Why Amalek Came Out to War Against Israel

"Then Amalek came." It is written, "Grant not, O LORD, the desires of the wicked" (Psalms 140:9). Come and see the difference between the strength of those who came out of Egypt and the seed of Esau. Those who came out of Egypt gathered and dwelt with one commandment in their hand: they would circumcise their sons in Egypt. The Egyptians said to them, "Why do you circumcise them? Let them be like the sons of Egypt, and the hard labor will be eased from you." Israel answered them, "Did Abraham, Isaac, and Jacob forget their God in heaven, that their children after them should forget Him?" The Egyptians said, "Why do you circumcise them, when after a while we cast them into the Nile?" Israel answered, "We will circumcise them, and afterward do as you wish." But the seed of Esau was not so. As long as Isaac was alive they upheld circumcision among themselves, but once he died they abolished it. They told a parable. To what is the matter compared? To a king who gave his crown to his beloved friend and said, "Let this rest upon your head and upon the head of your sons forever." The friend kept it on his head until he entered his eternal home. Afterward the king said, "I will go and see whether my friend's son keeps his father's writ upon his head." He went and found it thrown into the rubbish heap, and he turned back in great wrath, as it is said, "O LORD, when You went forth from Seir... the mountains flowed down before the LORD" (Judges 5:4-5 / Deuteronomy 33:2). To what are the wicked Esau, Eliphaz, his son Amalek, Jeroboam son of Nebat, Haman the Agagite, and Nebuchadnezzar likened? To one who found a garment on the road, seized it, brought it into the city, and proclaimed, "Whose lost item is this?" All the townsfolk gathered and came out to meet him, saying, "See how righteous, how pious that man is!" At once they stood and made him head and officer over them for a year, two, three, until he destroyed the whole city. So are the wicked likened. For the two tears Esau shed before his father, they gave him Mount Seir, from which the rains of blessing never cease. For Jeroboam, who answered a word before the King, they gave him ten tribes. For Merodach, who showed honor to our Father in heaven, Nebuchadnezzar came forth from him. For Agag, who wept and pleaded while imprisoned, saying, "Woe is me, perhaps my seed is lost from the world," Haman came forth from him. Eliphaz the Temanite spoke to his son Amalek when Amalek asked, "Father, who will inherit this world and the world to come?" He told him, "The children of Israel inherit this world and the world to come; go out and dig wells for them and prepare their roads, and if you do so your portion will be with the lowliest among them and you will enter the world to come." But he did not do so; instead he went out to destroy the whole world, as it is said, "Then Amalek came and fought." The Holy One, blessed be He, said to him, "Wicked one, I formed you after seventy tongues, and now you shall be My foremost in punishment for all who descend to Gehinnom," as it is said, "Amalek was the first of the nations" (Numbers 24:20), and it says, "For I will utterly blot out" (Exodus 17:14).