The message of the four cups on Passover
In the four questions we list four differences that are prominent on the night of the Seder as opposed to other nights: eating only matzah and no leavened bread, eating marror (bitter herbs), dipping two times, and eating and drinking while reclining. A difference that’s neglected is the obligation to drink four cups of wine, which doesn’t exist on other nights. Why is this difference not mentioned in the Haggadah?
What is the origin of the four cups of wine? It’s actually a dispute. The most famous reason is that there are four expressions of redemption mentioned in the Torah with connection to the Exodus: והוצאתי, I (G-d) will take you out, והצלתי, I will save you, וגאלתי, I will redeem you, ולקחתי, and I will take you [to Me to be a nation]. Corresponding to these four expressions, Chazal instituted the four cups of wine. A less known reason is connected to the story of when Yosef was framed and put in prison. There he met the שר האופים, minister of the bakers and the שר המשקים, minister of the cup-bearers (a sort of butler). The latter two were thrown in prison and were awaiting their sentence. One night they both had a disturbing dream and asked Yosef to interpret it. When the Torah describes the dream of the שר המשקים and its interpretation, the word כוס, cup, is mentioned four times. The four cups of wine that we drink at the Seder correspond to these four instances. While the numbers match up, what does the dream of the שר המשקים have to do with Pesach?
The prophet Yirmiyahu describes what happened when the Jews were exiled from Israel by the nation of Babylon. He describes a vision of the matriarch Rachel crying for her children. Her cries echoed in the heavens and were accepted by Hashem. Why is it specifically Rachel? Undoubtedly the other foremothers were crying, yet only Rachel’s cries are mentioned in the verse.
The Jewish nation’s cries against the attacks from the Babylonians, the Edomites and the Amalekites stems from their overt baseless hatred they have for the Jews. Most nations when they conquer a different nation don’t destroy all of their buildings. Rather, once captured, they add the buildings to their nation. This is not true with these nations. When the Edomites captured Jerusalem, they didn’t stop there; they destroyed the temple and all the surrounding buildings. All of this came from pure hatred.
When Reuven goes before a King and pleads for help from what Shimon did to him, perforce Reuven can’t have done the same injustice himself. Otherwise, why should the King bother to help Reuven when he himself is guilty of the same crime? The same is true with the other foremothers, who were surely crying when their descendants were sent into exile. Their cries couldn’t have been answered, because their children were just as guilty of baseless hatred. The ten sons of Yaakov sold Yosef to the Egyptians due to their baseless hatred. Only Rachel and her children were clean from this sin. Yosef was the victim and Binyomin was too young to be involved in the sale. Therefore, only her cry regarding the baseless hatred being done to the Jews was answered.
The ruling of Pharaoh to reinstate the שר המשקים and to execute the שר האופים seems to be backwards. What was their original crime? The שר המשקים failed to prevent a fly from entering the cup of the Egyptian King, and the שר האופים failed to notice a tiny needle which had fallen into the King’s bread. The crime of the שר המשקים is substantial; he literally handed the King a cup of wine with a fly in it! It’s not normal for the baker to hand the bread directly to the King. Even though there ended up being a needle in it, it’s not as much of an affront to the King’s honor. In fact, the bread might not have even reached the King’s plate. Why was the one with the smaller crime punished with death, and the other reinstated? Also, why such an extreme ruling? Pharaoh could have simply fired them both. Why was this considered a capital crime? The Torah even calls their crime a sin; it’s surprising to call simple lack of attention a sin.
A possible explanation is what was going on behind the scenes. The two ministers, due to their baseless hatred for one another, were brazen enough to try to get the other in trouble. The שר המשקים put a needle in the bread, and the שר האופים put the fly in the King’s cup. From this we see the sin of the שר האופים was much greater; he caused the שר המשקים to give the King a cup with a fly in it! That’s why he was sentenced to death. This is unlike the שר המשקים. Although putting the needle in the bread was a crime, there was a chance the King would have never even had that piece of bread. In the end, he was reinstated.
A third explanation brought for the four cups of wine is they correspond to the four exiles that were destined to fall upon the Jews. The meaning behind this is clear. It makes sense to drink a cup of wine as celebration for every salvation that is given to us, as the verse states: כוס ישועות אשא, the cup of salvations I will raise [to drink]. Since the four exiles will have four redemptions, we drink four cups of wine.
It’s clear that the reason for most of the exiles is the sin of baseless hatred. This is what the story of Yosef in prison is alluding to. Yosef was innocent from the sin of baseless hatred. The dream of the שר המשקים and its interpretation teaches us that just like baseless hatred caused them to be thrown in prison, the Jewish people’s baseless hatred of each other caused their four exiles. Each of these exiles deserves its own cup of wine to celebrate the salvation that was given to us, and the salvation that is yet to come. From all of this it’s clear why we don’t mention the four cups of wine in the מה נשתנה, the four questions. The four cups of wine don’t represent the best of the Jewish people, rather they signify a fault. There has been baseless hatred in the past, which have caused endless pain throughout the millennia. Let’s work together to eradicate baseless hatred, and look forward to the final redemption.
Good Shabbos and Chag Kasher VeSameach!
 Based on the Leil Shimurim commentary on the Passover Haggadah by the Aruch HaShulchan
 Literally: what. The Leil Shimurim comments that if it meant why it should have said למה. “What” is meant to denote astonishment, such as מה רבו מעשך השם, how great are your wonders Hashem, from Psalms 92:6
 Passover Haggadah, source from Pesachim 10:4
 First the karpas (a tiny vegetable such as a slice of cucumber, carrot or potato) into salt water and later the marror into the charoses
 See Bereishis Rabbah 88:5 and Yerushalmi Pesachim 10:1
 Exodus 6:6-7
 Genesis 39:12-40:23
 Three were mentioned by the minister and one by Yosef. The Midrash and Yerushalmi (loc. cit.) both combine these into four. However, for some reason Rashi to Pesachim 108a s.v. ארבע כוסות only counts the 3 times that were stated by the minister, and says the fourth cup is simply from the obligation to recite birkas hamazon over a cup of wine. Rav Asher Weiss doesn’t understand this Rashi, since kiddush also requires a cup of wine, by this logic we should say there are five cups of wine: three from the minister’s expressions and two from kiddush and bentching. Or if kiddush is included in what the minister said, why not benching as well, and say there are only three cups? See as well Rashi to Pesachim 99b s.v. ארבע כוסות
 Yirmiyahu 31:14
 Cf. Eicha Rabbah Pesikta § 24 which only mentions the forefathers Avraham, Yitzchak, and Yaakov, as well as Moshe, crying and praying to Hashem alongside Rachel, with no mention of the other foremothers
 See the prophets Amos 1:11, Ovadiah 1:1 and 1:12, and Psalms 137:7 who describe this baseless hatred
 Even though the verse with Rachel crying is referring to the Babylonian exile, the Leil Shimurim seems to switch the focus of the discussion to Edom and its descendants, including the nation of Amalek
 See Genesis Chapter 37. It’s not clear to me why it’s considered baseless hatred, the verses explicitly describe the source of their feelings towards Yosef
 This also explains why King Shaul and Queen Esther, descendants of Binyamin, were specifically chosen to combat Amalek and no one from the other tribes. It also explains the concept of Moshiach ben Yosef paving the way for Moshiach ben Dovid
 Rashi to Genesis 40:1, quoting Bereishis Rabbah 88:2
 See note 5
 Psalms 116:13
 Yoma 9b
 It’s now evident that the 3 opinions listed in the Midrash and Yerushalmi (loc cit.) are really all giving the same message, just from different vantage points: 1) the message of baseless hatred from the story of Yosef which created the need for 2) the four expressions of redemption from the 3) four exiles