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בָּרוּךְ אַתָּה ה' אֱלהֵינוּ מֶלֶךְ הָעולָם אֲשֶׁר קִדְּשָׁנוּ בְּמִצְותָיו וְצִוָּנוּ לַעֲסוק בְּדִבְרֵי תורָה:

Blessing for Torah Study

Barukh Atah Adonai Eloheinu Melekh Ha'Olam Asher Kideshanu Bemitzvotav Vetzivanu La'asok Bedivrei Torah

Blessed are you Adonai, our God, Sovereign of Eternity, who has made us holy through Your mitzvot (sacred calls) and called upon us to immerse ourselves in the words of Torah.

The Four Cups of Wine at the Passover Seder

(ו) לָכֵ֞ן אֱמֹ֥ר לִבְנֵֽי־יִשְׂרָאֵל֮ אֲנִ֣י יְהֹוָה֒ 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 יְהֹוָה֙ 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 יְהֹוָֽה׃

(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.”

אַרְבַּע כָּסֵי תִּיקְּנוּ רַבָּנַן דֶּרֶךְ חֵירוּת, כֹּל חַד וְחַד נַעֲבֵיד בֵּיהּ מִצְוָה.

The Sages instituted the drinking of four cups wine as an expression of freedom, and through each and every one of them we will perform a mitzva.

Rabbi Daniel Landes
There are two obligations in relation to wine on Passover. One is to experience cherut, freedom. Wine gives pleasure and induces a feeling of liberation (though it is to be "pleasant" and grape juice should be available for those who have difficulty with wine). The second is that each of the four cups of wine is an organizing anchor for a different part of the Seder. The first cup is the Kiddush, which declares the sanctity of the day, an obligation on every sacred day. Over the second cup we recite Maggid, the telling of the Passover story, the central purpose of the Haggadah. A third cup is added to the Birkat Hamazon, not just at the seder but on all august occasions. The fourth cup is connected to Hallel (praise) which concludes the Seder.

מְנַיִין לְאַרְבָּעָה כוֹסוֹת. רִבִּי יוֹחָנָן בְּשֵׁם רִבִּי בְנָייָה. כְּנֶגֶד אַרְבַּע גְּאוּלוֹת. לָכֵ֞ן אֱמֹ֥ר לִבְנֵֽי־יִשְׂרָאֵל֘ אֲנִ֣י יְי וְהֽוֹצֵאתִ֣י אֶתְכֶ֗ם וגו׳. וְלָֽקַחְתִּ֨י אֶתְכֶ֥ם לִי֙ לְעָ֔ם וגו׳. וְהֽוֹצֵאתִ֣י. וְהִצַּלְתִּ֥י. וְגָֽאַלְתִּ֤י. וְלָֽקַחְתִּ֨י.

From where the Four Cups? Rebbi Joḥanan in the name of Rebbi Benaiah: Corresponding to the four redemptions [found in Exodus 6:6-7): Therefore, say to the Israelite people, I am יהוה and I will free you, etc. And I will take you as My people, etc. I will free you, I will deliver you, I will redeem you, I will take you.

יען כי כשנעיין יפה נמצא ד' ענינים שונים בד' מאמרים אלו, אשר כל פרט ופרט הוא ענין שלם כשהוא לעצמו ושוה הודאה מיוחדת, כי במאמר הראשון [והוצאתי] מבואר שיוציאם הקב"ה מתחת סבלות מצרים, כלומר שיקל עליהם עבודתם, אבל אין במשמע שיחופשו בכולם מעבודתם, ועל זה הוסיף ואמר והצלתי אתכם מעבודתם, והיינו שלא יעבדו כלל, ואמנם גם לאחר אלה ההנחות עדיין הם עבדי פרעה ואין גאולתם שלמה, הוסיף ואמר וגאלתי אתכם, ויחד עם כל אלה עדיין אינם לעם מיוחד וקנין הקב"ה, ע"ז הוסיף לומר ולקחתי אתכם לי לעם והייתי לכם לאלקים. ומבואר דבמאמרים אלו כלולים ענינים מיוחדים בכלל הגאולה,

וכיון שכן, מבואר פשוט, שעל כל פרט ופרט שבו מעלה יתירה מחויבים בהודאה, ולכן תקנו ד' כוסות של הודאה, ודו"ק. –

ומה שלא תקנו כוס הודאה לענין והבאתי אתכם אל הארץ, דאין לומר מפני שאינו מענין הגאולה, שהרי כמו כן תקנו לענין ולקחתי אתכם לי לעם שהוא ג"כ אינו מענין הגאולה – י"ל פשוט מפני שבהיותנו עתה בגלות והארץ מסורה בידי זרים אי אפשר לישא כוס יין על זה. ואולי לזכר זה תקנו כוס מיוחד לשמו של אליהו לזכרון ורמז שאנו מקוים לביאתו ולתחיית האומה והארץ ב"ב. .
(ירושלמי פסחים פ"י ה"א)

Rabbi Baruch Epstein (1860–1941)

When we examine it well we find that there are four different ideas expressed in these four terms, and each one is its own complete idea unto itself and deserving of its own thanksgiving. In the first statement ("I will take you out"), we see that the Holy Blessed One took them out from under the labors of the Egyptians, which is to say that God lightened their labors--but they were not freed completely. Then God added to this, "And I will save you from their servitude," which means that they did not serve them at all. But even after these two promises, they were still servants to Pharaoh and had not achieved full redemption. Thus God added, "And I will redeem you," but even so they were not yet made a special acquisition of the Holy Blessed One, and so God added "And I will take you to me to be a people, and I will be a god to you." We see that within these sayings are included separate notions of redemption.

As such, the simple meaning is revealed: We are obligated to give thanks for each individual act that increased the redemption. And that is why [the Sages] established the four cups of thanksgiving.

And why did they not establish a cup for the phrase "and I will bring you to the land?" We cannot say that it is because that language is not related to the redemption, since they established a cup for "and I will take you to me to be a people," which is likewise not specifically an aspect of redemption. Rather, the simple answer is that since we are still in exile, and the land is in the hands of non-Jews, it is impossible to raise a glass of wine for this. And perhaps, in recognition of this, they established a special cup in the name of Elijah, as a remembrance and hint that we hope for his coming and for the resurrection of the nation and the land speedily in our days.

(ו) לָכֵ֞ן אֱמֹ֥ר לִבְנֵֽי־יִשְׂרָאֵל֮ אֲנִ֣י יְהֹוָה֒ 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 יְהֹוָה֙ 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 יְהֹוָֽה׃

(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.”

Questions for Discussion
How might we understand the four different types of "redemptions" or "freedoms"? First physically free then psychologically free? What else? What other types of freedoms, and what would it mean to celebrate them with each cup at the seder? What relationship might we make to these freedoms through the rest of the year?
And what about the fifth cup? How does that come into play? What does it represent?