At Kadesh – we drink the first of the four cups of wine. Each of the four cups of wine symbolizes the four highlights of the seder at which we drink one of the cups: the first at Kadesh, the second at Maggid, the third at Barech and the fourth at Hallel.
The ability of a kiddush is to draw a distinction between that evening and other evenings. The way we do this is through remembering Yetzias Mitzrayim – the Exodus. We do this through a passing mention of “זכר ליציאת מצרים“- in memory of Yetzias Mitzrayim. The reason we do this is because Yetzias Mitzrayim is the שרש – the root – of being Hashem’s people. The Sefer Hachinuch goes so far as to say that most mitzvos do have a direct link to Yetzias Mitzrayim.
The function of any kiddush is to express service, allegiance and fealty to Hashem. This is true of kiddush on every Shabbos and all Yomim Tovim. This is the first cup of wine that we drink.
The second is drunk at Maggid. Maggid’s place in the Seder is to perform the mitzva of סיפור יציאת מצרים – the in depth discussion of the events of Yetzias Mitzrayim - rather than the זכר of Kadesh. The function of the mitzva of סיפור יציאת מצרים is to recreate and relive the events, rather than to remember. The wording of the halacha is “כל דור ודור חייב אדם לראות את עצמו כאלו הוא יצא עתה” -
To fulfill the mitzva of סיפור , there are three requirements. The first is the most basic – the engagement that occurs in question and answer form. This engagement constitutes a dialogue that differentiates it from the monologue of a זכר . This is the educational aspect of סיפור .
The second requirement of סיפור is for the Seder to envision Yetzias Mitzrayim. This is achieved through the story telling aspect of Maggid. As with any story, it begins with a problem and ends with a solution.
The final, most demanding requirement of סיפור is the טעמי הצמוות – the rationale behind the mitzvos of the Seder must be explained and understood.
R’ Chaim Brisker says that these requirements distinguish the mitzva of סיפור from the regular mitzva of זכר . The mitzva of סיפור constitutes a key highlight of the Seder, and this is why the second cup of wine is drunk at the end of Maggid.
The third cup is consumed at the conclusion of Birchas Hamazon, Barech. The function of the bracha is to give thanks to Hashem for what we have eaten – so the bracha goes back on all the אכילות מצוה – the Matza, Marror as well as the meal. The instructions to perform these mitzvos created the circumstances through which we could leave Egypt – the Jews had to eat the Korban Pesach the night the Egyptian firstborns died. The bracha of Birchas Hamazon is the conclusion of all the mitzvos of the evening, and as such, is as much key highlight as the mitzvos themselves were, and the reason we drink the third cup of wine at this point.
The fourth cup is drunk at the conclusion of Hallel. Hallel is a shira, a song of praise and gratitude for all the kindness Hashem has done for us, which is what the whole Seder was about.
Wine is chashuv – it is prestigious and indicates prominence. It is with wine that we mark the prominent events of the Seder, and as we have now seen, the junctures at which we drink encompass the entire evening.