The Torah in the Book of Debarim, in the final verses of Parashat Ki-Teseh, establishes the command of "Maho Timhe Et Zecher Amalek" – to eradicate the memory of the wicked nation of Amalek.
Interestingly, this obligation assumed practical Halachic significance following World War II, when Germany agreed to pay reparations to Jews. The Gaon of Vilna (1720-1797) taught that the Germans descend from Amalek. In fact, when the German Emperor Wilhelm II visited Jerusalem in 1898, Rav Yosef Chaim Sonenfeld (1848-1932) felt that the Jews should not go to see him, even though generally there is value in seeing kings, because of the Gaon of Vilna’s tradition, that the Germans descend from Amalek. Accordingly, after the Holocaust, the question arose whether the command to eradicate Amalek includes a prohibition against benefiting from Amalek’s property, such that it would be forbidden to accept money from Germany.
Rabbenu Bahyah (1255-1340), in his Torah commentary (Parashat Beshalah), writes explicitly that it is forbidden to derive any benefit from the property of Amalek. He explains on this basis why the Megila emphasizes that after the Jews waged war against their enemies in Persia, "U’ba’biza Lo Shalehu Et Yadam" – they did not take any spoils. Since this war was waged against Haman and his followers, who belonged to Amalek, they were not permitted to benefit from the possessions. Likewise, Rabbenu Bahya writes, King Shaul was punished because, after waging war against Amalek, he took Amalek’s cattle as spoils of war, and this property was forbidden for use.
As many have noted, however, other sources appear, at first glance, to contradict this conclusion. For one thing, the Rambam (Rav Moshe Maimonides, Spain-Egypt, 1135-1204), in presenting the Halachot relevant to the command to eradicate Amalek, makes no mention of such a prohibition. What’s more, we read in the Book of Shemuel I that David, before he became king, waged war against an Amalekite tribe and seized their animals for use by him and his men. And, we read in Megilat Ester that after Haman’s execution, Ester gave "Bet Haman" ("Haman’s home") to Mordechai. The Gemara in Masechet Megilla (10) shows from this verse that Providence arranges that the wicked become wealthy so that their fortunes will later be given to the righteous. It is clear that the Gemara understood that Mordechai received Haman’s assets. Haman, of course, is a descendant of Amalek, and yet Mordechai received his fortune – seemingly proving that it is permissible to benefit from the property of Amalek.
The Meshech Hochma (Rav Meir Simcha of Dvinsk, Lithuania, 1843-1926) suggests answering this question by distinguishing between individuals, and the Jewish Nation as a whole. The prohibition discussed by Rabbenu Bahya forbids the Jewish Nation to collectively benefit from the possessions of Amalek. Therefore, when King Shaul waged war against Amalek, and when the Jews waged war against their enemies in Persia, it was forbidden to seize the spoils. However, David waged war against an Amalekite tribe before he was king, as an individual, and Mordechai similarly was given Haman’s wealth as an individual, and therefore, this was allowed.
A different answer is given by the Oneg Yom Tob (Rav Yom Tob Lipman Halperin, 1816-1879), in the introduction to his work. He writes that the obligation to eradicate the memory of Amalek includes a prohibition against taking its possessions, because if one has Amalek’s possessions, the memory of Amalek is retained. Therefore, when King Shaul was commanded to wage a war of annihilation against Amalek, he was not to have taken any of Amalek’s possessions. However, once the nation of Amalek in any event has yet to be eradicated, its possessions may be received and used. Therefore, in the times of David and Mordechai, it was permissible to take the possessions of Amalek, because Amalek in any event was not eradicated. Strictly speaking, the Jews were permitted to seize the possessions of their enemies in Persia, however, as Mordechai was a descendant of King Shaul, he had the Jews leave the spoils in order to rectify the mistake made by his ancestor, who took Amalek’s cattle.
The Poskim note that according to both these approaches, it would be permissible for Jews affected by the Holocaust to receive reparations from Germany. These reparations were received as individuals, not by the Jewish Nation as a whole, and so according to the Meshech Hochma, this is allowed. And, according to the Oneg Yom Tob, this would certainly be permissible, because if we indeed assume that Germany descends from Amalek, then Amalek is not eradicated in any event, and so its possessions are permissible.
Another basis for accepting reparations was proposed by Rav Yosef Dov Soloveitchik of Boston (1903-1993). Citing his grandfather, Rav Chaim Soloveitchik of Brisk (1853-1918), Rav Soloveitchik advanced the theory that the obligation to eradicate the nation of Amalek applies not only to the nation of Amalek itself, but also to any nation who follows Amalek’s example of hostility to the Jewish People. He proved this theory from the Rambam, who, in Hilchot Melachim, discusses the command to eradicate the seven Canaanite nations, and concludes, "U’kbar Avad Zichram" – we no longer can identify the descendants of these nations. In the next passage, however, where the Rambam discusses the obligation to eradicate the nation of Amalek, he does not end with this conclusion. This might suggest that in contrast to the Misva to eradicate the seven Canaanite peoples, which applies only with regard to those actual nations, the Misva to eradicate Amalek is not limited to Amalek. Rather, it was said regarding all nations that follow Amalek’s example of hostility, even today. Rav Soloveitchik also cited the comment in the Talmud Yerushalmi (Yebamot 2:6) that although the Megilla identifies Haman as "Haman the son of Hamedata," Haman was not actually the son of Hamdata. Rather, this verse means that Haman was a murderous villain just like his father was. It turns out, then, that Haman may not have even been a biological descendant, and yet the war against Haman is considered a war against Amalek – showing that the status of "Amalek" is not limited to actual descendants of this nation.
As such, Rav Soloveitchik asserted, even if the Germans are not the biological descendants of Amalek, they would be included in the Misva to eradicate the memory of Amalek.
However, Rav Soloveitchik stated, there still is a difference between biological Amalekites and others who are considered like Amalek by virtue of their hostility to the Jewish Nation. When it comes to the obligation to wage war against the nation of Amalek, this obligation applies to all nations who resemble Amalek. But with regard to the law of "Maho Timhe," to eradicate the nation of Amalek, which includes, as we have seen, a prohibition against benefiting from Amalek’s property, this prohibition is limited to biological Amalekites. According to this distinction, too, it would be permissible to receive reparations from Germany.
Nevertheless, there were those who opposed accepting reparations not on halachic grounds, but rather in order not to allow the Germans the opportunity to ease their conscience. Many felt that accepting reparations enabled the Germans to feel absolved of their guilt for the unspeakable crimes they committed against the Jews, as though they could make amends by paying money. A precedent to this argument is the verse in the Book of Shemot in which G-d commands Moshe before the Exodus from Egypt, "Please speak in the ears of the nation" that they should ask the Egyptians for their riches before leaving the country. The Gemara in Masechet Berachot comments that Moshe had to "beg" the people to bring the Egyptians’ wealth with them ("Please speak…"), because G-d had made a promise to Abraham Abinu that his descendants would emerge from their period of bondage with great wealth. Apparently, if not for G-d’s promise to Abraham, the people would not have wanted to bring the Egyptians’ riches with them. Some have explained that the people did not want the Egyptians to feel they could clear their conscience for their inhumane treatment of Beneh Yisrael by giving them money. Beneh Yisrael’s instinct was to refuse the Egyptians’ money so that the Egyptians would not feel that they had atoned for their persecution. By the same token, many felt it would be inappropriate to accept reparations from the Germans because it would convey the mistaken message that Germany thereby earns expiation for what it did to European Jewry.
In conclusion, it is worth noting a very meaningful insight by Rav Avigdor Nebenzahl (contemporary) regarding the Torah’s outlook on Amalek. Rav Nebenzahl observed that although the Torah requires eradicating the nation of Amalek, nevertheless, the Rambam rules that an Amalekite may convert and join the Jewish People. Proof to this view may be brought from the Gemara’s remark in Masechet Gittin (57) that Haman – an Amalekite – had descendants who taught Torah Bnei-Brak. This would certainly indicate that members of the nation of Amalek can convert and become full-fledged Jews, which is how Haman ended up having descendants who taught Torah. And, it seems from the Rambam that a convert from Amalek may even marry a Jewish woman. This is in contrast to the nations of Amon and Moab, whom the Torah forbids allowing to marry a Jew after conversion. The Torah explains that these nations are forever barred from the Jewish People because they did not offer provisions of food and water to Beneh Yisrael after the Exodus. Amon and Moab descend from Lot, Abraham Abinu’s nephew, who was rescued from the destruction of the city of Sedom solely in the merit of Abraham Abinu. These nations thus owed an enormous debt of gratitude to Beneh Yisrael, yet they refused to offer assistance – or even sell provisions – when Beneh Yisrael were traveling in the desert after leaving Egypt. The Torah therefore forbids allowing them to join our nation.
Interestingly, Rab Nebenzahl noted, Amalek, who waged an ideological battle against Am Yisrael, may convert and join our nation, but Amon and Moab, who showed ingratitude, cannot. Rav Nebenzahl explained that if somebody has the wrong beliefs and ideas, he can be taught and educated. However, if somebody is plagued by negative character traits, it is exceedingly difficult for such a person to change. Indeed, Rav Yisrael Salanter (1810-1883) taught that changing even one character trait is more difficult than studying the entire Talmud. Therefore, Rav Nebenzahl explained, a person from Amalek, a nation that opposed us ideologically, can join our nation, because he can be taught the correct beliefs and given proper knowledge. A person from Amon and Moab, however, can never join our nation, because these nations are afflicted with negative character traits – specifically, ingratitude – an this is exceptionally difficult to change. Hence, such a person can have a profoundly negative effect upon our nation if he would be allowed to join us.
An earlier source of this general concept is a discussion of the Ran (Rabbenu Nissim of Gerona, Spain, 1320-1380), in one of his Derashot (11), regarding Abraham Abinu’s insistence that his son, Yishak, not marry a woman from Canaan. Abraham sent his servant to his homeland, Aram Naharayim, to find a girl for Yishak, rather than find a suitable match from the local population in the land of Canaan. The reason, the Ran explained, is because although the people in Aram Naharayim worshipped idols, their characters were not as flawed as those of the people in Canaan. Abraham understood that incorrect beliefs can be overcome through proper education, but negative character traits often remain permanently embedded within a person’s nature. As he was forming the foundation of Am Yisrael, Abraham knew that somebody from Canaan cannot play any role in this process, because such a person could inject negative Middot (character traits) into the fabric of the nation, thus having disastrous long-term consequences. He therefore insisted on finding a mate for Yishak from Aram Naharayim.
Summary: When the Germans offered the Jews reparations after World War II, there was considerable controversy surrounding the question of whether this money should be accepted. From a strict Halachic perspective, it seems that accepting the money is allowed. Nevertheless, some felt that this would be inappropriate, as it would give the impression that Germany could simply buy expiation for the unspeakable crimes perpetrated against European Jewry.