We don’t bensch Rosh Chodesh on the Shabbos preceding Rosh Hashana as we do before every other Rosh Chodesh. There are numerous reasons given but the most frequently quoted reason is that by doing something different, we hope the Satan will become confused as to when Rosh Hashana falls out and forget to prosecute. It is for this reason as well that we do not blow the shofar after davening on Erev Rosh Hashana as we have been doing throughout the entire month of Elul.
The Rambam talks about the punishment Egypt suffered for having enslaved the Jews. A very compelling and powerful question is, why is Egypt held accountable to the point where they not only get punished with ten plagues, but they are drowned and ultimately all but eradicated from the face of the earth? Hashem dictated to Avraham Avinu long before there were any Jews in Egypt that due to one some very significant reasons (either because of a sin or because of the impact servitude would have on Klal Yisroel), that they would be strangers in a land not their own, slaves and afflicted. The Rambam explains that G-d did not mandate that it had to be Egypt; they elected to be G-d’s instrument of pain. Other commentaries add the observation that Egypt went beyond the call of duty and they enjoyed it too much. Having the license to afflict Klal Yisroel did not give them the right to do all of the excessively brutal things that they did. So we see that Egypt was not interested in fulfilling G-d’s word rather they did it in their hatred of G-d’s word and in their hatred of Klal Yisroel as His elect people. They abused this license to express their detestation for G-d and everything Klal Yisroel represented.
Symptomatic of disinterest in fulfilling G-d’s will is being excessive or overly zealous in evil which reveals the true impetus behind their apparent attempt to help with G-d’s mission. Evil will defend itself by saying, “But we were doing what you wanted us to do.”
There is a famous comment made by the Baal Shem Hakadosh. The Gemora tells us that at the end of time, Hashem will slaughter the Satan and all of the forces of evil. The question we mentioned above regarding Egypt is applicable here on a much broader level. G-d commissioned Evil to tempt us, to confuse us and to ultimately test our faith and love of Hashem. Why is Evil held accountable at the end of time for doing exactly what Hashem said to do? Evil does something very important. The whole concept of bechira, free choice, revolves around the existence of Evil.
The answer is because Evil did not follow his instructions exactly.
There is a Mishna in Masechta Shabbos which states that it is a violation of Shabbos to shecht an animal. The Gemora ultimately concludes that the malachah, form of work, transgressed is tzevia, dyeing, because the blood of the animal colors the hide. On the question of the Gemora השוחט אמאי מיחייב - "For what is the one who slaughters culpable?", Tosfos says השוחט דעלמא - "an ordinary shechting".
So the Baal Shem Tov says that this referring to the Shochet of the World, namely the Satan. He’s the one who descends to seduce man to evil, as a result of which he ascends to prosecute against man. He then has the right to go down and punish the person for having done evil. הוא השטן הוא היצר הרע הוא המלאך המות - "The Satan is the Evil Inclination and the Angel of Death".
So the Gemora is asking, says the Baal Shem Tov, why is this Satan subject to prosecution at the end of history (as Chazal tell us that the Satan will be slaughtered)? The Gemora answers that he is chayav because of dyeing. He had the right to go down and tempt man but he was not given license to distort the truth. The yetzer hara tells man, in a certain instance, that it is a mitzvah to speak loshon hara about someone who isn’t all that righteous (which is absolutely not the case). The Satan takes aveiros and masquerades them as mitzvos. If he would convince man to go eat shrimp even though it is forbidden then he would have done his job, but to misrepresent an aveira and paint it as a mitzvah (or vice versa), for that he will be held accountable. The Satan went beyond its legitimate scope by presenting man with too many choices that were more compelling than Hashem desired.
Evil has established its own empire. Its greed, its lust for power, its perception that it can expand its minions of emissaries by bringing more and more evil into the world, is the illusion that Evil “suffers” from. Evil knows it can only be sustained by G-d but it has license to operate on its own.
There is a concept of יודעים את רבונם ומכוונים למרוד בו - "One who knows his Master, yet intends to rebel against Him". The frame of reference of those who choose Evil is understanding that the Master is sovereign and yet choosing to defy Him. Evil’s appetite for power has extended its domain far beyond its legitimate bounds.
Now, the Satan is aware that there is an era of accountability and that an era will arrive when his dominion will be terminated. It is etched into the mind of Evil by the Akeida, where the first shofar came into being, and by Har Sinai where Jews were for a brief period of time liberated from the influence of Evil - that extirpation of Evil from the world will be announced by the sound of the shofar: והיה ביום ההוא יתקע בשופר גדול - "And it will be in that day, a Great Shofar will be blown". That’s the end of all Evil and death.
The minute we start sounding the shofar, as many times as it’s done, the Satan knows that one of these time it’s going to be for real. Despite the fact that we’ve been sounding the shofar again and again, but eventually the shoe is going to drop. One of these days, the blowing of the shofar will usher in Moshiach and the slaughter of Evil.
There are two things that rattle and confound the Satan; one of which is the sound of the shofar. The other is that when Moshiach comes we will no longer calculate our calendar by a mathematical computation but by the new moon and the Sanhedrin.
As the month of Tishrei approaches, we don’t announce when the new month is. Of course, he could go into a store and buy a luach if he wanted to. But it isn't a matter of forgetting, rather of being reminded. The very fact that we didn’t announce the month is because we are looking towards that time when we won’t be able to announce the month until it is sighted. It is unsettling for the Satan because he knows what’s going to happen when Moshiach comes. He is reminded there is an opportunity for a new judgment and G-d may very well decide this is it and Evil’s reign will end. He knows when Rosh Hashana is, but in the absence of the shofar and the Blessing of the New Month, he hears Pavlov’s bell and thinks, "This is a forerunner when my time is up". He knows very well what day it is. It is that knowledge and the reminder of what this day could be that confounds him.
The shofar that we blow on Rosh Hashana is the shofar of the Akeida, of Har Sinai and ultimately the shofar of Moshiach. The Satan knows what’s coming: a time without Birkas Hachodesh, a time of when that final blast of the shofar will be sounded and that means time when he is called up for judgment for having exceeded his mission. And that’s when the Satan finds himself in a place where he’s confused if he should be so passionate about prosecuting and not exactly sure what he should do now.
May we merit that the prosecuting angels be confused and that we all emerge victorious in judgment with the Ultimate Victory, the decommissioning of the Satan and his conglomerate of Evil, pain and death, and with the coming of Moshiach, speedily and in our days.
(Erev Rosh Hashana, after Shachris, 5766)
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