Esther 8:3, Question 1. Why does Esther perform all of these actions?

ג וַתּוֹסֶף אֶסְתֵּר וַתְּדַבֵּר לִפְנֵי הַמֶּלֶךְ וַתִּפֹּל לִפְנֵי רַגְלָיו וַתֵּבְךְּ וַתִּתְחַנֶּןלוֹ לְהַעֲבִיר אֶתרָעַת הָמָן הָאֲגָגִי וְאֵת מַחֲשַׁבְתּוֹ אֲשֶׁר חָשַׁב עַלהַיְּהוּדִים

3. And Esther added and spoke before the king. And she fell before his feet, and cried, and pleaded with him to annul the evil of Haman the Aggagite and his intentions that he intended on the Yehudim.

  •  The Maharal is troubled by the verse’s use of the word vatosef (“and she added”) when it does not initially seem that there is any conversation that is being continued here. He answers that this is a continuation of the previous verse in which Esther appointed Mordechai, seemingly verbally, as master of Haman’s estate.
  • M’nos HaLevi notes that the Talmud (Makkos 10b-11a) teaches that daber, the root of word vatidaber (“and she spoke”) implies a harsh language. He explains that Esther was speaking in a forceful and direct manner to the king, saying that Haman lied to him. She then regretted her boldness, and fell pleading for mercy.
  • According to the Malbim, Esther performs all of these actions because she tried various methods to convince Achashverosh – rhetoric, and logic, and emotion. As is well-known, when logic fails, the emotional appeal can still be effective.
  • As the M’nos HaLevi points out, the Talmud (Brachos 32b) teaches that since the time the Beis HaMikdash was destroyed, only the gates of tears remain open.
  • In a famous comment on this verse, the Vilna Gaon teaches in the name of the Zohar that genuine crying always comes from the heart, and cannot be artificially manufactured. He also connects Esther’s behavior in this verse to various stages of the Jew’s regular prayer routine. He writes that vatosef (“and she added”) is a reference to Pesukei Dezimra (introductory verses of praise) because the Talmud (Brachos 32a) teachers that these were added by the Rabbis to help people concentrate during Shemoneh Esrei; vatidaber (“and she spoke”) is a reference to Shema (“verses in which we accept the authority of H-Shem”) because the Talmud Yerushalmi (Brachos 9a, 9b) teaches that the Shema has references to the Ten Commandments, the Asseres HaDibros, vatipol (“and she fell”) is a reference to nefilas apayim (“putting down the face,” or Tachanun), vateiv’k (“and she cried”) is a reference to tefilla (“the silent prayer, or Shemoneh Esrei”), and vatit’chanen (“and she pleaded”) is a reference to Elokai Nitzur (the additional prayers after tefillah). Esther’s act of pleading before the king, was also her pleading before the King of kings.
  • The Dena Pishra writes similarly that the verse references the king because Esther was really praying to H-Shem to spare the Jews.
  • The Ginzei HaMelech writes that Esther did all of these actions because she saw the cause of Achashverosh’s previous behavior as passion due to anger. Now that she saw him calm down, she was concerned that he would return to his old, anti-Semitic self. She was really risking her life because his anger could have returned at any moment.

Esther 8:4, Question 2. Why does Esther stand?

  • Continuing his thoughts on the previous verse, the Vilna Gaon writes that Esther’s rising up alludes to the end of the morning prayer service, and her standing alludes to the kaddish prayer.

  • Similarly, the Dena Pishra explains that Esther was standing here because she was pleading before H-Shem, and this is why the verse refers to Him as King.

  • The Shelah writes that we should stand in prayer before H-Shem the same way we do before a human king.

  • R’ Moshe Feinstein would famously stand still during prayer instead of shukeling back and forth, as many do. The source of this custom was an incident in which, as a rabbi in communist Russia, he was called before the police commandant. He recalled that one of the most frightening events of his life was standing there, stock still, unable to move. Realizing that one is standing before an authority should cause one to avoid any movement.

Esther 6:12, Question 1. Why does the verse emphasize that Mordechai returned to the king’s gate?

יב וַיָּשָׁב מָרְדֳּכַי אֶלשַׁעַר הַמֶּלֶךְ וְהָמָן נִדְחַף אֶלבֵּיתוֹ אָבֵל וַחֲפוּי רֹאשׁ

12. And Mordechai returned to the gate of the king. And Haman was propelled to his house mourning, and with a covered head.

  • It seems doubly strange for the verse to say Mordechai returned to the palace, when our commentary on the previous verse made clear the Haman found Mordechai in the house of study. According to the Talmud (Megillah 16a) and the Midrash (Esther Rabba 10:6), the verse emphasizes that Mordechai returned to the king’s gate instead of into because Mordechai returned to wearing sackcloth and fasting.
  • Rashi’s explaining that Mordechai returned to mourning seems to not be his pashut pshat, simple explanation.
  • The Maharsha clarifies that Mordechai could not enter the king’s gate wearing sackcloth because of their rules of propriety in those days, so he could only come as far as the gate, itself. Therefore, Mordechai, having been mourning in sackcloth for the last several days could not be said to be returning to a place where he could not have previously been.
  • R’ Avigdor Bonchek explains that being paraded on a horse emboldened Mordechai to defy Achashverosh’s law by going to gate in sackcloth.
  • The Targum writes that Mordechai returned to serving on the Sanhedrin at this point, a position that is described in TaNaCh (see Bireishis 19:1, Devarim 21:19, Ruth 4:1) as being positioned “at the gate.”
  • The Midrash (Shemos Rabba 38:4) teaches that the verse says Mordechai returned because he is humble. There is a humility in accepting one’s place, as is said of Avraham whom the Torah (Bireishis 18:33) describes as having “returned to his place” after speaking with H-Shem.
  • R’ Henoch Leibowitz notes that the Torah (Devarim 30:8) promises us that H-Shem will return us to our Land only after we suffer from our enemies. Rav Leibowitz explains that the lesson is that a person’s prayer in times of rescue should be equal in power and intensity to that with which one prays in times of troubles. The very purpose of our troubles is to increase our attachment to H-Shem. The proper method for this is to follow Rabbeinu Bachya’s advice (on Shemos 2:23) when he says that one’s prayer is the most intense in times of difficulty and that, therefore, it is incumbent on a person to remember that feeling of intensity, and bottle up that feeling of pain in order to pray strongly in the brighter future that the troubles do not return. At our most desperate, we should try to encapsulate the emotion to use in better times.
  • He quotes R’ Naftoli Tropp, the Rosh Yeshiva of the Chofetz Chaim’s yeshiva in Radin writes that a famous piyut said on Yom Kippur calls us all dalim, poor. Even the rich should recall that all is H-Shem’s and they only have their riches only by the grace of G-d.
  • The Yosef Lekach writes that Mordechai usually wore sackcloth during davening, and then changed for court. At this point, Mordechai did not change because he felt his prayers were unsuccessful, and not answered. This is because his riding on a horse did not manifestly spell out the redemption of the Jews. The Jews were still threatened.
  • Rebbetzin Heller points out that, being G-d focused, Mordechai didn’t care if Achashverosh loved or honored him. This event did not change Mordechai’s humility.
  • The Sfas Emes writes that Mordechai still felt guilty about causing the threat to Jewish existence by refusing to bow down to Haman. True teshuvah comes from the feeling of being unworthy of kindness from H-Shem. He concludes that one should never be too confident in this.
  • The Iyun Yaakov points out that, on the political side, Mordechai had anticipated using his saving Achashverosh’s life as leverage when begging Achashverosh to save the Jews – not just a pony ride around town. Disappointed by the loss of his ace in the hole, Mordechai’s only remaining means to save the Jews is to pray to H-Shem.
  • The Ohel Moshe quotes the Brisker Rav, R’ Yitzchak Zev HaLevi Soloveitchik that in his reporting the goings-on to Esther earlier (Esther 4:5-16), Mordechai was unwilling to get out of his sackcloth for even one moment and even requiring Hasach as an intermediary because prayer and emunah are the main tools for salvation.
  • The Ohel Moshe also brings R’ Yehonason Eibshutz who quotes the Talmud (Brachos 5b) that a prisoner does not free himself. Somebody else needs to help somebody out. Similarly, Mordechai, once he sees himself rescued, returned to pray for the other Jews. Similarly,
  • R’ Dovid Bleicher of Novordok notes that Mordechai had his own needs met, but kept praying for the Jews because he had worked on himself to feel as if he was still under the threat of death.
  • The Midrash (Esther Rabba 6:12) states that a true Jewish leader does not stop fasting until the prayers are answered.
  • The Maharal notes that Mordechai was not satisfied by this honor because Achasherosh did not come to thank him, himself. He had no reason to think that Achashverosh felt actual gratitude. After all, as R’ Elie Munk points out in his commentary on Chumash (Vayikra 7:30), of all the offerings, the only one which the Torah describes as having to be brought “by his own hands” is the shelamim (peace offering) because it is brought as a way to thank H-Shem, and “when expressing one’s gratitude, it is proper to do it personally.”
  • Parenthetically, he also quotes this as the reason brought by Abudraham for the congregation to say the blessing of Modim (thanksgiving) during the repetition of the Amidah prayer, since the congregational leader cannot express the gratitude of another person.
  • The Maharal also says in a few places (Nesivos Olam) that simcha (joy) comes from shleimus (completeness). Here, too, Mordechai cannot be content since the Jews are still under the threat of annihilation, and are thus incomplete.
  • Perhaps the simplest explanation to why Mordechai returned to his place can be gleaned from a story told about R’ Yechezkel Abramsky. While discussing Megillas Esther with his rebbetzin, he asked her what Mordechai could have been thinking while riding on the horse. She answered, “This type of foolishness is for drunkards. I wish this will be over soon, so I can return to learning Torah!”

Esther 6:11, Question 1. Why does the verse repeat the details of Haman’s actions?

יא וַיִּקַּח הָמָן אֶתהַלְּבוּשׁ וְאֶתהַסּוּס וַיַּלְבֵּשׁ אֶתמָרְדֳּכָי וַיַּרְכִּיבֵהוּ בִּרְחוֹב הָעִיר וַיִּקְרָא לְפָנָיו כָּכָה יֵעָשֶׂה לָאִישׁ אֲשֶׁר הַמֶּלֶךְ חָפֵץ בִּיקָרוֹ

11. And Haman took the clothing and the horse, and dressed Mordechai. And he rode him in the street of the city. And he called before him, “So will be done to the man for whom the king desires his glory.”

  • Perhaps the verse’s repetitious detailing of Haman’s actions alludes to more information about the story, as both the Talmud (Megillah 16a) and Midrash (Esther Rabba 10:4) detail in their own ways.
  • According to both sources, when Haman took the clothing and the horse to Mordechai, he found the sage teaching the laws of kemitza, the three fingersful amount of barley flour the kohanim would gather for the Temple offerings (Vayikra 2:2 and elsewhere). Rashi explains that Mordechai was discussing this topic specifically because it was the 16th of the month of Nissan, the beginning of the cycle of omer offerings.
  • According to the Ginzei HaMelech, they were specifically learning about the Omer in order to earn the merit to return to Eretz Yisroel in order to properly fulfill that mitzvah.
  • When Mordechai sees Haman coming, Mordechai warns his students to run away, but his students refuse. The Midrash has them respond that their fate should be the same as their rebbe’s. Mordechai wraps himself in a tallis, and begins to pray. While sitting and waiting for Mordechai to finish, Hamans asks the students what they are learning. They cry to him about missing the Beis HaMikdash, and explain that we would have had the kemitza of the mincha offerings to atone for us. Haman responds that this little three fingersful amount of flour pushed off the power of 10,000 loaves of silver.
  • A slight variant in the Midrash is that Haman is surprised that the worth of barley needed for kemitza was so little.
  • When Mordechai concludes praying, he tells Haman, “Wicked one! A slave who acquires something, does not his master own it?” In other words, since Mordechai was his master, the 10,000 loaves of silver Haman had offered Achashverosh for permission to destroy the Jews (Esther 3:9) did not even belong to Haman to give away.
  • Haman tells Mordechai to get up and get dressed and ride on the king’s horse. Mordechai tells him he must first have a haircut and bath before wearing the king’s crown. Since Esther had made a rule that all the barbershops and bathhouses were to be closed that day, Haman had to bathe Mordechai himself, and got scissors from his house to cut Mordechai’s hair.
  • According to the opinion that this was not the second day of Yom Tov, the Maharitz Chiyas writes that the Talmud (Moed Katan 13b) and Halacha (Shulchan Aruch Orach Chaim 531:4) allow a person to take a haircut on Chol HaMoed (if this was not, indeed, the second day of Yom Tov) if it was impossible to get earlier, as for a prisoner released on Chol HaMoed.
  • Furthermore, the Derash Avraham writes that Mordechai could take a haircut and bath even on Yom Tov in order to save lives.
  • The Vilna Gaon asks how Esther could risk so much in having the bathhouses and barbershops closed. After all, she could not have had enough advanced notice to know this event would occur. Furthermore, Esther risked giving up the guarded secret of her Jewish background.
  • R’ Yehonason Eibshutz answers that this was the second day of Yom Tov, so Esther calling Jewish barbers to stay home for Halachic reasons (Shulchan Aruch Orach Chaim 495:2). Esther felt she needed to strengthen this Rabbinic law because the Persian Jews were generally reluctant to follow Rabbinic decrees.
  • While cutting the hair, Haman was groaning. Mordechai asked, “Why are you groaning?” Haman responded that someone like himself, who is so important to the king, should not be degraded into the post of barber. Mordechai told him, “Wicked one! Were you not a barber in Kartzum for 22 years?”
  • The Beirach Yitzchak asks about the significance of the length of time. He answers that the Rambam (Mishneh Torah, Hilchos Melachim 1:6), in his list of people disqualified from royalty, includes a barber. In his commentary on the Mishneh Torah, Rav Yosef Karo in Kesef Mishnah explains that barbers in bygone days were responsible for administrating numerous medical treatments, many of which were repulsive and unseemly (http://www.history.com/news/history-lists/7-unusual-ancient-medical-techniques).
  • The Kesef Mishnah further limits this restriction to barbers who do this as a profession, not just a hobby or as a favor for someone. Therefore, answers the Beirach Yitzchak, Haman’s being a barber for such a long time indicates that it was his profession, and he could not weasel out of the fact that he was not fit for the royalty to which he aspired.
  • Furthermore, adds the Ginzei HaMelech, Mordechai was telling Haman that, had he remained contentedly a barber in Kartzum, his life would continue in relative peace. However, now that he had been elevated and become corrupted by power, Haman’s life would end tragically. When it was time to get on the horse, Mordechai was too weak from fasting, and had to climb on Haman’s back to alight on the horse.
  • Since the fast was supposed to last for three days (Esther 4:16), the Chiddushei Rashash writes that Mordechai was still fasting on this, the fourth day, because he added an extra private day of fasting for himself. The reason may be that he felt responsible for the Jews’ plight since he instigated Haman’s hatred by not bowing to him (Esther 3:5).
  • Given the opportunity, Mordechai kicked Haman in the posterior. Haman complained that it says in the TaNaCh (Mishlei 24:17) that one should not rejoice over the downfall of one’s enemies. Mordechai responded that this is true regarding Jews. However, regarding gentiles, the Torah (Devarim 33:29) writes that we can rejoice. Ginzei HaMelech wonders why it seems from this story that Mordechai and Esther appear to be working together to increase Haman’s humiliation. The answer could be, as the Ramban (to Bireishis 12:6) writes, some physical action is always necessary for us to fulfill a Divine decree. Therefore, Esther and Mordechai are performing physical actions to acquire something from the spiritual events then occurring.
  • Then, Haman begins to lead Mordechai on a horse through the streets of Shushan. An earlier Midrash (Esther Rabbah 7:7) points out that all of Rachel’s descendants are equal; just like Yosef rode in Pharoah’s second chariot through the streets of Mitzrayim (Bireishis 41:43), so too Mordechai.
  • The Midrash (Esther Rabba 10:5) details what everyone was saying during this procession. Mordechai was saying the verses (Tehillim 30:1-4) which praise H-Shem for elevating him, and not allowing his enemy to defeat him. Mordechai’s students were singing the next verses (ibid. 5-6), praising H-Shem for the change in the course of history that He controls for the sake of His righteous followers. Haman was saying the next verses (ibid. 7-8) bemoaning his fall from power. Esther said the next verses (ibid. 9-10) praying for success in her mission to save the Jews. The rest of the Jewish people were saying the next verses (ibid. 11-12), celebrating the changing tide from fear to jubilation.
  • 27,000 young men led this procession, carrying pillows and golden cups and repeating Haman’s words that this is the reward for the man whom the king wishes to honor. The M’nos HaLevi explains that the purpose of these 27,000 young men was to continue this message after Haman’s voice inevitably gave out after a while.
  • Haman’s daughter, who was on a rooftop, dumped her chamber-pot upon her father, thinking he was Mordechai.
  • According to R’ Mendel Weinbach, the reason she had a chamber pot with her on the roof is that Haman had engineered Vashti’s end and the ensuing beauty contest with the goal of having the king marry his daughter. To avoid her becoming the queen, H-Shem cursed her with chronic diarrhea, so she hid from people on roof tops, always with her chamber pot. As Haman looked up to see who had done that, his daughter became ashamed, and she jumped off the roof.
  • The Ben Ish Chai writes that she did not recognize her own father was due to his voice becoming hoarse.
  • The Einei Yitzchak writes that another reason she may not have recognized her father is that Haman may have switched clothes with Mordechai in order to make sack-clothed Mordechai more presentable, and to ironically lessen his own embarrassment.

Esther 6:10, Question 3. Why does Achashverosh stress that Mordechai sits at the gate of the king?

  • The Yad HaMelech points out that Achashverosh stresses that Mordechai sits at the king’s gate in order to allay Haman’s concern that honoring Mordechai may be beneath his dignity. This is not to imply that Achashverosh suddenly cares about Haman’s honor; in fact, if Haman were to honor somebody lowly, that could reflect poorly on Achashverosh, his king.
  • According to the Talmud (Megillah 16a), Haman attempted to stall by pretending to not know which Mordechai Achashverosh had in mind, and the king had to narrow down the identity of this particular Mordechai.
  • The Maharal says that the reason Haman’s advice of giving the honoree the crown (Esther 6:8) is not mentioned again is because the king should ordinarily give these items, himself. However, in the case of this person who is a major adviser who “sits at the gate of the king,” Haman can bring him the crown.
  • The Ginzei HaMelech notes that Achashverosh here does not describe Mordechai as one “who sits at my gate,” but rather the “gate of the king” because he is alluding to the fact that Mordechai sits at the gate of the King, H-Shem. Earlier (Esther 2:5), when Mordechai was referred to as the “son of Kish,” the Talmud (Megillah 12b-13a) understood that to mean that he knocked (“hikish”) at the Gates of Mercy. His praying therefore qualified him to be called one who sits at the gate of the King.

Esther 5:14, Question 3. Why did Haman’s advisers advise him to go to the king in the morning?

  • The Malbim writes that they wanted Mordechai hanged in the morning because that is when public executions were performed in order to show the strength of the monarchy.
  • The Ben Ish Chai writes that Zeresh was, in effect, telling Haman that Mordechai was in prayer at that time, he wouldn’t be aggravated by the sight of him.
  • The Maharal says that morning represents geulah (redemption). This is why the very next verse (Esther 6:1) begins the positive upswing of Megillas Esther.
  • R’ Yehonasan Eibshutz quotes the Midrash Abba Guria that Zeresh wanted Mordechai to be killed during the time of Shema. That way, Mordechai would be unable to connect geulah to tefillah (prayer)1, which the Talmud promises would have otherwise protected him (Brachos 9b).

1This is a Halachic concept (Shulchan Aruch Orach Chaim 66:7, Mishnah Berurah ibid., sub-paragraph 33) that forbids any interruption between the morning prayer ending in “ga’al Yisroel” (“Savior of Israel”) and the Amidah.

Esther 5:8, Question 3. Why is the next party specifically tomorrow?

  • According to Rebbetzin Tzipporah Heller, Esther planned for the next party to specifically occur the next day in order to “intensify the effect of her plan.” This would make the tension between Achashverosh and Haman more palpable.
  • According to Rav Dovid Feinstein, this immediacy of the next party would pique Achashverosh’s curiosity, and keep him in suspense. Besides this, it is important to remember that the Jews were already fasting for two straight days, and Esther had asked the Jews to fast for three days, culminating in the next day. The merit of their fasting will both spiritually and psychologically support Esther’s efforts at that day’s feast.
  • According to R’ Meir Arama, pushing the next party into the next day was Esther’s attempt to stall her inevitable request from the king. Without a clear sign from H-Shem, she was confused if she should fight Amalek using Yaakov’s method, or Moshe’s. Yaakov (Bireishis 32:9) attempted to defeat Eisav, Amalek’s ancestor, through gifts. Moshe (Shemos 17:8-13) utilized prayer and war against the nation of Amalek.
  • The Yalkut Shimoni (1056) writes that Amalek is defeated machar, tomorrow. This is because Moshe, at the first national encounter against Amalek, said “tomorrow I will stand on top of the mountain” (Shemos 17:9).
  • The Maharal explains that Amalek does not recognize an other, a tomorrow. Amalek causes religious doubt (the Hebrew word safek has the same gematria as Amalek.) by forcing the brain to consider only one approach to a Torah dilemma; if that approach does not work, there can be no other way to look at the topic.
  • Perhaps another reason why the next day was so critical to Esther’s plan can be gleaned from the gematria of the Hebrew word machar, (“tomorrow”) (40+8+200=248). This is the same number as the positive commandments (Makkos 23b-24a), which themselves correspond to the major bones and sinews in a man1. Therefore, one more day of the Jews performing positive mitzvos and teshuva will help Esther. Perhaps this is the reason why the Midrash later notes that Haman was advised to approach Achashverosh specifically baboker (“in the morning”) (Esther 5:14), which the Midrash says is the time of reading the Shema.

1The significance of this number is also the reason for adding three words to the twice daily recitation of the Shema, which would only have 245 words alone (see Shulchan Aruch Orach Chaim 61:3 and Mishnah Berurah 61:6).