Where did Amalek come from?
Targum Yonasan: He came from the land of the south - traveling sixteen hundred Mil on one night (using withcraft) to attack Yisrael.
Why did Amalek attack Yisrael at this juncture? What had Yisrael done wrong?
Rashi: 'Hashem is always close to You, to help you in time of need, and you turn round and ask "ha'Yesh Hashem b'Kirbeinu, Im Ayin"?! By your life, the dog will come and bite you, and you will cry out to Me. Then you will know where I am." 1
Seforno: He came because there was strife, and he took advantage of the fact that they were thirsty.
Targum Yonasan: He came on account of the quarrel between Yaakov and Esav, and attacked the Bnei Dan, whom the Cloud had expelled from the camp on account of the Avodah Zarah 2 that they were carrying with them.
Mechilta: Because they were lax in learning Torah. 3
Rashi: This can be compared to a father traveling along the road with his son on his shoulders (corresponding to "Al Kanfei Neharim" - Lev Eliyahu p. 108). When the boy saw something lying on the street, he asked his father to give it to him and his father complied. This happened a second time and a third time. Then as a man came towards them, the son asked him whether he had seen his father. 'What,' his father exclaimed angrily, 'You don't know where I am!' So he threw him down and a dog came and bit him.
With reference to the image of Michah - See Peirush Yonasan. See also Ba'al ha'Turim,
Refidim is an acronym for 'Rafu Yadayim - mi'Divrei Torah' (they were lax - in learning Torah). See also the last Ba'al ha'Turim in Ki Seitzei.
Why did Amalek not attack Yisrael on their way down to Egypt, when they numbered only seventy souls?
Because at that stage, they hadn't yet sinned. Refer to 17:8:1 .
Da'as Zekenim: Because he realized that, once Yitzchak died, the fulfillment of the prophecy "va'Avadum v'Inu Osam Arba Me'os Shanah"(Bereishis 15:13) would fall upon Yaakov as well as Esav, and their children. He realized that were he to kill Yaakov and his descendants, the onus would fall entirely upon Esav and his children. So he waited until Yaakov's children had 'paid the debt,' before attacking. 1
Amalek's grandfather Esav, did a similar thing (refer to Bereishis 36:6:3:2*). See also Chizkuni.
Seeing as Yisrael were surrounded by the Ananei ha'Kavod, how could Amalek attack them?
Rashi (to Devarim 25:18), and Pirkei d'R. Eliezer 44: Amalek killed the sinners whom the Cloud had expelled from the camp.
Mechilta and Shemos Rabah 26:3: Amalek entered under the corners of the clouds, 1 and kidnapped Yisra'elim and killed them. 2
Refer to 17:8:1:3.
Pesikta Rabasi 12: Amalek had a list of the names of those who left Egypt. They called out 'Peloni, come out - I want to do business with you!' When he came, Amalek killed him. 3
Rosh Hashanah 3a : And the reason that they attacked only when, following Aharon's death, the clouds departed - refer to Bamidbar 21:1:1:1 - was because it looked like Divine permission to fight Yisrael.
As the Pasuk hints when it writes in Parshas Ki Seitzei, "va'Yezanev Becha Kol ha'Necheshalim Acharecha" (Devarim 25:18).
Thus, we read "Asher Karecha ba'Derech" (Devarim 25:18 - who happened upon you), as if it had written 'Asher Kara'acha ... ' (he called you).
