The Four Cups of the Seder are structurally connected to the four verbal performances this evening:
(1) Kiddush, sanctifying the holiday
(2) Maggid, the storytelling
(3) Birkat HaMazon, completing the Pesach meal; and
(4) Hallel, completing the festival Psalms.
The Talmud connects the Four Cups to God's Four Promises to Israel: "Tell the children of Israel: I am Adonai! I will take them out... I will rescue them… I will redeem them… and I will marry them taking them as my people and I will be their God" (Exodus 6:6-7, Jerusalem Talmud Pesachim 10:1).
However, two 16th C. mystic rabbis identify the Four Cups with the Four Matriarchs of Israel. The Maharal of Prague (famous for the legend of Golem) and Rav Isaiah Horowitz of Tsfat explain:
(1) The Cup of Kiddush stands for Sarah who was the mother of a community of converts, believers by choice.
(2) The Cup of Maggid is for Rebecca who knew how to mother both Esav and Jacob, two opposed natures.
(3) The Cup of the Blessing after Eating represents Rachel whose son Joseph provided the whole family of Jacob with bread in a time of great famine.
(4) The Cup of Hallel (Praise) is for Leah who came to realize that the pursuit of the impossible, Jacob's love, must give way to appreciation of what one has. When her fourth child was born, Judah, she praised God: "This time I will thank God" (Genesis 29:35).
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