`246 A Primer on Amalek Part 6 From Agag to Haman
Chananya Weissman

December 13, 2022


Shaul's failure to wipe out Amalek when he had the chance is one of the great tragedies in history, for which we continue to suffer to this very day. Anyone with an ounce of knowledge and understanding yearns for the day when this mistake will be corrected; that will be true tikkun olam. Hopefully this series on Amalek will help educate the ignorant and wake up the slumbering, thereby bringing that day closer. We have to yearn for it.

The book of Shmuel tells us about the final moments of Agag, king of Amalek, progenitor of Haman. Shaul had taken pity on his fellow king, rivals though they were, and spared his life. The prophet Shmuel confronted Shaul the following morning and informed him that Hashem had rejected his kingdom for failing to carry out the mitzva. Shmuel then ordered Agag brought to him.

The navi writes that Agag walked to Shmuel “מעדנת” (Shmuel I 15:32). The commentaries offer different interpretations of what this means. Some say it means Agag was in chains (Metzudas David, Ralbag, Radak's second interpretation, Abarbanel). Others say it means he walked daintily, with joy and confidence befitting a king (Radak's first interpretation, Malbim).

The navi then records Agag's dramatic last words: “אכן סר מר המות”. Once again, the commentaries differ over how these words are translated. Rashi, Radak, and Metzudas David explain them as “Indeed, the bitterness of death has arrived upon me.” It is unclear according to this explanation why it was important for Agag's final words, unlike those of so many others, to be preserved and written in our holy books.

Others translate his words as “Indeed, the bitterness of death has been removed.” According to Ralbag, Agag thought that a pious and merciful person like Shmuel would take pity on him and let him live. Of course, sparing Amalek when you have him in your clutches is the very opposite of piety and a distortion of mercy. As Abarbanel writes: “Shmuel commanded them to bring Agag, king of Amalek, to him, for as an elder, a pious man, and a prophet, he wanted to sanctify God's name with his own hand, that his own sword should consume [Agag's] flesh.”

Abarbanel and Malbim follow this translation of Agag's final words, and explain that the bitterness of death had been removed because, as an exalted person, Agag preferred death to a life of captivity and shame. According to a similar explanation by the Chida, in his commentary Chomas Anach, Agag feared that he would be put to death by an ordinary person, which would be shameful to a king. When he saw that someone of Shmuel's stature would be the executioner, the bitterness of his impending death was removed.

While Agag may well have desired a more honorable death, one still wonders why these final words were significant enough to be recorded with divine inspiration.

This question is best answered by a deeper explanation of his words, which comes from an ancient tradition that is also cited by the Chida. During Agag's final night, when he was in captivity, he impregnated a woman. According to some versions it was a maid, but the Chida writes that it was his wife. The Chida adds that Agag “performed sorcery to save her”. (We saw last time how Haman accused Moshe and the Jewish people of engaging in sorcery; they always accuse us of what they are doing.) This fateful tryst perpetuated the nation of Amalek, including Haman.

This is what removed the bitterness of death from Agag. He knew that Amalek's age-old war against Hashem, His people, and His world would continue after him. With that knowledge alone he could die with a smile on his face.

According to this we can well understand the significance of his last words. The navi is illustrating what we learned previously from the Torah, that Amalek's war against Hashem is from generation to generation (Shemos 17:16). It is the essence of their existence, and they are always planning their next attack. It behooves us to be vigilant and never lose sight of this.

As we have also learned, Amalek fights this war through artifice and deception. They disguise themselves as other nations when they attack us, they assimilate into other nations to subvert them, and they prey on those who waver spiritually to lead them into the abyss.

In the previous part we learned about Haman's letter to the nations of the world in which he “koshered” a holocaust. The Midrash (Esther Rabba 7:13) relates that Haman didn't merely orchestrate the physical war against the Jewish people, but he first went to great lengths to wage spiritual war against them, in order to make them vulnerable.

Rabbi Yitzchak Nafcha said, Haman the wicked came with great artifice against Israel...Haman said to Achashverosh, “The God of these people hates licentiousness. Set up prostitutes for them.” He then made a party and decreed upon them that they should all come, and eat and drink and do according to their will, as it says (Esther 1:8) “To do according to the will of each man.”

When Mordechai saw this, he got up and announced to them [the Jews] and said to them, “Do not partake of the meal of Achashverosh, for he only invited you to bring prosecution upon you, in order that there will be an opening for the [divine] attribute of justice to prosecute against you before the Holy One, blessed is He.”

But they did not listen to Mordechai, and they all went to the party house.

What a revelation this is! We are usually taught that Achashverosh made the party merely to show off his lavish wealth, engage in unbridled hedonism, and, on a deeper level, celebrate what he thought was the expiration of the prophecy that the Jews would be redeemed. As degenerate as this is, such behavior would be relatively benign for a Persian emperor. Let him act like a boor as long as he left the Jews alone.

But there was much more going on behind the scenes. The entire party was a diabolical plot hatched by Haman to ensnare the Jews in sinful behavior, which would cause them to lose divine protection. Haman would then implement the final solution.

We cannot even fathom the wealth that Achashverosh spent on this party, which spanned more than half a year, all for the sake of tempting the Jews to sin. Naturally, the Jews were invited as honored guests, as free people, as equals, with kosher food prepared to their strict specifications. The spiritual poison always comes with hype and premature festivities, as enlightenment, new morality, technological marvels, and miraculous injections that will save the world.

For it to be effective, for it to bring spiritual prosecution upon the Jewish people, they have to agree to take it. Then the swords can be sharpened.

But they did not listen to Mordechai, and they all went to the party house.

The Jews believed Mordechai was a “conspiracy theorist”, a party pooper, a religious extremist who threatened the good relations they had cultivated with the government. Not only that, but Mordechai was urging them to defy a royal edict to partake of the festivities. Surely there were many rabbis at the time who argued that there were grounds for leniency, even that it was a mitzva to go to the party. Mordechai, with his outdated rigidity and senseless talk about Amalek, was endangering everyone!

Of course, it was Mordechai's unwavering faithfulness, like Moshe's raised hands, that defeated Haman and saved the Jews from annihilation.


Most people don't know this – a million dollars in yeshiva tuition doesn't buy much actual knowledge these days – but while all this was happening in Persia, the Jewish return to Israel from the Babylonian exile was already in full swing.

Unfortunately, the vast majority of Jews – especially the young – had grown fond of life in exile. They forgot the curse it is to live outside of the Land of Israel, even under favorable conditions, and the desecration of Hashem's name that the diaspora represents, irrespective of the spiritual situation within Israel. They declined the call to return home when the window of opportunity was open, which sabotaged the potential redemption from the very beginning. (For much more on this, see Go Up Like a Wall.)

It is no wonder that galus Jews were susceptible to Haman's plot and eagerly attended Achashverosh's party. It is also no wonder that they received a serious wake-up call and faced total destruction. This story has repeated itself to the present day like a bad movie on a loop.

Life in Israel was materially difficult and fraught with danger, as the foreign occupiers of our land were not pleased to see the Jews return. With great determination and self-sacrifice, under constant threat from their enemies, the Jews rebuilt the foundation of the Beis Hamikdash.

It was then that their enemies tried a new tactic. “Let us build with you,” they said to the leaders of Israel. “We want to serve your God just like you.” (Ezra 4:2)

It is the nature of the galus Jew to ingratiate himself to the gentile, to crave his approval, to grovel for his assistance and partnership, but these Jews knew better. They politely but firmly refused this offer of “help”, which was really just a ploy to sabotage the rebuilding of the Beis Hamikdash from within.

The foreign occupiers then hired advisers to help them foil the Jews (4:5).

Their next move, presumably at the behest of this professional advice, was to slander the Jews. They sent a letter to the Persian king, in which they claimed that Jerusalem historically only brought destruction upon the world. They warned him that the Jews were rebuilding the city and the Beis Hamikdash in order to rebel against Persian rule, and asked for permission to destroy whatever the Jews had rebuilt so far (4:6-16).

This might be the earliest record of these anti-Jewish tropes, right there in Tanach.

The scribe who wrote the letter was a man by the name of Shimshai (4:8).

Shimshai was the son of Haman.

While Haman was actively conspiring to annihilate the Jews in the diaspora, his son was conspiring with foreign occupiers and Jewish traitors to destroy the Jews in Israel.

There is nothing new under the sun. Amalek is always there behind the scenes.

In the next and final part, we will see an astounding example of this that will bring us full circle.


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