Esther 5:6, Question 1. Why does the verse specify that this is a drinking party?

ו וַיֹּאמֶר הַמֶּלֶךְ לְאֶסְתֵּר בְּמִשְׁתֵּה הַיַּיִן מַהשְּׁאֵלָתֵךְ וְיִנָּתֵן לָךְ וּמַהבַּקָּשָׁתֵךְ עַדחֲצִי הַמַּלְכוּת וְתֵעָשׂ

6. And the king said to Esther in the drinking party, “What is your request and it will be given you, and what is your petition? Until half of the kingdom, and it will be done.”

  • The Ben Ish Chai writes that this is not the first wine party in Megillas Esther. In fact, after Haman and Achashverosh sign the decree meant to threaten Jewish existence, the verse (Esther 3:15) writes that they drank together. At that party something happened that this party will help to undo. Besides this, the verse there says that the city of Shushan was left bewildered. Among the reasons for this confusion is that the Jews were not privy to the content of the decree. They were left unclear as to the veracity of the inevitable rumors that this decree intended their demise. The Ben Ish Chai writes that this party, providing the tikkun to the previous party in the manner of “zeh l’umas zeh,” will leave no confusion.
  • The Kotzker Rebbe writes that we are all supposed to remember that H-Shem listens to our requests not only when we are praying in a holy environment, but also when we are sitting at a table, eating and drinking in the measured way in which we are instructed. This is why H-Shem, the King in our verse tells Esther, who represents the Jews, that He will do what she requests. This is one reason why we request in Birkas HaMazon a number of things besides sustenance.
  • The Dubno Maggid adds that King David unified his requests with his goals (see Tehillim 27:4). The Talmud (Avodah Zara 19a) says that one should do mitzvos for their own sake. This is what Dovid was doing. This is particularly relevant in the area of prayer because the Talmud (Brachos 20a) calls Yerushalayim “the hill towards which all mouths are directed.” We all have different mouths – or requests – but they are all for the same goal. Everything we want should be for the sake of our personal relationships with H-Shem.
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Esther 3:5, Question 1. Why does Haman wait until he sees this to become angry?

ה וַיַּרְא הָמָן כִּיאֵין מָרְדֳּכַי כֹּרֵעַ וּמִשְׁתַּחֲוֶה לוֹ וַיִּמָּלֵא הָמָן חֵמָה

5. And Haman saw that Mordechai was not kneeling and bowing to him, and Haman became filled with fury.

  • As human beings, things often do not register until we actually see them for ourselves. In Acharei, after the death of two of Aaron’s sons, H-Shem teaches the laws of the Yom Kippur service. Explaining the Torah’s reason for relating these two events in his commentary there (Vayikra 16:1), Rashi brings a parable from a Midrash (Toras Kohanim, Parshas 1:3-4) that has one doctor ordering a patient to keep a certain regimen. Then, a second doctor comes in to order that patient to keep the very same regimen, but with the precaution that he should do so in order not to die as did so-and-so. This second doctor is more convincing because his using the story of so-and-so as a cautionary tale made the reality of the threat to his life more concrete for the patient.
  • Malbim points out that Haman was observing Mordechai at this point. Apparently, hearing the words of these men caused Haman to pay attention to the behavior of the people around him. Perhaps we can say that he simply did not believe them. The Talmud (Kiddushin 70a) teaches a famous dictum: “kol haposel b’mumo posel” (“all who invalidate, in their own negative trait invalidate”). In other words, people judge others as reflections of their own characteristics. Being a dishonest, evil person himself, Haman thought everyone was dishonest, and simply would not accept the words of anybody.
  • The Midrash (Esther Rabbah 7:9) quotes Tehillim (69:24) “the eyes of the evil one are darkened.” What evil people see brings them to their ultimate destruction. The Midrash continues to bring numerous verses of evil people seeing something that causes their downfall. The opposite is true for the eyes of the righteous, because they raise them up. The Dubno Maggid asks why vision is the focus of this Midrash. That certainly cannot be the only difference between the good and the evil! He answers that we were all born spiritually equal, and evil people became such by looking at things in the wrong perspective, and thus making physical choices that negatively impacted their spirituality. In our verse, for example, Haman is upset that Mordechai is not bowing to him – whereas he would just as easily have focused on the positive fact that 99.99% of the population was bowing to him. Instead, he focused on the negative – that one person was not bowing to him. That negative focus is the trademark of the evil.

Esther 1:19, Question 5. What does the phrase “better than her” indicate in relation to Vashti?

Certainly, one would expect the next queen to learn from the example of her predecessor and be very careful to always listen to the king. In pointing out that this phrase is a definite allusion to Esther, the Midrash (Esther Rabbah 4:9) states that Scripture uses the very same phrase of “better than you” (Shmuel 1 15:28, albeit in the masculine form) in both the removal of kingship from Esther’s ancestor, Saul, as well as the beginning of Esther’s ascension to the throne here. The Dubno Maggid explains that the Midrash is demonstrating how H-Shem allows a characteristic that had a seemingly negative aspect in one instant to have the exact polar opposite effect elsewhere. This was the particular aspect of H-Shem’s hashgacha (mida kineged mida) that Yisro praised in saying “[the Egyptians’] own plots turned against them” (Shemos 18:11, see Rashi there). Rav Chaim Volozhin in Nefesh HaChaim (1:7) elaborates on the mechanics of this theme.

Esther 1:8, Question 3. Who is being referred to in the phrase “man and man?”

  • The Talmud (Megillah 12a) learns from the fact that each is called a “man” in the Megillah (Esther 2:5 and 7:6), that this verse is referring to Mordechai and Haman. Haman being at the party makes sense according to the idea that he intended to convince the Jews to sin. What, however, would Mordechai be doing at this party? Ri Pinto explains that Mordechai forced himself to come to the party he has erstwhile been railing against to make sure the Jews would not be forced to consume forbidden foods and drinks. The Dubno Maggid explains this with a parable regarding a boy who has a doting father and a stingy stepmother. One day, the boy becomes sick, and his doctors tell the father to make sure the boy does not overindulge in food until he regains his strength. Later, when the boy is about to eat what the father considers too much, the father quickly takes the food from him. The boy cries, “Father, why are you suddenly behaving like my stepmother in not allowing me to be happy?” The father answers, “True, we may be acting towards you similarly now, but it is for very different reasons.” Similarly, the Talmud has Mordechai and Haman acting similarly towards the Jews at the party, but with diametrically opposing intentions. 
  • Why does the Talmud here have to stray so far from the simple explanation that “each person” was to be satisfied? Maharal in Ohr Chadash cites the Midrash (Esther Rabba 2:14) that has H-Shem saying of Achashverosh that it was haughty of him to try to satisfy everyone. After all, H-Shem says,

        I am not able [aside from bypassing the laws of nature] to satisfy all my creations simultaneously. And yet you seek to do according to the wants of [every] man and man?! It happens in the world that two men seek to marry the same woman. Can she marry both? Either this one or that one! Also, two ships can be docked with one hoping for a northern wind, and the other waiting for a southern wind. Can one wind satisfactorily carry them both? Either this one or that one!

In other words, the Maharal continues, trying to satisfy everyone at the feast was another attempt by Achashverosh to usurp H-Shem’s Kingship by doing something even He does not do – satisfy everyone simultaneously. Perhaps, since nature is set up in a way as to make it impossible to satisfy “each person,” the Talmud needs to learn “man and man” as specific groups, or even persons, who could theoretically be satisfied at the same time.

Esther 1:6, Question 5. Why does the Megillah go into these details about Achashverosh’s party at all?

  • According to the Vilna Gaon, one of the reasons to include these unusually specific details is the Torah’s desire to demonstrate how grand an earthly party can be. The Mishnah in Avos (4:22) states that the pleasure of the future world is unimaginably greater than this world’s greatest pleasure. Without this description, how would we ever know how great this world’s pleasures can be?
  • In the view of the Dubno Maggid, the Jews who attended the feast did so on purpose. He quotes the Midrash (Esther Rabba 2:5) that portrays a dialogue at the feast wherein Achashverosh asks the Jews, “Is your G-d capable of doing more than this for you in the end of days?” The Jews respond with an obscure quote from Yeshayahu (64:3), “[Since forever, nobody has listened, nor heard,] nor eye has seen, Elokim, (זולתך) except for You, what You will do for [someone] who waits for You.” There being countless verses in TaNaCh that hint to descriptions of the World to Come, how is this verse the best answer to the question? To explain, the Dubno Maggid tells a famous parable describing a rich man with an angry wife. Throughout his day, she annoys him with constant bickering. Finally, a day comes when she has to take care of something out of town for a few days. On the first day of her absence, the man asks his servant to prepare a delicious meal and serve his best wine. He eats and drinks, and truly enjoys his moments of peace. He orders a similar bill of fare for the following day. Surprisingly though, the man’s wife returns from her trip early, just before his feast. She joins him for the meal and asks him afterwards if the food was as good the previous day. He answers, “Honestly the food was better today, but it was easier to enjoy yesterday when I could eat it in peace.” The Jewish response to Achashverosh is similar in that they hinted that their future reward will at least be superior in that it will be זולתך, which can also be translated as “without you,” meaning Achashverosh. For obvious reasons, they had to choose their words carefully so that their answer would not be taken as the insult it naturally was.