתְכֶם֙ אֶל־הָאָ֔רֶץ אֲשֶׁ֤ר נָשָׂ֙אתִי֙ אֶת־יָדִ֔י לָתֵ֣ת אֹתָ֔הּ לְאַבְרָהָ֥ם לְיִצְחָ֖ק וּֽלְיַעֲקֹ֑ב וְנָתַתִּ֨י אֹתָ֥הּ לָכֶ֛ם מוֹרָשָׁ֖ה אֲנִ֥י יהוה׃

(2) God spoke to Moses and said to him, “I am יהוה. (3) I appeared to Abraham, Isaac, and Jacob as El Shaddai, but I did not make Myself known to them by My name יהוה. (4) I also established My covenant with them, to give them the land of Canaan, the land in which they lived as sojourners. (5) I have now heard the moaning of the Israelites because the Egyptians are holding them in bondage, and I have remembered My covenant. (6) Say, therefore, to the Israelite people: I am יהוה. I will free you from the labors of the Egyptians and deliver you from their bondage. I will redeem you with an outstretched arm and through extraordinary chastisements. (7)And I will take you to be My people, and I will be your God. And you shall know that I, יהוה, am your God who freed you from the labors of the Egyptians. (8)I will bring you into the land which I swore to give to Abraham, Isaac, and Jacob, and I will give it to you for a possession, I יהוה.”

תָּנוּ רַבָּנַן: רְבִיעִי (חמישי) גּוֹמֵר עָלָיו אֶת הַהַלֵּל, וְאוֹמֵר הַלֵּל הַגָּדוֹל, דִּבְרֵי רַבִּי טַרְפוֹן. וְיֵשׁ אוֹמְרִים: ״ה׳ רוֹעִי לֹא אֶחְסָר״.

The Sages taught in a baraita: With regard to the fourth (fifth) cup, one completes hallel over it and recites the great hallel; this is the statement of Rabbi Tarfon.

While some manuscripts note that Rabbi Tarfon references a fourth cup of wine, others note that he is talking about a fifth cup of wine

חמישי אומר עליו הלל הגדול דברי רבי טרפון...

On the fifth cup [of wine] one recites the great Hallel. This is the opinion of Rabbi Tarfon....

(י) וְאַחַר כָּךְ נוֹטֵל יָדָיו וּמְבָרֵךְ בִּרְכַּת הַמָּזוֹן עַל כּוֹס שְׁלִישִׁי וְשׁוֹתֵהוּ. וְאַחַר כָּךְ מוֹזֵג כּוֹס רְבִיעִי וְגוֹמֵר עָלָיו אֶת הַהַלֵּל. וְאוֹמֵר עָלָיו בִּרְכַּת הַשִּׁיר וְהִיא יְהַלְלוּךָ יהוה כָּל מַעֲשֶׂיךָ וְכוּ'. וּמְבָרֵךְ בּוֹרֵא פְּרִי הַגָּפֶן וְאֵינוֹ טוֹעֵם אַחַר כָּךְ כְּלוּם כָּל הַלַּיְלָה חוּץ מִן הַמַּיִם. וְיֵשׁ לוֹ לִמְזֹג כּוֹס חֲמִישִׁי וְלוֹמַר עָלָיו הַלֵּל הַגָּדוֹל מֵ(תהילים קלו-א) "הוֹדוּ לַיהוה כִּי טוֹב" עַד (תהילים קלז-א) "עַל נַהֲרוֹת בָּבֶל". וְכוֹס זֶה אֵינוֹ חוֹבָה כְּמוֹ אַרְבָּעָה כּוֹסוֹת. וְיֵשׁ לוֹ לִגְמֹר אֶת הַהַלֵּל בְּכָל מָקוֹם שֶׁיִּרְצֶה אַף עַל פִּי שֶׁאֵינוֹ מְקוֹם סְעֵוּדָּה:

(10) And afterwards, he recites the Grace after the Meals over a third cup and drinks it. And afterwards, he mixes (pours) a fourth cup and finishes the Hallel (a set order of praises from the Psalms) over it. And he recites the blessing of song and that is "May all of your creatures praise you, etc." And he recites the blessing, "Who creates the fruit of the vine," and does not taste anything afterwards the whole night, except for water. And he should mix (pour) a fifth cup and say upon it the Great Hallel (Psalms 136), from "Give thanks to the Lord, for God is good" (Psalms 136:1) to "Upon the waters of Babylon" (Psalms 137:1). And this cup is not obligatory like the [other] four cups. And he can finish the Hallel anyplace that he desires, even though he is not in the place of the meal.

Vilna Gaon, 18th Century

We have the custom of pouring a fifth cup and calling it the Cup of Elijah the prophet. The reason is that there is a dispute in the Gemara over whether one needs a fifth cup, and the halakhah is not determined. When Elijah comes, the doubt will be clarified. Therefore, based on this doubt, the cup is poured but not drunk, and it is called the Cup of Elijah, for when he comes, all doubts will be clarified, including this doubt.

(ד) מזגו לו כוס שני, וכאן הבן שואל אביו. ואם אין דעת בבן, אביו מלמדו: מה נשתנה הלילה הזה מכל הלילות, שבכל הלילות אנו אוכלין חמץ ומצה, הלילה הזה כלו מצה. שבכל הלילות אנו אוכלין שאר ירקות, הלילה הזה מרור. שבכל הלילות אנו אוכלין בשר צלי שלוק ומבשל, הלילה הזה כלו צלי. שבכל הלילות אנו מטבילין פעם אחת, הלילה הזה שתי פעמים. ולפי דעתו של בן אביו מלמדו. מתחיל בגנות ומסים בשבח, ודורש מארמי אובד אבי (דברים כו, ה), עד שיגמור כל הפרשה כלה.

(4) They pour a second cup [of wine] for him. And here the son questions his father. And if the son has insufficient understanding [to question], his father teaches him [to ask]: Why is this night different from all [other] nights? On all [other] nights, we eat leavened and unleavened bread, [but] on this night, [we eat] only unleavened bread. On all [other] nights, we eat all kinds of vegetables, [but] on this night, [we eat only] bitter herbs. On all [other] nights, we eat meat roasted, stewed or boiled, [but] on this night, [we eat] only roasted [meat]. On all [other] nights, we dip [vegetables] once, [but] on this night, we dip [vegetables] twice. And according to the son's intelligence, his father instructs him. He begins [answering the questions] with [the account of Israel’s] shame and concludes with [Israel’s] glory, and expounds from “My father was a wandering Aramean” until he completes the whole passage.

There are really 5 questions, or 1 header, and 4 sub questions. Why do we call them "Four Questions" when there are really five? Perhaps it’s so that someone will ask about it, thus leading to more questions. The four questions originally functioned as a guide for the child at the table who didn’t know how to ask questions, thus enabling him to fulfill his obligation to ask questions even though he didn’t have any of his own. Eventually, these four questions morphed into a prescribed part of the Passover liturgy. Nonetheless, questioning at the Passover table isn’t limited to the 4/5 questions; the rituals are meant to provoke questions. The rabbis in the Talmud say that during a Passover Seder, someone should pick up and remove the table from the room. This bizarre ritual, the rabbis note, is meant to elicit the children who are no longer at the table to ask: "What’s going on here?" or "Why is this night different than all other nights (Pesachim 115b)?" Why do we have two hand washings in the Haggadah (Urchatz and Rochtzah), the first of which has no blessing, yet the second one does? For the very same reason it seems; to confound participants into inquiry. In other words, we should build in strangeness into the narrative in order to provoke questions. ––Josh Franklin

Who knows four? I know four: four are the mothers, three are the fathers, two are the tablets of the covenant, One is our God in the heavens and the earth. Who knows five? I know five: five are the books of the Torah, four are the mothers, three are the fathers, two are the tablets of the covenant, One is our God in the heavens and the earth.

מַעֲשֶׂה בְּרַבִּי אֱלִיעֶזֶר וְרַבִּי יְהוֹשֻׁעַ וְרַבִּי אֶלְעָזָר בֶּן־עֲזַרְיָה וְרַבִּי עֲקִיבָא וְרַבִּי טַרְפוֹן שֶׁהָיוּ מְסֻבִּין בִּבְנֵי־בְרַק וְהָיוּ מְסַפְּרִים בִּיצִיאַת מִצְרַיִם כָּל־אוֹתוֹ הַלַּיְלָה, עַד שֶׁבָּאוּ תַלְמִידֵיהֶם וְאָמְרוּ לָהֶם רַבּוֹתֵינוּ הִגִּיעַ זְמַן קְרִיאַת שְׁמַע שֶׁל שַׁחֲרִית.

It happened once [on Pesach] that Rabbi Eliezer, Rabbi Yehoshua, Rabbi Elazar ben Azariah, Rabbi Akiva and Rabbi Tarfon were reclining in Bnei Brak and were telling the story of the exodus from Egypt that whole night, until their students came and said to them, "The time of [reciting] the morning Shema has arrived."

By the Grace of G-d
11th of Nissan, 5717
Brooklyn, N.Y
Greeting and Blessing:
The Festival of Pesach is inaugurated by the central theme: “When thy son will ask thee,” and the Haggadah is based on the commandment of the Torah: “Then shalt thou tell thy son.”There are various ways of asking questions and formulating the answers, depending upon whether the son belongs to the category of the “Wise,” the “Wicked,” the “Simple,” or “The One Who Knows Not How to Ask.”While the “Four Sons” differ from one another in their reaction to the Seder service, they have one thing in common: they are all present at the Seder service.
Even the so-called “Wicked” son is there, taking an active, though rebellious, interest in what is going on in Jewish life around him. … This justifies the hope that someday also the “Wicked” one will become wise.Unfortunately … there is another kind of a Jewish child: the child who is conspicuous by his absence from the Seder service; the one who has no interest whatsoever in Torah and Mitzvoth … who is not even aware of the Seder-Shel-Pesach or the Exodus from Egypt.This presents a grave challenge … For no Jewish child should be forgotten or given up.
We must make every effort to save also that “lost” child and bring the absentee to the Seder table. … With determination and a deep sense of responsibility, we need have no fear of failure.In order to remedy such a situation it is necessary to attack the roots of the problem.The regrettable truth is that the blame for the above-mentioned “lost generation” lies largely with the parents. … Some immigrants arriving in a new and strange environment believed that the way to overcome difficulties was to assimilate quickly by discarding the heritage of their forefathers and abandoning the Jewish way of life. …They persuaded themselves and their children that in their new surroundings the observance of Torah and Mitzvoth did not fit.
… By this attitude they hoped to assure their children’s existence and survival in the new environment. But what kind of existence is it if everything spiritual and holy is traded for the material?… Thousands upon thousands of Jews became removed from their fountain of life and from their true faith. Children grew up who no longer belong even to the “Four Sons” of the Haggadah.The event of the Exodus from Egypt and the Festival of Passover remind us that not imitation of the environment ensures survival, but loyalty to our traditions and way of life.
Our ancestors in Egypt were also a small minority and lived in difficult circumstances. Yet they preserved their identity and clung with pride to their traditions. Precisely in this way their existence was assured and their redemption came.It is therefore one of the vital tasks of our time to awaken in the young generation … a deeper appreciation of the true values of Torah-true Yiddishkeit … and the realization that only true Yiddishkeit can guarantee the existence of each and every Jew, at any time and in any place.
There is no room for hopelessness in Jewish life, and no Jew should ever be given up as a lost cause. Through the compassionate approach of Ahavas Yisroel, even those of the “lost” generation can be brought back to the love of G-d and the Torah … and eventually be elevated to the rank of the “Wise” son.May G-d grant that all sons and daughters of Israel be gathered together at the same Seder table, celebrating Passover in its true spirit … and may this hasten the complete Redemption through Moshiach, speedily in our time.
With the blessing of a Kosher and Happy Pesach.
Rabbi Menachem Mendel Schnearson

ת"ר כוס חמישי אומרים עליו הלל הגדול דברי רבי טרפון. וי"א יהוה רועי לא אחסר. ורשב"ם גורס רביעי אומרים עליו הלל הגדול דכוס חמישי מאן דכר שמיה. ואם בא לומר כוס חמישי רשות ואם ירצה יעשה כוס חמישי הכי הוה ליה למימר הרוצה לעשות כוס חמישי אומר עליו הלל הגדול. אבל לפי גירסת הספרים משמע דלר' טרפון וי"א כוס חמישי הוה ליה חובה ונהגו העולם לעשות רשות. וכן כתב ה"ר יוסף טוב עלם ז"ל שאם הוא תאב לשתות יעשה כוס חמישי. משמע מתוך דבריו שאסור לשתות אחר ארבע כוסות. ותימה דמנלן הא דלקמן לא קאמר אלא דאין מפטירין אחר הפסח אפיקומן היינו שלא לאכול אבל למשתי שרי. וכן נמי מדפריש בירושלמי דבין שלישי לרביעי לא ישתה משום דשמא ישתכר. מכלל דאי לאו חיישינן לשכרות היה מותר לשתות. ומנהג פשוט הוא שלא לשתות יין ופי' הר"ם ז"ל טעם למנהג לפי שחייב אדם לעסוק כל הלילה בהלכות פסח וביציאת מצרים לספר בנסים ובנפלאות שעשה לנו הקב"ה ולאבותינו עד שתחטפנו שינה ואם ישתה ישתכר. והכי אמרינן בתוספתא פ"י חייב אדם לעסוק בהלכות פסח וביציאת מצרים כל הלילה. וזה ששנינו מעשה בר' אליעזר ור' יהושע שהיו מסובין בבני ברק והיו מספרים ביציאת מצרים כל הלילה וכו'. אבל בכוס רביעי התירו שיש לו סמך מן הפסוק כנגד ולקחתי אתכם. מהיכן הלל הגדול. אמר רב יהודה מהודו עד על נהרות בבל רבי יוחנן אמר משיר המעלות עד על נהרות בבל רב אחא בר יעקב אומר מכי יעקב בחר לו יה עד על נהרות בבל אבל מנהגא דעלמא כרב יהודה בהלל הגדול.

Our rabbis learned, "We say the Great Hallel (Psalm 136, and see below at the bottom of the paragraph for other opinions) over a fifth cup - these are the words of Rabbi Tarfon, and there are those that say, 'The Lord is my shepherd, I shall not lack' (Psalms 23)." And Rashbam [follows] the textual variant, "We say the Great Hallel on the fourth cup," as 'who mentioned the name' of the fifth cup; and if it is coming to say [that the fifth cup is optional and, if wants, he should do a fifth cup, this is how it should have said it: "One who wants to do a fifth cup should say the Great Hallel upon it." But according to the textual variant of the books, it is implied that for Rabbi Tarfon and the 'those that say,' the fifth cup is obligatory, but the world has become accustomed to make it optional. And so did Rabbi Yosef Tov Eelem, may his memory be blessed, write - that if desires to drink, he should make a fifth cup. It is implied from his words that it is [otherwise] forbidden to drink after the four cups. And it is a wonder, as from where do we have this; as later it only says, "We may not eat an afikoman (a dessert or other foods eaten after the meal) after [we are finished eating] the Pesach sacrifice" - which means not to eat, but to drink is permitted. And so also since in the [Talmud] Yerushalmi, it explains that he should not drink between the third and fourth [cups] because of 'lest he get drunk,' it is implied that if we were not concerned about drunkenness, it would be permissible to drink. But the custom that has spread is not to drink wine. And Ram, may his memory be blessed, explained a reason for this custom: that it is because a person is obligated to be involved the whole night with the laws of Pesach and with the exodus from Egypt, to recount the miracles and wonders that the Holy One, blessed be He, did for us, until slumber overcomes him - and if he drinks, he will get drunk [and not be able to do this]. And so too do we say in Tosefta Pesachim 10:11, "A person is obligated to be involved with the laws of Pesach and with the exodus from Egypt the whole night"; and this is what we learned (Pesach Haggadah, Magid, Story of the Five Rabbis 1), "It happened once [on Pesach] that Rabbi Eliezer, Rabbi Yehoshua [...] were reclining in Bnei Brak and were telling the story of the exodus from Egypt that whole night, etc." But with the fourth cup, they permitted [drinking], as it has scriptural support, corresponding to the verse (Exodus 6:7), "and I will take you." From where is the Great Hallel? Rav Yehuda said from "Praised" (Psalms 136:1) to "On the rivers of Babylon" (Psalms 137:1). Rabbi Yochanan said from "A song of ascents" to "On the rivers of Babylon." Rab Achaa bar Yaakov says from "Since the Lord has chosen Yaakov" (Psalms 135:4) to "On the rivers of Babylon." But the custom of the world is like Rav Yehuda concerning the Great Hallel.

(י) וְאַחַר כָּךְ נוֹטֵל יָדָיו וּמְבָרֵךְ בִּרְכַּת הַמָּזוֹן עַל כּוֹס שְׁלִישִׁי וְשׁוֹתֵהוּ. וְאַחַר כָּךְ מוֹזֵג כּוֹס רְבִיעִי וְגוֹמֵר עָלָיו אֶת הַהַלֵּל. וְאוֹמֵר עָלָיו בִּרְכַּת הַשִּׁיר וְהִיא יְהַלְלוּךָ יהוה כָּל מַעֲשֶׂיךָ וְכוּ'. וּמְבָרֵךְ בּוֹרֵא פְּרִי הַגָּפֶן וְאֵינוֹ טוֹעֵם אַחַר כָּךְ כְּלוּם כָּל הַלַּיְלָה חוּץ מִן הַמַּיִם. וְיֵשׁ לוֹ לִמְזֹג כּוֹס חֲמִישִׁי וְלוֹמַר עָלָיו הַלֵּל הַגָּדוֹל מֵ(תהילים קלו א) "הוֹדוּ לַיהוה כִּי טוֹב" עַד (תהילים קלז א) "עַל נַהֲרוֹת בָּבֶל". וְכוֹס זֶה אֵינוֹ חוֹבָה כְּמוֹ אַרְבָּעָה כּוֹסוֹת. וְיֵשׁ לוֹ לִגְמֹר אֶת הַהַלֵּל בְּכָל מָקוֹם שֶׁיִּרְצֶה אַף עַל פִּי שֶׁאֵינוֹ מְקוֹם סְעֵוּדָּה:

(10) And afterwards, he [washes] his hands and recites the Grace over the Meal over a third cup and drinks it. And afterwards, he pours a fourth cup and finishes the Hallel over it. And he recites the blessing over the song, and that is "May all of your creatures praise you, etc." And he recites the blessing, "who creates the fruit of the vine," [drinks it] and does not taste anything afterwards the whole night except for water. And he should pour a fifth cup and say the Great Hallel (Psalms 136) upon it, from "Give thanks to the Lord, for He is good" (Psalms 136:1) to "Upon the rivers of Babylon" (Psalms 137:1). And this cup is not obligatory like the [other] four cups. And he can finish the Hallel in any place that he desires, even though he is not in the place of the meal.