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1) CONVERTS FROM THE DESCENDANTS OF AMALEK
QUESTION: The Gemara teaches that grandsons of Haman learned Torah in Bnei Brak. This seems to contradict the Mechilta (Beshalach 2:16) which comments on the verse, "... for the Hand is on the throne of Hash-m, there is a war for Hash-m against Amalek throughout all generations" (Shemos 17:16). The Mechilta says that this verse teaches that Hash-m made an oath on His Throne of Glory that if a member of any of the nations will come and ask to convert, he may be accepted, but no member of Amalek and his offspring may be accepted as a convert.
The IYUN YAKOV in Sanhedrin (96a, DH Mipnei) asks that since Haman was a descendant of Agag the Amalekite (see Esther 3:1), how is it possible that his grandsons converted and learned Torah?
ANSWERS:
(a) The CHAZON ISH (YD 157:5) suggests that the lineage of the grandsons of Haman became mixed with the lineage of other nations, and thus Beis Din did not realize that they were descendants of Amalek and accepted them as converts. When converts from Amalek have already been accepted, b'Di'eved they are valid converts.
(b) Alternatively, the Chazon Ish answers that the RAMBAM (Hilchos Melachim 6:4, with the comment of the RA'AVAD) maintains that Beis Din indeed may accept Amalek converts when they come to be converted. The Mechilta, which states that no converts may be accepted from Amalek, refers to when the Amalekites wage war with the Jewish people and then decide to make peace and to convert. In this situation, converts from other nations are accepted but not converts from Amalek (see TOSFOS to Sotah 35b, end of DH l'Rabos).
The Chazon Ish cites support for this distinction from the Gemara in Avodah Zarah (10b) which relates that the righteous Roman, Antoninus, asked Rebbi if he would receive a portion in Olam ha'Ba. Rebbi replied that he would. Antoninus asked him, "But does the verse no say that 'there will be no remnant for the House of Esav'?" (Ovadyah 1:18). Rebbi replied that this verse refers only to those who perpetuate the evil ways of Esav. If, however, the Nochri abandons these ways, he can merit a share in Olam Ha'Ba. Similarly, a descendant of Amalek who did not personally enter any war against the Jewish people is not considered as "going in the way of Amalek," and he may be accepted as a convert.
(c) RAV SHALOM SHWADRON zt'l (in his notes to LEV ELIYAHU, Bereishis, p. 71) explains that the Rambam must have understood that the Gemara argues with the Mechilta. This is implied by the fact that the Rambam (Hilchos Isurei Bi'ah 12:17) states that Beis Din may accept a convert from any nation other than Amon, Moav, Mitzrayim, and Edom.
The Lev Eliyahu explains the reason for why an Amalekite is accepted as a convert, while an Amonite or Moabite is never accepted as a convert (Devarim 23:3). The Torah (ibid. 23:5) states that a member of the nations of Amon and Moav may not be accepted as a convert because those nations did not greet the Jewish people with bread and water when they traveled through the desert after they left Mitzrayim. Their failure to provide bread and water demonstrated their degenerate Midos (character traits). The verse in Bereishis (19:29) states that Hash-m saved Lot from the destruction of Sedom and Amora through the merit of his uncle, Avraham Avinu. Amon and Moav, who were descendants of Lot (see Bereishis 19:37-8), should have recognized the good deeds done to them by the forebear of the Jewish people. When they not only failed to help the Jewish people in the desert but actively were hostile to them (see Devarim 23:5, that they hired Bil'am to curse the Jewish people), they demonstrated their degenerate Midos and forfeited their right to be part of the Jewish people.
A member of Amalek, on the other hand, may not become part of the Jewish people for a different reason, because "he did not fear Hash-m" (Devarim 25:18). When Amalek clings to his position of war against Hash-m, they are the Jewish people's worst enemies. However, since their sin is on the intellectual level and not so deeply entrenched in their Midos, if a descendant of Amalek abandons the way of his fathers and recognizes their perverse ways, he indeed may repent. Therefore, if a descendant of Amalek sincerely repents and seeks to follow Hash-m's Torah, he may be accepted as a convert. (D. Bloom)