In other words, zachor-remember is the obligation to articulate while lo tishkach-do no forget encompasses latent memory. Thought without articulation is not sufficient to fulfill the positive mitzvah of remembering Amalek, but would qualify as a fulfillment of the negative commandment[1]..

We will revisit this distinction. For a moment, let's move to our first question: Wherein lay Amalek's uniqueness?

A brief exploration of his roots yields a clue. First, the text: [Bereishis, 36:12]

And Timna was a concubine to Eliphaz, son of Esau, and she bore to Eliphaz, Amalek.

Then the Talmud (Sanhedrin 99b)

And Lotan's sister was Timna? - Timna was a royal princess .. Desiring to become a proselyte, she went to Abraham, Isaac and Jacob, but they did not accept her. So she went and became a concubine to Eliphaz the son of Eisav, saying, 'I had rather be a servant to this people than a mistress of another nation.' From her Amalek was descended who afflicted Israel.

Amalek emerges from Eisav, Yisrael's antithesis. Disdaining all things spiritual, Eisav rejects the birthright precisely for its lack of present-worldly value.[2]. But Eisav alone does not create Amalek. His son Eliphaz marries Timna. - a woman who seeks purpose, and is rejected by Avraham. She bonds with Eliphaz. Together they have Amalek. Timna bequeaths to Amalek the gift of passion and purpose. Witness that both Bnei Yisrael and Amalek are called a nation of firsts (reishis)

When he (Bilaam) looked on Amalek,  ..  and said, Amalek was the first of the nations; [Bamidbar, 25:20] 

Israel is holy to the Lord, and the first fruits of His produce; [Yirmiyahu, 2:3]

First, as in primary! Both possess a sense of mission and sacrifice. Rashi's famous midrash declares:  

 They cooled you, moderated you to tepidness from seething heat. For all the nations were afraid of waging war against you, until they commenced, preparing the way for others. This is compared with a boiling bath into which no creature could enter. One villain came and leaped into it. Although he was scalded, he cooled it for the others.

And what does Amalek seek? It's a long story, but here's the upshot: Amalek raison d'etre is to wreak havoc upon faith and the faithful. Amalek's weltanschauung is the random world, perceiving history as a capricious set of events without ultimate rhyme or purpose. Amalek-world champions safek (Doubt); both (Amalek and safek) possess the same gematria (numeric equivalent value = 240); Amalek desires to insinuate doubt in the believer's world and to ultimately sever one's connection with the Divine.

Rabbinic literature thus equates Amalek with yetzer hara and the primordial serpent, the nachash. That which prompts the Amalek reminder immediately before Purim, is the belief in randomness, mikreh - a word that binds Haman to his ancestor Amalek. [Esther, 4:7]

And Mordecai told him of all that had happened to him [karahu]. He said to Hatach: ' Go and say to her: "The descendant of karahu has come upon you,"'

In a random world, reflection, spirituality, morality and all things good are ultimately meaningless. Perhaps a social contract may be necessary but that is pragmatic not philosophical, technical and not fundamental

Finally, Amalek catches us on the road; an utterly trivial statement - unless one considers that it is the road to Sinai! The epic battle between Amalek and Yisrael takes place on our road. Amalek's mission: to get us off the road. For the Jew, our world is a pathway to purpose; for Amalek, the here and now is not a conduit - it is home sweet home. Amalek's antipathy for us is because we transform their homes into our roads - a spiritual eminent domain without compensation!

Here we return to our zachor/al tishkach double obligation:

A friend calls. Struggling in a downward spiral and enmeshed in an unbelievably painful personal reevaluation of his path, he is now on the mend. We speak tachlis! [briefly and sincerely]; he formulates a gem: "The source of all my problems (and there were many) began when I distanced myself from God. When I was down, I always knew God was in my life. Then I felt in control, I told God: I'll take over now. That was the moment it all began to slip away."

Zachor, a verbal repudiation of Amalek requires clarity. In pristine moments, dispelling Amalek is easy, while doubt seems inconceivable. When are those moments? For some, they might come davka amidst a sea of engulfing difficulties so overwhelming that there is only God to turn to. Others find God amidst serenity and simcha. Either way, when God feels close, it is hard to imagine there is any room for Amalek.

Amalek however is patient; it preys on the weak ones and pounces during times of weakness. It is when clarity yields to muddle and pristine to puzzlement, that the Torah mandates lo tishkach[3]. Hold on. You may not be able to see Hashem and articulate the clarity; He might seem so distant, but do not shut Him out.

As we move on to Megillat Esther (the revelation of the hidden), may the inner Amalek, the looming doubts that may plague us mitachat hashamayim, in our this-worldly existence of God's concealment, be defeated!

A Freilichen Purim!

Good Shabbos - Asher Brander