According to the Halacha (Shulchan Aruch Orach Chaim 694:1), each Jew is required to send two matanos la’evyonim, charitable gifts, to at least two poverty-stricken Jews on Purim.
The Rambam (Mishneh Torah, Hilchos Megillah 2:17) points out that the more poor people one sends to, the better. In fact, he writes (ibid. 2:16) that it is better to spend more money on the gifts to the poor than on any other mitzva of Purim.
This idea is echoed in the Mishna Berura (694:3). Furthermore, as opposed to standard charitable contributions, we are to give liberally and with no investigations as to the veracity of the poor person’s claim needed.
The Chasam Sofer explains that the reason that we even give to the undeserving is because we were not entirely deserving of being saved in the Purim story.
The Klausenberger Rebbe explains that another reason for not needing to investigate is that we should not worry about where the money is going because H-Shem reversed the situation described by the Midrash (Esther Rabba 7:25) that the gentiles teasing the Jews that they would kill them and said, “we’ll take your money.” Since this fear was reversed, on Purim we should not worry where our wealth is going.
R’ Shmuel de Ozeida notes that there is a missing letter vuv in evyonim (“poverty-stricken”) to hint to this same idea that we do not need to investigate if the person is completely poor enough to be Halachically considered an evyon.
The Dena Pishra explains the inordinate focus on the poor on Purim as indicative of the fact that everyone was saved on Purim – rich and poor.
The Ben Ish Chai quotes the Midrash (Esther Rabba 7:23) that Haman mocked Pharaoh that he only killed the males (Shemos 1:16). Therefore, writes the Bein Ish Chai, the Halacha requires us to give matanos la’evyonim to two people because Haman, on the contrary, wanted to kill males and females.
The Peleh Yo’Eitz explains that this gift is meant to help the poor celebrate Purim, and not even worry about the upcoming costs of Pesach. Also, it would help strengthen the emunah of the poor, who regularly rely on the rich, and the rich rely on H-Shem.
The is similar to the anecdote when Mayer Anschel Rothchild was asked how he could shovel so much money to charity, and he famously quipped, “ G-d has a bigger shovel.”
The Gerrer Rebbe quotes the Talmud (Megillah 7b) that we are supposed to skip Torah learning and even prayer for the public reading of Megillas Esther on Purim, however chesed cannot be pushed aside. Of the three legs on which the world stands according to the Mishna (Avos 1:2), chesed cannot be removed for the world to remain.
The Alshich writes that one should mentally intend to give matanos la’evyonim in the merit of Moshe.
Rav Dan Segal notes that the mere idea that Moshe Rabbeinu requires our efforts in his honor demonstrates that we have so little idea of the heavenly impact of our actions.
To demonstrate a similar powerful idea, the Ben Ish Chai points out that the gematria of matanos (“gifts”) (40+400+50+6+400=896) is the same as manos (“gifts”) (40+50+6+400=496) and 400.
The number 400 in the Zohar (I:123b) represents evil influences. The verse uses this particular word for gifts to emphasize that giving matanos la’evyonim can provide us with the spiritual power to fight off unholy forces.
According to the Halacha (Shulchan Aruch Orach Chaim 695:4), each Jew is required to send two foods to at least one other Jew on Purim.
The Peleh Yo’Eitz notes that the best way to perform the mitzva is for a great person to give to a lesser member of society. This would create both joy and the potential for one mitzva to lead to others.
After all, as the Sfas Emes emphasizes, one of the intents behind this mitzva is to debunk Haman’s slander (Esther 3:8) that Jews are splintered. Besides, acts of chesed are the foundational groundwork for the rebuilding of the Beis HaMikdash (bimheira biyameinu).
Perhaps this is one reason for the Talmudic opinion (Megillah 7b) that one could also fulfill one’s obligation of mishloach manos by sending Torah.
Interestingly, Rav Shlomo Alkabetz wrote the oft-quoted M’nos HaLevi as a mishloach manos gift to his in-laws.
In Eparyon, Rav Ganzfried, author of the Kitzur Shulchan Aruch, considers mishloach manos as a cunning way to give charity. Since all people will be giving gifts to their friends, the poor would not feel embarrassed by accepting a handout. This also explains why the order of the mitzvos listed in this verse seems out of order, with the more important mitzva of tzedaka being mentioned last.
The Sha’arey Simcha writes that the reason for this order is that it is debatable which miracle was greater: the destruction of our enemies or the raising of the Jews. Therefore, there are two mitzvos, paralleling each of these miracles, respectively.
The Ohel Moshe notes that, as opposed to other Holy Days, where the mitzvos of the day (i.e. lulav, matza, shofar, etc.) are only relevant for those days, Purim’s mitzvos (i.e. tzedakah, chesed, learning Megillas Esther, etc.) are relevant all year long.
R’ Meir Yechiel of Ostrovtza says that the implication of the word “re’eyhu” (“his fellow”) is that every Jews is considered worthy of receiving mishloach manos on Purim in H-Shem’s Eyes.
The Chasam Sofer was asked if mishloach manos are Halachically for increasing unity or to help all Jews have the minimal means with which to celebrate. If it is for unity, then it is for the benefit of the giver; if it is to allow everyone to celebrate, it is for the receiver. A practical difference would be in a case where someone refuses to accept. In such a case, has the sender fulfilled one’s obligation? If it is for the giver, the answer is yes, whereas if it is for the receiver, the answer is no.
Once, when about to receive mishloach manos, the Brisker Rav looked outside to check if it was yet sunset, and thus no longer Purim. He was willing to accept mishloach manos for purposes of the mitzva, but was unwilling to accept it as a regular gift, in fulfillment of the words of the wisest of men (Mishlei 15:27) that one “who hates gifts lives.”
Regarding the unique language of this verse, the Ben Ish Chai notes that the gematria of manos (“gifts”) (40+50+6+400=496) is the same as the 50 cubits of Haman’s gallows with the word maves (“death”) (40+6+400=446), meaning that this mitzva is intended to remind us of Haman’s plan to kill Mordechai.
According to the Ben Ish Chai, the verse emphasizes that Haman prepared the gallows on which he dies because if the wood of the gallows was made from the beams of the Beis HaMikdash, and the Halacha as brought down by the Rambam (Mishneh Torah, Hilchos Shegagos 9:1) would not allow Mordechai to make use of it. However, since the wood of this beam has already been used by Haman, this removed its sanctity, making it usable to kill him.
According to the Ora V’Simcha the gematria of ha’eitz (“the tree”) (5+70+90=165) is the same as Haman (5+40+50=95) + 70. Seventy are the number of days Haman was in power. According to the Chida, seventy is also the number of verses between Haman’s rise to power (Esther 3:1) until his downfall (Esther 7:10). Finally, seventy is also the gematria of yayin (“wine”) (10+10+50=70). The very wine with which Haman intended to seduce the Jews of Persia to sap them of their spiritual power is what led to his undoing. This may be yet another reason for the Talmudic custom (Megillah 7b) to drink an unusually large amount of wine on Purim.
R’ Yechezkiel Levenstein writes that many people recognize that their suffering comes from their own sins, but they do not realize that the sin, itself, creates the punishment.
Megillas Sesarim says Esther was arguing here that her not being summoned in the last thirty days was indicative of the fact that she soon would have to be requested.
R’ Yaakov of Dubno gives the opposite answer – since Achashverosh had not called her in thirty days, Esther feared that he had lost interest in her.
Kisei Shlomo writes that Esther realized that the Jews’ salvation would really not come from her, but through their own teshuvah. She therefore picked the large number of days to buy time for the Jews to repent on their own.
The Maharal quotes from the Talmud (Brachos 58b) that a person who is reunited with a friend after thirty days says the blessing of Shechechiyanu. The Maharal explains that the reason for this is the intense joy brought about by the cessation of the absence. In other words, Esther emphasized that she had not been summoned for thirty days to clarify that when Achashverosh will actually summon her after so long a separation, his emotional state will be far more amenable to her suggestions.
According to Rav Yitzchak Hutner, this entire conversation justifies the custom of drinking on Purim ad d’lo yada, up to the point that one does not know the distinction between “blessed is Mordechai” and “cursed in Haman” (Talmud, Megillah 7b). He explains that, during the rest of the year, we are warned against digging deep into the secrets of the world, like the material from which the Earth was made, the symbolic meaning of Yechezkiel’s vision of H-Shem’s chariot and retinue, etc. On Purim, however, the point of drinking is to break down our inhibitions, open our minds, and reach levels of intellectual understanding to which we are not usually privy. On Purim, too, we are able to enter the courtyard of the King, and He will allow us to comprehend that which we were otherwise not invited to understand.