Why was Amalek punished more severely than all the other nations who did evil to Yisrael?
(25,17) “Remember what Amalek did to you on the way when you went out of Egypt. How he happened upon you on the way and cut off all of those who were weakened in the rear, and you were exhausted and weary and he did not fear G-d.”
Since the Torah could have been much more brief, saying simply “Remember what Amalek did to you, how he cut off all those who were weakened in the rear”, why did the Torah go into so much detail here?
We can answer this question once we understand why Amalek was punished much more severely than all the other nations who did evil to Yisrael. For example, although Egypt enslaved Yisrael under harsh conditions for 210 years, and according to the teachings of Chazal they buried many babies in the construction of their buildings and slaughtered three hundred babies every day, even so Hashem did not decree that they must be erased from the world.
Similarly Babylon, Media and Greece who did much evil to Yisrael with their evil decrees, killings and afflictions, were nevertheless not punished by being wiped out from the world. So why was Amalek who did comparatively little evil to Yisrael, killing only some of the men from the tribe of Dan who traveled in the rear and who were expelled by the clouds of glory because they were carrying the idol of Michah, so severely punished?
But we can understand why with a parable about a great king who ruled a great empire and who had an only son, and because this son had all the luxuries of life he unrestrainedly followed the desires of his heart and did many bad things. Consequently the king became very angry at him and drove him out his palace, forcing him to wander in far-off places in order to humble his heart. But whilst he was in those distant places many enemies of the king found him and afflicted him harshly and gave him many troubles, not fearing retribution from the king because they believed that he had distanced his son because he despised him.
But after some time the king remembered his son and sent his carriage to bring him home and return him to his former greatness and glory, and again provided him with all his needs with great love. The son then told his father what his enemies had done to him whilst he was living abroad, and when the king heard this he became very angry and recorded the names of all those who had done evil to his son and arranged for them to be brought to him. He then punished each one according to the amount of evil which he had done - to one he gave a hundred lashes, to another he gave fifty, and so on. And because of this everyone became afraid to do anything to the king’s son.
But there was in the king’s palace an evil man who became very jealous of the king’s son when he saw that he had been restored to greatness and had gotten vengeance from his enemies. He became very angry and in his anger he arose and attacked the king’s son, slapping him on the cheek in front of the king and his ministers. When the king saw this he immediately commanded that he should be severely tortured to death.
After the king’s anger had abated, one of the ministers said to him: Our master, the King, I have a question to ask your Honor - why is it that the other enemies who did much more evil to your son you punished only with a few lashes, yet this evil doer who only slapped his cheek you had killed? The king answered: These others did evil to my son when I drove him away from me into exile, causing them to think that I despised him and had abandoned him. But this man saw my son sitting by my side in great honor, and saw that I loved him and took care of him, and yet he was so brazen as to hit him and disgrace him in my presence! He not only did evil to my son but was a rebel against the kingdom. Therefore, it was fitting that he be punished so severely.
So too the Egyptians and all the other nations did evil to Yisrael whilst they were in exile, at a time when Hashem hid His face from them and distanced them from Him, and thus they thought that Hashem had abandoned them. Therefore He did not punish them so severely. But Amalek saw Hashem’s great love for Yisrael, taking them out of Egypt with signs and wonders and leading them with great honor with the pillar of fire and clouds of glory, and he saw that the fear of Yisrael fell upon all the nations, and even so he brazenly attacked them. Thus, even though he only killed those who were weakened, those who had with them the idol of Michah and were fitting to be punished, nevertheless, since he acted brazenly and rebelled against the King of Kings by attacking His children, Hashem decreed that his name and memory should be erased from the world.
This is what the posuk is saying: “Remember what Amalek did to you”. And when did he do this? “On the way as you went out from Egypt” under Hashem’s care. “How he happened upon you on the way (אשר קרך בדרך)” - Chazal explain that this means “who cooled you down on the way” with a parable about a boiling hot bath that everyone was afraid to enter until someone came and jumped into it to show everyone that it was not as hot as they thought. So too Amalek - when he saw that all the nations were afraid of Yisrael he became jealous and attacked them, thus demonstrating to all the nations not to be afraid of them.
This is the meaning of the continuation of the posuk “and you were exhausted and tired” - he showed all the nations that they were exhausted and tired and were not able to respond to his attack, “and he did not fear G-d” - and with this he acted brazenly and rebelled against Hashem. Therefore his punishment was very severe -“Erase the memory of Amalek from under the heavens!”.