The figure of Amalek (first mentioned in Genesis 14:17) gives us a specific insight as his persecution of Israel. Amalek is directly tied to "doubt" (versus faith) on the part of God's people. When the Hebrew people doubt God, Amalek strikes. In gammatria, the numerical value of "Amalek" (240) and the word for "doubt" (safek) are the same.
We begin with a short citation from the Midrash on Numbers:
Midrash Rabbah - Numbers XIX:20 - The Amalekites were ever a strap of chastisement for Israel. You find that as soon as they said, Is the Lord among us? (Deuteronomy 17:7), Came Amalek (ib. 8). When They said one to another: Let us make a captain, and let us return into Egypt (Num. XIV, 4), Then the Amalakite and the Canaanite... came down (ib. 45).
The Zohar offers a similar view:
Soncino Zohar, Shemoth, Section 2, Page 65b-66a - When a young man who lives at ease in his father's house begins to make all sorts of complaints and demands, saying, I want this, and I do not want that, he attaches himself to that sore evil, and he will be punished both in this world and in the world to come. Concerning such a case, King Solomon said: There is a sore evil... riches kept for the owners thereof to their hurt. Such was the case of the Israelites: the Holy One, blessed be He, carried them on eagles wings, encircled them with the clouds of glory, made the Shekinah go before them, gave them manna to eat, and sweet water to drink, and yet they complained! Hence, and Amalek came."
The idea of "doubt" being a critical sin was actually brought up earlier in John's vision:
Revelation 3:15-16 - I know your works, that you are neither cold nor hot. I could wish you were cold or hot. So then, because you are lukewarm, and neither cold nor hot, I will vomit you out of My mouth.
These ideas of doubt and lukewarmness, as connected to Amalek, are said to infect the Jewish people at certain times in history, one being at the time of the sin of the golden calf:
Soncino Zohar, Bereshith, Section 1, Page 28b - The mixed multitude are the impurity which the serpent injected into Eve. From this impurity came forth Cain, who killed Abel.... From Cain was descended Jethro, the father-in-law of Moses, as it is written, And the sons of the Kenite the father-in-law of Moses (Jud. I, 16), and according to tradition he was called Kenite because he originated from Cain. Moses, in order to screen the reproach of his father-in-law, sought to convert the mixed multitude (the descendants of Cain), although God warned him, saying, They are of an evil stock; beware of them. Through them Moses was banished from his proper place and was not privileged to enter the land of Israel, for through them he sinned in striking the rock when he was told to speak to it (Num. XX, 8); it was they who brought him to this. And withal God takes account of a good motive, and since Moses motive in converting them was good, as has been said, therefore God said to him, I shall make thee a nation greater and mightier than he (Ibid. XIV, 12). In regard to them it is written, Whoso hath sinned against me, him will I blot out of my book (Ex. XXXII, 33), for they are of the seed of Amalek, of whom it is said, thou shalt blot out the memory of Amalek (Deut. XXV, 19): it was they who caused the two tablets of the Law to be broken.
Amalek's power is traced directly to the serpent, the master of planting doubt in the minds of humans (i.e, such as in the Garden of Eden story).
"What does DOR DOR (from generation to generation) mean? Amalek the wicked comes from the power of the primordial snake, and it is there that he connects and draws his strength." 4
Amalek is directly associated with Samael, the archangel of evil. He is the cause of the "three great sins" -- idolatry, murder and unchastity (sexual sin):
Soncino Zohar, Bereshith, Section 1, Page 28b,29a - Various impurities are mingled in the composition of Israel, like animals among men. One kind is from the side of the serpent; another from the side of the Gentiles, who are compared to the beasts of the field; another from the side of mazikin (goblins), for the souls of the wicked are literally the mazikin (goblins) of the world; and there is an impurity from the side of the demons and evil spirits; and there is none so cursed among them as Amalek, who is the evil serpent, the strange god. He is the cause of all unchastity and murder, and his twin-soul is the poison of idolatry, the two together being called Samael (lit. poison-god). There is more than one Samael, and they are not all equal, but this side of the serpent is accursed above all of them.
The three sins of idolatry, murder and unchastity are those for which a Jew is expected to give up his life. In other cases, it is permitted to sin if one's life is at stake:
Talmud, Sanhedrin 74a - R. Johanan said in the name of R. Simeon b. Jehozadak: By a majority vote, it was resolved in the upper chambers of the house of Nithza in Lydda18 that in every [other] law of the Torah, if a man is commanded: Transgress and suffer not death he may transgress and not suffer death, excepting idolatry, incest, [which includes adultery] and murder.
These three sins are said to be what caused the destruction of the first temple:
Talmud, Yoma 9b - Why was the first Sanctuary destroyed? Because of three [evil] things which prevailed there: idolatry, immorality, bloodshed.
(See Revelation 9:21 which adds "theft" to these others.)
The greatness of Amalek's power is seen in this commentary on Israel's war with with him:
Soncino Zohar, Shemoth, Section 2,Page 66a - R. Simeon said: There is a deep allusion in the name Rephidim. This war emanated from the attribute of Severe Judgement and it was a war above and a war below. The Holy One, as it were, said: when Israel is worthy below My power prevails in the universe; but when Israel is found to be unworthy she weakens My power above, and the power of severe judgement predominates in the world. So here, Amalek came and fought with Israel in Rephidim, because the Israelites were weak (raphe) in the study of the Torah, as we have explained on another occasion. AND MOSES SAID UNTO JOSHUA, CHOOSE US OUT MEN, AND GO OUT, FIGHT WITH AMALEK. Why did Moses abstain from fighting the first battle which God Himself commanded? Because he was able to divine the true meaning of his Master's command. Hence he said: I will prepare myself for the war above, and thou, Joshua, prepare thyself for the war below. This is the meaning of the words :When Moses lifted up his hand, Israel prevailed (Ibid. v, 11), namely Israel above. Therefore Moses did not participate in the war on earth, so that he might throw himself with greater zeal into the war in Heaven, and thus promote victory on earth. Said R. Simeon: Let us not think lightly of this war with Amalek. Verily, from the creation of the world until then, and since then till the coming of the Messiah, there has been and will be no war like that, nor can even the war of Gog and Magog be compared with it; and this not because of the mighty armies taking part in it, but because it was launched against all the attributes of the Holy One, blessed be He. AND MOSES SAID TO JOSHUA. Why to him, who was then but a youth (Ex. XXXIII, 11)? Were there in Israel no greater warriors than Joshua? The reason was that Moses in his wisdom was aware that it was not going to be merely a battle against flesh and blood, but against Samael, who was coming down to assist Amalek. Now Joshua, the youth, had reached at that time a high degree of spiritual perception, not, indeed, as high as Moses, who was united with the Shekinah, but his soul was, in fact, attached to the supernal region called Youth (=Metatron). Now when Moses perceived that Samael was going to fight for Amalek, he thought: this young man, Joshua, will surely stand against him and prevail, and therefore he said unto him: go and fight against Amalek! It is thy battle, the battle here below, and I will prepare myself for the battle above. Choose worthy men, righteous and the sons of the righteous, to accompany thee. Said R. Simeon: At the moment when Joshua, the young man, started out to fight Amalek, the Young Man above was stirred, and was equipped with weapons prepared by his Mother (the Shekinah) for the battle in order to avenge the covenant (cf. Lev. XXVI, 25) with the sword (Ex. XVII, 13). Moses equipped himself for the war above. His hands were heavy (Ibid. v, 12), that is to say, weighty, honourable, holy hands, that had never been defiled, hands worthy to wage the war above. AND THEY TOOK A STONE AND PUT IT UNDER HIM AND HE SAT THEREON: to participate in the distress of Israel.
The Talmud equates the elevation of Moses' hands in the battle against Amalek with faith on the part of Israel (and conversely, the lowering of his hands with their doubt):
Talmud, Rosh Hashana 29a - Now did the hands of Moses wage war or crush the enemy? Not so; only the text signifies that so long as Israel turned their thoughts above and subjected their hearts to their father in heaven they prevailed, but otherwise they fell.
Although Amalek was killed long ago, the Torah and other writings testify to the idea that the spirit of Amalek will not be done away with until the coming of Messiah:
Soncino Zohar, Bereshith, Section 1, Page 25b - But withal redemption will not be complete until Amalek will be exterminated, for against Amalek the oath was taken that the Lord will have war against Amalek from generation to generation (Ex. XVII,16).
The following passage associates the coming of Amalek with the union of two evil spiritual forces coming together. This text also portrays the brazenness of Amalek as having no regard for God whatsoever:
Soncino Zohar, Shemoth, Section 2,Page 65a - And this is the meaning of the words, blessed are ye that sow beside all waters, that send forth thither the feet of the ox and the ass, namely, the two Crowns of the Left, to which are attached the pagan nations who are called ox and ass. When the Israelites are worthy, then they dismiss these evil powers, and they have no dominion over them. Said R. Abba: When the two (i.e. the ox and the ass) are united, the inhabitants of the world cannot stand up against them. For this reason it is prohibited to plough with an ox and an ass together (Deut. XXII, 10). From them, when united, emanates the power, called dog, which is more insolent than all of them. Said the Holy One, blessed be He: Ye said, is the Lord in our midst or not? Behold, I will deliver you to the dog!, and straightway came Amalek. R. Judah said: It is written, Amalek is the first of the nations; but his latter end shall be that he perish for ever (Num. XXIV, 20). Was, then, Amalek the first of the nations? Were there not many tribes, nations, and peoples in the world before Amalek came? But the meaning is that Amalek was the first nation who feared not to proclaim war against Israel, as it says, and he feared not God (Deut. XXIV, 18); whilst the other nations were filled with fear and trembling before Israel at the time of the Exodus, as it says: The peoples heard and were afraid; trembling took hold of the inhabitants of Pelesheth (Ex. xv, 14); in fact, apart from Amalek there was no nation that was not awestruck before the mighty works of the Holy One, blessed be He. Therefore his latter end shall be that he perish for ever.
As mentioned throughout this study, the cure for Israel's woes is the Torah:
The Torah says: "Amalek battled Israel in (a place called) Refidim" (Exodus 17:8). The Midrash explains that the name "Refidim" is a contraction of Hebrew words meaning "they loosened their grip on Torah." As long as the Jews were diligent in Torah study, Amalek had no dominion over them. But as soon as Jewish study became lax, they were in danger. 5
We can now make the following contrasts and comparisons:
Thus "doubt," caused by lack of Torah study, is a tactic used by the enemy to prevent the "completion" of the Temple/Throne of God and the unification of His Name. Anything that disuades people from being "hearers and doers" of the Torah is of Amalek and the anti-Messiah.
A modern teacher/author ties this all together as follows:
When the Beit HaMikdash was eventually constructed on the holy mountain, symbolizing the possibility of human connection with God and holiness, its spiritual foundations are traced back to the prayers Moshe uttered on that hill in the desert. In the aftermath of that first battle we are told that until Amalek is ultimately and completely defeated, something will remain missing in this world and the celestial spheres (Exodus 17:14-16) ... for as long as Amalek is around, spewing his venom, the throne of God and God's Name are, as it were, incomplete. Evil has a foothold in this world as long as God's holiness is not completely manifest. The symbol of the destruction of evil is the final victory in the epic battle with Amalek. Yerusshlayim (Jerusalem) represents God's throne on earth; Amalek represents the attack on the throne. 6
4. Sha'are Orah (Gates of Light) Rabbi Joseph Gikatilla, English translation by Avi Weinstein, Altamira Press, London, 1994, p. 320.
5. From http://www.aish.com/purimthemes/purimthemesdefault/Haman_Heir_to_Amalek.asp
6. Emanations: In-depth analysis of the Jewish holidays through the prism of rabbinic perspective, Ari D. Kahn, Targum/Feldheim, 2002, p. 114.