Amalek was not the only nation that attacked the Jews. The Canaanites, Sichon and Og also acted in much the same reprehensible manner. Yet, Amalek is the only one about whom the Torah attests was V’lo yarei Elokim, “And he did not fear G-d.” Why is Amalek singled out more than any other one of our enemies, in terms of being unafraid of G-d? The Brisker Rav, zl, explains this, basing his thesis on a statement of Rabbi Yochanan ben Zakkai in the Talmud Bava Kamma 79b. The students of the great Tanna asked him why the Torah is more stringent concerning the punishment of a ganav, thief, than a gazlan, armed robber. He explained that a thief steals at night because he fears being caught. Thus, he indicates that he has greater fear of human exposure than of Heaven. He is afraid of getting caught. Yet, he is unconcerned that he is performing a sin. The gazlan fears no one – neither man, nor Hashem.
Should it not be the other way around? The gazlan is audacious, showing no fear of anyone. His resolute chutzpah shows that he neither cares what people think, nor is he afraid of what they might do to him. The ganav, on the other hand, shows some humility, an element of shame. He is embarrassed about what he is doing and, therefore, does not want to be caught. It would make sense that humility should be rewarded and audacity punished.
The Rav explains that the differences lie in their individual attitude toward life. The gazlan is a person who lives life as it comes. He cares about nothing and does not bother with cheshbonos, calculations. When he is in the mood of acting, he acts. When he is in the mood of taking it easy, he takes it easy. Nothing seems to faze him. He lives an unabashed life, totally unflustered by anything that comes his way.
Not so, the ganav. The thief has a plan. He is cunning and deliberate. He knows exactly what he wants and how to get it – without getting caught. He makes all kinds of calculations, so that he can pull off this job smoothly, without too much effort and with no grief in the aftermath. The ganav is a thinking man who knows what he is doing, because he has it all planned out. Hashem takes umbrage against such a person. If he is so meticulous in his planning, why did he not concern himself with Hashem’s Torah, in which the Almighty commanded that one should not steal? In this sense, the ganav exhibits greater malevolence than does the gazlan, who demonstrates his lack of aforethought.
This is the idea behind Amalek’s being regarded as, “he did not fear G-d.” The other nations battled without cheshbon, caring less about what has happened to them and more about inflicting lasting damage on the ranks of Klal Yisrael. Amalek, however, was astute and meticulous. He waited until Klal Yisrael was tired, wasted from the sudden liberation and transformation from persecuted slave to world traveler in a wilderness that was both harsh and unforgiving. He saw also that their recent commitment to Torah had begun to wane. Now was the time to attack. A battle at this point would prove successful. If Amalek was so thoughtful in his attack on the Jewish People, why did he not consider Hashem, Who was their Redeemer and Protector? It must be because of one reason: v’lo yarei Elokim. He simply did not care, because he did not fear Hashem. Such a nation had broken all barriers. His blatant disregard for the Almighty warranted the appellation for him and his nefarious descendants, of milchamah l’Hashem b’Amalek midor dor, “A war between Hashem and Amalek throughout the generations.”