Reaching the greatest heights through regretting sin
חייב איניש לבסומי בפוריא עד דלא ידע בין ארור המן לברוך מרדכי
A person is obligated to get drunk on Purim to the point that they don’t know the difference between “Cursed is Haman” and “Blessed is Mordechai”
Everyone is familiar with the concept of getting drunk on Purim. Our Sages even seem to say that a person is obligated to get drunk on Purim. This begs the obvious question: How could our Sages obligate such a repugnant thing? Our scriptures are full of descriptions of the evils of drunkenness, and it is known to all that it causes people to stumble in their behavior. Why would the day of Purim be any different? This is a question that many struggle with. One suggestion is that it’s to commemorate the fact that all the miracles of Purim occurred through the drinking of wine. Vashti was sentenced to death because Achashverosh was drunk, allowing Esther to become the queen. Haman’s downfall occurred during a wine drinking party. Nevertheless, this doesn’t seem to be a satisfactory explanation. Why should this commemoration be enough to justify something so vile?
As her main attempt to save the Jewish people from annihilation, Esther planned a drinking party. Regardless of her intentions, her plan was to invite Achashverosh and Haman to the party, and inform Achashverosh that Haman was plotting to wipe out the Jewish people. We see that her plan worked, as that party was the catalyst to Haman’s downfall. However, how could Esther have a drinking party as part of her plan? Furthermore, how could this plan have succeeded? Our Sages tell us that the sin which prompted Haman’s decree to exterminate the Jewish people was because they took part in Achashverosh’s party. The Megillah begins with the 180-day feast Achashverosh threw, and Mordechai warned the Jews against going. Ignoring his wishes, they went anyways, and ate and drank. This sin was so severe that the resulting decree was to wipe out the entire Jewish people, every man, woman, and child. How then could Esther use a drinking party to annul the decree if it is the very thing which created it in the first place? How could it have any merits that could make it successful?
Hashem, through His Prophet Shmuel, instructed Shaul, the first King of Israel, to destroy the enemy Amalek. The entire nation, including their livestock, was to be wiped out for their evil deeds. Shaul successfully launched a siege against the nation, and all that remained was their king, Agag, and their livestock. Instead of destroying them, Shaul decided to keep them alive. He wanted to use the livestock for offerings for Hashem. When Shmuel came to see the results of the siege, he catches Shaul with the imprisoned Agag, and all the livestock. What did King Shaul say to Shmuel? You would think that he would admit that he didn’t follow Hashem’s command. He could have apologized, or admitted that he had a momentary lapse of judgement. He did the exact opposite. He said הקימותי את-דבר יקוק, I have upheld the word of Hashem. He had the gall to claim that he followed Hashem’s command. Didn’t he realize he sinned?
Our Sages tell us a surprising fact. When Hashem first presented the Torah to us, He had to put a mountain over our heads for us to accept it. It was only after the Purim story that we were so grateful as a nation that we accepted the Torah willingly. Until that time, if we ever didn’t follow the Torah, we always had the excuse that we didn’t willingly accept it in the first place. Really? How can we understand this? The Jews just saw the Ten Plagues in Egypt. They saw the splitting of the sea. They saw the Divine Revelation at Mount Sinai. They didn’t want to accept it? Furthermore, they eventually entered the land of Israel. The Jews conquered all of their enemies. They built the Temple. There were daily miracles in the Temple. All of this time, it didn’t occur to them to accept the Torah willingly? Only in the days of Achashverosh? What changed?
There’s a couple of oddities in the Megillah itself. One, is Mordechai tells Esther that if she chooses not to reveal her identity to Achashverosh, imploring him to spare her people, no problem. Salvation will come to the Jewish people regardless. However, she should know that if she doesn’t bring it about, her and her father’s house will be destroyed. What does Mordechai mean? What does her father’s house have to do with anything? As well, we know Esther didn’t have a father. She was orphaned as a child, and never knew him. So what does it mean that her father’s house will be destroyed?
A second oddity is with regards to the lineage of Mordechai. When we are first introduced to Mordechai, he is described as Mordechai, the son of Yair, the son of Shimi, the son of Kish. Now, the names Shimi and Kish appear elsewhere in Tanach. Shimi lived in the times of King David, and is famously known for cursing him. However, that Shimi wasn’t the son of Kish. He was Shimi, the son of Gera. Furthermore, the Kish in Tanach was known as being the father of King Shaul, not the father of Shimi. Due to this inconsistency, some infer that the ancestors of Mordechai named Shimi and Kish were unrelated to those from earlier in Tanach. That would mean then that Mordechai is not a descendant of King Shaul, for if he were, it would say that his father Yair was the son of Shaul, the son of Kish. However, our Sages understood differently. They say that Mordechai really was a descendant of King Shaul. If so, why doesn’t the verse say so?
One explanation for these oddities is that the Megillah story is really a repeat of history. As mentioned, King Shaul was commanded to eradicate the evil nation Amalek from this world. He hesitated, and the lone survivor, king Agag, managed to procure a descendant before he too was destroyed. Through that descendant, the nation of Amalek survived, eventually resulting in Haman. Since Shaul failed his mission, it was up to Mordechai, his own descendant, to complete the task. He had to stop Agag’s descendant, Haman. This was their final chance. As such, the Megillah sees Mordechai as stepping into Shaul’s place in history. It’s as if Mordechai himself is the son of Kish. Therefore, there was no need to mention Shaul in the ancestry of Mordechai. Mordechai was destined to fill his place.
Mordechai’s warning to Esther now makes sense. She too was a descendant of King Shaul. Mordechai knew that he didn’t have the ability to stop Haman. Only Esther did. She was a in a position of power, and her connection to king Achashverosh was the best way to put an end to Haman’s decree. The defeat and removal of Haman would rectify King Shaul’s failed mission. If Esther succeeds, then Shaul’s failure would cease to be. That’s only if she agrees. Mordechai was telling Esther that if she does not agree to make the effort to stop Haman, then everything would be in vain. She was put in this position exactly for this reason. If she doesn’t take advantage, then her father’s house, referring to King Shaul’s legacy, will be destroyed. He will forever remain a failure. It’s up to her.
The gemarra brings a contradiction. One verse implores the Jewish people to repent, as they have stumbled in their wanton sins. The term stumbling implies that it was considered a shogeg, meaning an unintentional sin, yet the verse calls it a wanton sin, which implies it was intentional. This teaches us that if someone repents, their intentional sins are regarded as unintentional sins. However, another verse says when a wicked person returns from their evil ways, and does justice and charity, by them he shall live. By them implies all of his acts, even the wicked ones, will cause the repentant to live. This teaches us that if someone who repents, their sins are even regarded as mitzvos! Which is it? The gemarra answers that if the repentance was out of fear, the sins are regarded as unintentional. However, if the repentance was out of love, the sins are transformed into merits.
There are commentaries that apply this teaching to the Megillah story. As stated, the Megillah story was essentially an opportunity to right past mistakes. King Shaul failed in his mission to destroy Amalek, and his descendants were tasked with rectifying these mistakes. Not only Esther and Mordechai, but that entire generation repented. Their repentance wasn’t out of fear. It was out of love! As such, these sins of King Shaul weren’t merely regarded as unintentional mistakes. Their repentance transformed these sins into tremendous mitzvos.
What was the miracle of the Purim story? Most would say the miraculous salvation of the Jewish people. There was a decree to exterminate every single Jew, man, woman, and child. The Jews gathered in prayer, Esther revealed her identity to Achashverosh, and they were granted a miraculous salvation. One could argue that this wasn’t so out of the ordinary. The Jews repented and prayed, and Hashem answered. What was so surprising? He is always willing to accept our prayer and repentance. Maybe the miracle was that everything turned upside down. Haman went from being the number two advisor in the kingdom to being executed. Mordechai went from wearing sackcloth to replacing Haman. This also isn’t so surprising, as Achashverosh clearly showed impulsive and inconsistent tendencies. What was it then?
The greatest miracle of the Purim story is from the very beginning of the Megillah. As mentioned, what was the root cause of Haman’s decree in the first place? The Jews, against the warnings of Mordechai, benefitted from Achashverosh’s party. What was so bad about this party? It was in celebration of the defeat of the Jewish people. It was filled with indecent behavior. Mordechai, the greatest sage at the time, told the Jews to stay away. They didn’t listen. What ended up happening at this party? Achashverosh got drunk, and that led to him executing his own wife. This paved way for Esther to become the Queen, and use her position to save the Jews. What does all this tell us? Hashem was already sewing the seeds of salvation, at the exact moment that the Jews were sinning. At that time, they didn’t deserve salvation. They hadn’t repented yet, as they were in the midst of sinning. Nevertheless, Hashem knew they would eventually repent. He was ensuring their eternal existence. This beyond imaginable Divine supervision is the greatest miracle of Purim.
If benefitting from Achashverosh’s party was so bad, to the point that Hashem’s intervention at that point was the greatest miracle of Purim, why are we commemorating it? Why is one of the mitzvos of Purim to have a celebratory party involving wine? Especially since drinking brings so many evils. The answer is because the Jews repented with love. That means that their sin of partaking of Achashverosh’s party is no longer a sin. Not only is it no longer regarded as a sin, it’s even regarded as a mitzvah. Such a terrible sin transformed into an incredible mitzvah. The joyous festivities on Purim are to demonstrate the tremendous merit we accrued from Achashverosh’s party. It’s to show how happy we are that the Jews at that time went to that party. This is also why Esther chose a drinking party as the means to bring about the downfall of Haman. She understood that the Jews going to Achashverosh’s party wouldn’t hinder her plan. She knew the Jews repented out of love, making their sin into a mitzvah.
We asked why it took so long in Jewish history for the Jews to willingly accept the Torah. Let’s answer this with a parable. There was a nice man who courted a woman from an exceedingly wealthy family. He and his family on the other hand had barely a penny to their name. The father of the bride told them not to worry, as the entire wedding celebration would be taken care of. They’ll pay for the band, the catering, the hall, the photography, the invitations, the centerpieces, even the sheitel. Their only condition is that the groom arrange his own suit. The family wasn’t sure how they would afford it, but after extreme difficulty they managed to buy him a discount suit that looked somewhat decent. It was the best they could do.
On the day of the wedding, on the way to the hall, the groom, dressed to his finest in the best he could afford, slipped and fell into a pile of mud. His suit was ruined. The family was devastated. They bumped into the father of the bride. He saw their situation and told them again not to worry. They tried their best, but at the end of the day the groom needs a new suit. His family will take care of it. They right away arranged for the groom to have an even nicer suit, and he looked magnificent at his wedding. He was so overjoyed. What’s the takeaway message?
At the end of a person’s life, they’re going to go up to the Heavenly court. They’ll have their bag full of their good deeds, but the court will notice this deficiency and that shortcoming. Like the groom in the story with the discount suit, sometimes our efforts can only go so far. In contrast, what happens when someone sinned, but their repentance was out of love? All of their transgressions are transformed into mitzvos. These mitzvos aren’t like the discount suit that the groom bought. After all, Who is the one granting the merit of these mitzvos? Hashem Himself. It’s like the wealthy father of the bride, who bought the best suit for the groom. This guy, who may have stumbled many times in his life, if he repents properly, ends up being on a higher level than someone who never sinned at all. The latter’s efforts are limited by human shortcomings. The former’s mitzvos were generated by Hashem.
The reason why the Jews didn’t merit to accept the Torah willingly at Mount Sinai was because they were too perfect. They hadn’t sinned yet, so their mitzvos were subject to human deficiency. However, once the Jews partook of Achashverosh’s party, they hit rock bottom. This atrocity generated the worst decree against the Jewish people in history. Their subsequent repentance out of love then gave them the greatest merit they ever had. Only then were they on the level capable of accepting the Torah willingly. Some even say that King Shaul knew this would happen. This was his whole intent in leaving Agag alive. This is how he could say “I upheld the word of Hashem”. Meaning, by leaving Agag alive, it led to the entire Purim story. It was this act which provided the merit to willingly accept the Torah. Because of him, Hashem’s word was truly upheld. Have a freilichen Purim and Good Shabbos!
 Based on a shiur by Rav Daniel Glatstein, given in 5780 (viewable at https://www.torahanytime.com/#/lectures?v=104627). He said it appears in his sefer on Purim, Maggid HaRakiah, although I don’t have access to it to confirm
 Megillah 7b; Shulchan Aruch Orach Chaim 695:2
 Eliyah Rabbah to Levush HaChur (Orach Chaim) 695:1, brought by the Be’ur Halacha ad. loc. § 2 s.v. חייב איניש
 See Megillah 15b
 Ma’amar Esther to Esther 6:14, by Rav Shlomo Kluger
 Megillah 12a
 Rabbi Glatstein goes so far as to say that the sin of eating at the meal of Achashverosh was the worst sin the Jewish people ever committed. Even though most would say that it was the sin of the Golden Calf, in that incident Hashem was willing to let Moshe live and the Jewish people continue through him (Exodus 32:10). This is in contrast to Haman’s decree, which was to wipe out every single Jew, even Mordechai and Esther, who did not take part in the sin
 The way Rav Shlomo Kluger asks it is אין קטיגור נעשה סניגור, a prosecutor cannot become a defense attorney (Rosh Hashanah 26a). This is why the Kohen Gadol doesn’t wear his golden garments on Yom Kippur, as it evokes the sin of the Golden Calf
 I Samuel Chapter 15
 Ibid v. 13
 Shabbos 88a
 Esther 4:14
 Ibid 2:7
 Ibid 2:5
 Ibn Ezra ad. loc.
 Megillah 12b
 See also Targum Sheni ad. loc., which gives the full lineage of Mordechai to King Shaul ben Kish
 Manos Halevi ad. loc. s.v. האמנה במה שדלג, by Rav Shlomo Alkabetz, the author of the Shabbos poem Lecha Dodi
 See Sefas Emes Purim 5637 on Esther loc. cit., who writes similarly. He then writes that he subsequently saw that Rav Shlomo Alkabetz preceded him with this idea. See also Esther Rabbah Pesikta § 7 and Alshich in his Mas’as Moshe ad. loc., which say that the entire Megillah story happened because of King Shaul’s failure. Listen to the shiur for more sources on this point
 Alshich loc. cit. 4:11
 Yoma 86b
 Hosea 14:2
 Ezekiel 33:19
 Shenei Luchos HaBris Torah Sh’B’Kesav parshas Tetzaveh § 30, explaining Esther Rabbah 9:4, and all those that will appear further down
 The Rokeach, in his Sha’arei Binah to Esther 4:7, brought by Manos HaLevi to Esther 4:5-8 s.v. ובשערי בינה, lists ten sins which King Shaul committed. This is why the Megillah sometimes spells יהודים with an extra י, which has the numerical value of ten
 See Derashos Chasam Sofer I p. 19 col. 1 s.v. הוא יפתח, who says that someone who ate a non-slaughtered animal and repented with love is considered as if they consumed the Pesach offering. See as well the Chida in his Kisei Dovid Derush LeShabbos Shuvah § 13 s.v. נמשך מזה and Devarim Achadim Derush LeShabbos HaGadol § 14 s.v. אך לטעם המפרשים who says this is the reason for במקום שבעלי תשובה עומדים אין צדיקים גמורים יכולים לעמוד (Berachos 34b), since the righteous are limited by 248 positive mitzvos, whereas the repentant can also turn their transgressions into mitzvos. The Dubna Maggid cited below says similarly
 Chasam Sofer in his Toras Moshe I, end of parshas Tetzaveh (LePurim), to Esther 1:1, and Derashos I p. 106 col. 1
 See Megillah 15b: אחשורש מלך הפהפך היה
 Megillah 11b, 12a
 See Sefas Emes Purim 5637 to Esther 4:16, who gives the same explanation
 Ma’amar Esther loc. cit.
 Dubna Maggid in his Kochav Ya’akov Haftaras VaEschanan to Isaiah 40:2
 The original parable had the suit getting stolen, but I suppose Rabbi Glatstein wanted to make the story more dramatic
 See Ecclesiastes 7:20
 This idea is brought in the name of Rav Yisroel of Ruzhin, the Ruzhiner Rebbe, in various places. Some examples are Chiddushei HaRim – Likkutei HaRim Haftaras Shabbos Zachor to I Samuel 15:13 and Yesodos Kodesh – Pardes HaTeshuvah Chapter 8 fn. 178