Why do we drink four cups of wine at the Seder?
The most famous answer to this question revolves around two verses in Sh’mos/Exodus (6:6-7):
“Therefore, say to the children of Israel ‘I am Hashem, and I SHALL TAKE YOU OUT from under the burdens of Egypt; I SHALL RESCUE YOU from their service; I SHALL REDEEM YOU with an outstretched arm and with great judgments. I SHALL TAKE YOU TO ME for a people and I shall be a G-d to you….”
In these two verses, we find what are termed “The Four Expressions of Redemption.” G-d said to the nation of Israel using four different expressions that they would be taken out of slavery in Egypt. We therefore drink a cup of wine, on this night that we commemorate our redemption, for each expression of redemption that G-d uttered.
The Sh”lah gives another reason. On this night, we celebrate the birth of the Jewish people as a nation. We read in the Hagadah about our forefathers. Avraham originally worshipped idols. His son Yitzchak had two children, Yaakov and Esav. Yaakov ended up in Egypt where his son Yosef was. However, we do not read of the contributions of our mothers to the development of the nation of Israel. Each cup of wine represents one of our matriarchs. The first cup of wine is used to recite Kiddush, the sanctification of the day. In the Kiddush, we read how G-d has sanctified the nation of Israel with His mitzvos (commandments), which makes the Jewish people unique. Sarah was known for her efforts to spread the word of G-d to those who previously worshipped idols. It is with Kiddush, where we speak of this sanctification of the nation of Israel, that we commemorate Sarah, who exerted efforts to bring others into this fold.
We drink the second cup of wine after we have told the story of the birth of our nation. We have read how Avraham originally worshipped idols. We have read how the nation grew and developed. Rivka’s life progressed in a similar fashion. She was born into a family of idol worshipers and she grew to be one of the matriarchs of the nation of Israel. With the second cup of wine, we commemorate Rivka, who overcame an idolatrous background to become the mother of the Jewish people.
After we conclude the Grace After Meals, we drink the third cup. Rachel was the mother of Yosef, who assured that the entire land of Egypt would have sustenance during the years of famine. It is fitting that we remember Rachel, the mother of the one who sustained a nation, after we have completed our meal.
The last cup of wine is drunk after we complete Hallel, the praises of G-d. Leah, upon the birth of her son Yehudah, said “This time I shall thank Hashem.” Why did Leah thank G-d upon the birth of her fourth son, and not with the previous three? The answer is that Leah realized that Yaakov was to have 12 children between his four wives. When she had her fourth son, she realized that she was given one more than her “share” in the unit that was the base for the nation of Israel. Of course she was thankful with each child. But with Yehudah, Leah knew that she had received something truly special, above and beyond what she should get. Therefore, she thanked Hashem when Yehudah was born. It is fitting that after we finish thanking Hashem for taking us out of Egypt, we remember Leah, who taught the Jewish people how and when to say thank you.