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.
The Talmud (Megillah 7a) notes that one of the proofs that Megillas Esther was written with ruach hakodesh (see Introduction) is that no human writer could possibly know that the Jews did not take any spoils.
Rashi writes that the Jews had rights to the spoils, but decided to wave those rights, and give the spoils to the king in order to maintain friendly relations with the palace.
The Dena Pishra writes that they did not take spoils because they did not want others to think that the Jews’ motivation was financial.
In M’aarchei Lev, Rav Moshe Schwab writes that since this was the property of Amalek, it was forbidden to take, as was the case for Shaul (Shmuel 1 15:3). and this is why the Jews refrained from doing so here.
In fact, the Binyan Ariel and Nachal Eshkol write that the Jews’ self-control in this incident was a tikun for the sin of Shaul in sparing (Shmuel 1 15:9) Amalek’s property.
Interestingly, the M’lo HaOmer and Me’am Loez both note that the initial letters of the ninth, tenth, eleventh and twelfth words of this verse, uvabeeza lo shalchu es (“and from their spoils they did not send”) can be rearranged to spell Shaul.
The Sfas Emes writes that the Jews took the spoils, but destroyed them in an effort to not benefit from the property.
However, R’ Yitzchak Yeruchem Diskin writes in Ohelim that Jews have an obligation to take the property of Amalek and destroy it, but did not do so here. The reason was that the Talmud (Megillah 16a) considers Haman to have been a slave. As such, he relinquished all rights to personal belongings. This includes his children. This also answers the question of how his grandchildren could study Torah in Bnei Brak if Amalek is never allowed to join the Jewish people. Such is not the case for his grandchildren because of his status of being a slave.
Megillas Seris adds another reason they did not take the spoils – they only had one day to kill Amalek, and they did not want to run the risk of missing the opportunity to fulfill this mitzva. In the course of performing a mitzva, they totally ignored anything ancillary to killing out their enemies.
The Gerrer Rebbe notes that matanos la’evyonim, the Halachic (Shulchan Aruch Orach Chaim 695:4) injunction to donate to the poor on Purim is in honor of the impoverished Jews of the time not taking the spoils of their enemies, despite their needs.