Why do the episodes of the war with Amalek and Yisro’s arrival serve as lead-ins to the revelation at Sinai and the Decalogue?
Is it better to be shrewd or gullible?
Is there any room for skepticism in the hearts and minds of believers in the 13 Articles of Faith?
And [thus] Yehoshua weakened Amalek and his allies by the sword
— Shemos 17:13
And Yisro priest of Midyan , Moshe’s father-in-law heard about all that Elokim had done for Moshe and His people Yisrael, when He extricated Yisrael from Egypt … And, along with Moshe’s wife and sons, Yisro came to the desert where Moshe was camped near Elokims mountain.
— Shemos 18:1,5
And Yisro … heard: What news did he hear that [motivated him enough] to come? The splitting of the Sea of Reeds and the war with Amalek. —(from Zevachim 116A, and Mechilta)
— Rashi ibid
Now I know that Hashem is the greatest of all the deities, for [He came] upon them [the Egyptians] with the very thing that they plotted.
 — Shemos 18:11
Of all the deities:Â This teaches us that he [Yisro] was familiar with every type of idolatry in the world, and there was no pagan deity that he had not worshipped. (from Mechilta)
— Rashi ibid
Destroy all the places, where the nations that you are driving out served their gods, [whether] upon the high mountains, the hills, or under every verdant tree.
— Devarim 12;2
For your gods were as numerous as the number of your cities, O Judah …
— Yirmiyahu 11:13
… yet upon every high hill and under every leafy tree[traditional places of idols and their worship] you recline, playing the role of a harlot.
— Yirmiyahu 2:20
The naïf believes everything; but the incredulous understands the correct footsteps to tread.
— Mishlei 14:15
Strike the scorner, and the naïf grows shrewd.Â
— Mishlei 19:25
“Strike the scorner†this refers to Amalek “and the naïf grows shrewd†this refers to Yisro
 — Shemos Rabbah Yisro 27
I am HaShem your Elokim who extricated you from the land of Egypt, from the house of slavery
— Shemos 20:2
And he [Bilaam] gazed at Amalek, and took up his allegory, and said: “Amalek is the first among the nations; but his end shall come to eternal destruction.â€
— BeMidbar 24:20
Like fire and atomic energy; faith can be a tremendously positive and constructive or a negative and destructive force. When one has faith in HaShem, true prophets and chachmei haTorah-authentic Torah sages; it sustains and nurtures the life of the faithful, as the pasuk teaches v’tzadik b’emunaso yichyeh-and the just will live in/through his faith (Chavakuk 2:4). However, when faith is invested in false gods, false prophets and/or assorted charlatans, there is nothing more corrosive, detrimental to society and self-destructive. To carry the simile further, just as nations are better served by building safe and secure nuclear power plants than in stockpiling surplus nuclear warheads, one must be extremely judicious and discriminating in deciding what and/or whom to invest their faith in.
So, while faith can potentially be the greatest of virtues, it is not to be confused with gullibility and naïveté. Faith unleavened by healthy doses of discernment and skepticism is folly and, as Yirmiyahu the prophet implies by describing the idolatrous Jews of his era as “playing the harlot†and having as many deities as cities, a kind of promiscuity of the heart and mind. The emunah-faith; of one who has “complete and perfect faith†in the thirteen fundamental articles of Jewish belief is of diminished value if he also believes in every outlandish hoax ever publicized or if he can be swindled into buying the Brooklyn Bridge because he is convinced of the seller’s integrity. For faith in truth and belief in reality to be commendable one must first stop suspending his disbelief in mirages and repudiate the bill-of-goods that he had formerly been convinced of for the lies that they are.
At one time or another Yisro believed in every possible manner of fabrication. Chazal teach us that there was not a single pagan deity that Yisro did not worship. To buy in to so much and such varied deception means that Yisro was possessed of an extremely credulous and gullible nature. The lashon kodesh-biblical Hebrew; word that defines this kind of folly is pessi-a naïf who’ll believe anything.
At the extreme opposite pole of human nature stands the letz-scorner/scoffer who believes in nothing and no one. Such people wear their incredulous disbelief as badges of honor marking them as wiser and as sharper than the credulous. They scoff at believers, first and foremost by mocking all that they believe in. Such skeptics scorn across the board and no target is safe from their sneering, scathing “appraisals.†Such letzim are the Wildean cynics who “know the price of everything and the value of nothing.â€
Amalek is identified by Chazal as the letz incarnate. The national character of Amalek is wired to scoff and mock everything, up to and including all that is real, true and holy. How else can we understand that while all other nations were awestruck by the events of the Exodus from Egypt and the Parting of the Sea of Reeds, so much so that they had come to some level of belief in the invincibility-borne-of-chosen-ness of the Bnei Yisrael-the Jewish people; and the Infinite Power of the G-d of Israel, Amalek remained unimpressed? The preemptive attack launched by Amalek was their über-skeptical “I’m from Missouri, you’ve got to show me†moment.
The Izhbitzer explains that once letzim are inevitably set in evil ways they become irredeemable. All exhortations to tikkun-repairing ones evil; depend on getting the perpetrator to believe in the value of change and improvement. But the scoffing, scornful, skeptical letz does not recognize or tolerate chashivus-value and significance. One can try to rehabilitate the letz with both high-minded arguments and/or corporal-punishment “convincing†and both will be wasted on those who know the value of nothing. On the other hand, when dealing with a pessi there is someone to talk to and something to work with. The ethical challenge of the pessi is that he believes in the value of too many things. Discernment and a healthy dose of skepticism come with experience and education, sometimes even from education gleaned from the lessons and exhortations wasted on the letz.
This, says the Izhbitzer, is why the Midrash teaches that “the scorner†refers to Amalek and that “the naïf†refers to Yisro. We are instructed to annihilate Amalek because nothing good will ever come of that nation. Amalek lacks the capacity to believe and to value and thus can never change or grow. The Izhbitzer interprets the instruction to “strike the scorner†not as a means of training the scorner or to impress the value of what he is lacking upon him — but to strike him dead in order to purge his irredeemable evil. While Yisro was indeed a naïf who was sold a theological Brooklyn Bridge, his credulity was informed by awe, reverence and the recognition of value to the point of self-abnegation and worshipfulness. He was a seeker of truth who’d been too rash and trusting; believing all the pretenders to the truth. He grew incredulous of these imposters when he finally glimpsed “the genuine article†— HaShem’s Greatness manifested through, among other wonders, the Striking of Amalek.
At first glance a letz may appear sharper and even wiser than a pessi. But at the end of the day, and at the End-of-Days, it is far better to be a pessi than a letz for a pessi can grow more incredulous and skeptical and come to know that Hashem is the greatest of all the deities. As was the case with Yisro, any pessi can become a convert to the truth.
The Izhbitzers disciple Rav Tzadok, the Lubliner Kohen, elaborates on the evil of leitzanus-the mocking, scornful incredulity of the letz and in so doing sheds light on why the contrasting narratives of the weakening of Amalek and Yisro’s arrival and conversion, serve as the hakdamah-preface; to the aseres hadibros-the Decalogue.
Many commentaries have pointed out that the first of the ten “commandments†is not a command at all, but a statement of fact, a Divine Calling Card or a Divine Job-Description. This, the Lubliner Kohen teaches, is because faith in HaShem is the foundation upon which all the other commandments … all that is good, is built. It is the gateway to mitzvos but is qualitatively different from mitzvos. Just as faith and credulity in HaShem’s “Right†to command is the gateway to all that is virtuous; scorn, skepticism and incredulity, in a word; leitzanus, is the root of, and gateway to, all evil and iniquity. Just as there cannot be a positive commandment “Thou shalt believe in HaShem†there can be no negative commandment “Thou shalt not be a letz.†One is either credulous of the truth of HaShem and His Adnus-L-rdship and Right to command; or incredulous and scornful of the notion. Until and unless one believes in HaShem and has accepted His Adnus all commandments will be viewed as non-binding nonsense.
In his prophecy Bilaam describes Amalek as the “first of the nations.†The Lubliner Kohen interprets this sobriquet to mean that the letz national character of Amalek is the beginning, the very nascence of all powers of, and capacity for, evil.
The Rebbe Reb Henoch of Alexander taught that “the line dividing good merirus-world-weariness; from evil atzvus-depression; is no wider than a hairsbreadth but that hairsbreadth is itself the gaping chasm separating heaven from hell.â€Â In light of the teachings of the Izhbitzer school concerning the letz and the pessi we might say that the line dividing healthy skepticism in, and dismissiveness of, all powers and “gods†except for the Single, One True G-d from soul-sickly nihilism, and the inability to believe in any powers and “gods†with NO exceptions at all, chas v’shalom-Heaven forfend; is no wider than a hairsbreadth but that hairsbreadth is itself the endless difference between tikun-a presence in eternity;  and avdon-eternal annihilation and nonexistence.
Â
~adapted from Mei Hashiloach II Yisro the third Dâ€H Vayisham Yisro
and Tzidkas Hatzaddik 259
there is first in chronology and first in causality.
the letz national character of Amalek is the beginning, the very nascence of all powers of, and capacity for, evil.
Nimrod, Yishmael, Esav and Lavan surely preceded Amalek in evil, yet I imagine the evil of Amalek was that he graduated from being a lone wolf, to state sponsored (entire nation) terrorism.