What is the meaning of "Asher Korcha ba'Derech"?
Rashi #1, Rashbam, Targum Onkelos and Targum Yonasan: It means 'who encountered you on the way'.
Rashi #2: It means 'who defiled you ... ' - from the word 'Keri' (semen) - with homosexuality.
Rashi #3: It means 'who cooled you down from your heat ... ', 1 because the nations were afraid to fight with you [after hearing about Keri'as Yam Suf], and when he came and attacked you, he paved the way for others to follow suit.
Malbim (in Pasuk 17): It implies that they did not attack you to conquer land, or in defense of their own land - since they attacked whilst you were travelling. (Refer to 25:19:152:1)
With reference to the excitement with which they left Egypt in order to receive the Torah on Har Sinai. See Oznayim la'Torah. Rashi: The Torah is in fact, alluding to a comparison to a hot bath that nobody dared enter, until a good-for-nothing came and jumped in. He may well have scorched himself, but he cooled it down for others to take the plunge.
What is the meaning of "va'Yezanev b'cha"?
Rashi and Targum Yonasan #1: It means 'And he smote the tails' - he cut off their Milos 1 and threw them into the air'. 2
Targum Onkelos and Targum Yonasan #2: It means 'He killed from among you ... '.
Why did Amalek choose to defile Yisrael specifically in connection with the Milah?
Oznayim la'Torah: Because, before Matan Torah, the Mitzvah of Milah was what distinguished Yisrael from the other nations. So Amalek decided at one and the same time, to insult Hashem and defile Yisrael. Also because the descendants of Eisav believed that without B'ris Milah, one cannot learn Torah. Consequently, he set out to prevent Yisrael from accepting the Torah - 'by cooling them down' - whilst they were at the last stop before Matan Torah,and giving vent to his anger at the impending event in this way. 1
See Oznayim la'Torah, who elaborates.
What are the connotations of "Kol ha'Necheshalim Acharecha"?
Rashi #1 (citing the Tanchuma): It refers to those who were weak 1 due to their sins and whom the Cloud cast out.
Rashi #2 in Yechezkel, 16:15 (citing the Pesikta) and Targum Yonasan: It refers to members of the tribe of Dan, whom the Cloud expelled, since they (all - Rashi) worshipped Avodah Zarah. 2
Malbim (in Pasuk 17): It implies that Amalek did not atack you to demonstrate his strength - seeing as they attacked the weakest of Yisrael. (Refer to 25:19:152:1)
See Torah Temimah, note 203.
Targum Yonason: They were the strong men of the tribe of Dan who had in mind to stray from Hashem's words and who had with them the image of Michah. Refer to Shemos, 17:8:1:3* & 14:29:2:1.
What are the connotations of "ve'Atah Ayef ve'Yage'a"?
Rashi: It means 'You were thirsty and weary - from the journey'. 1
Targum Onkelos and Targum Yonasan: It means 'You were tired and weary' 2 (from the harsh slavery in Egypt and from the fear of the waves of the Yam-Suf which Yisrael passed through - Targum Yonasan).
What are the ramifications of "ve'Lo Yarei Elokim"?
Rashi: Amalek attacked Yisrael because they (Amalek) were not afraid of Hashem. 1
Chizkuni (citing an opinion in the Mechilta): Had Yisrael feared Hashem, Amalek would not have been able [to harm them]. Also refer to 25:17:1:2.
Malbim (in Pasuk 17): Do not say that they fought you to find favor in the eyes of their god by destroying those who do not believe in it, because Amalek did not fear Elokim. 2 (Refer to 25:19:152:3)
In spite of all the miracles ? or perhaps in defiance of all the miracles ? that Hashem had performed on their behalf.
Not Hashem, nor any other god. Alshich (Tehilim 68:31): Amalek caused Yisrael to sin with idolatry more than any other nation. Haman had an idol over his heart (Esther Rabah 7:5). Pirkei d'R. Eliezer (50) calls it 'his abomination', which implies that he served it [and did not intend merely to make others bow to idolatry]. Perhaps the Malbim holds like R. Tzadok ha'Kohen (Takanas ha'Shavin p.31) that Amalek is "Reishis Goyim" - the source of the idolatry of all nations; they pride themselves in their own strength, and deny that it is from Hashem. (Haman made himself an idolatry ? Megilah 10b. Teshuvos ve'Hanhagos (4, Hanhagos ha'Grach 104) explins that Amalek were not merely idolaters; they were total deniers of Hashem and His Hashgachah? who believed that everything happens by chance! If so, they could not have fought Yisrael to find favor in the eyes of their god. ? PF)