Our Gemara on Amud Aleph and Beis asks why we blow shofar both before Musaf, and then during Musaf, when clearly the fulfillment of the Mitzvah only requires one set of blows? The Gemara offers an odd-sounding reason: In order to confuse Satan. 

I would say we are the ones that are confused, not Satan. In fact, it’s hard to believe that after all these years, Satan falls for the same trick, like Charlie Brown forever trying to punt the ball, while Lucy pulls it away. Let us study this concept of כדי לערבב השטן in the commentaries and other instances when it is invoked to get a better understanding of this. 

Rashi offers a straightforward Peshat, though difficult to understand at face value. Since Satan will see the Jewish people’s love for mitzvos, in that they repeat the mitzvah of Shofar, his accusations will be silenced. 

The difficulty with Rashi’s peshat is that classically the word used for Satan’s accusations are קטגוריא categoria from the Greek κατηγορέω (kategorio) meaning “kata” “to speak” in the “agoreuó” assembly. That is, Satan would speak in the heavenly tribunal. If the Gemara meant that, a better phrase might have been listom piy Hasatan or Listom pi kategoria.

However, an inspiring idea comes out of Rashi’s peshat. That is that one can silence and confound Satan’s accusations by doing other unrelated mitzvos with love and zeal. This is a different route than typical teshuva.

Shem MiShmuel (כי תבא ה) cleverly expands on Rashi’s peshat. He says that if the Jews demonstrate their love for mitzvos, this can induce a state of תשובה מאהבה. And the Gemara (Yoma 86b) tells us that repentance out of love turns sins into merits. Therefore, Satan is worried about finding more sins as this might lead to even more merits!

Perhaps we can use this idea to explain Rashi better. He is not silenced or confused in a typical sense, rather he is afraid to speak. The Hebrew term לערבב means to mix up, as in the “Eiruv Rav”, the mixed multitude. Satan is not really silenced nor is he confused. Rather, since his accusations of sin will only increase the merit, his claims themselves have become intrinsically paradoxical and confused.

Tosafos learns a different peshat in confusing Satan, based on an Aruch, which quotes a Yerushalmi. The second blowing, makes Satan think that it is announcing the arrival of Moshiach, causing him to panic.

Rashba suggests the extra blowing of the shofar will arouse more people to humble themselves and do teshuva. What is difficult about this peshat is why the Gemara resorted to such poetic metaphoric language for a basic idea.

The Kliy Yakkar (Bereishis 22:13) follows the peshat that the extra blowing is a call to do Teshuva and Satan gets nervous that the Jews will actually repent and/or the Maschiach will come. He also asks the obvious question, how do we manage to confuse and fool Satan the same way, year after year? This is where it gets interesting. Kli Yakkar says it’s not because the Satan is caught by surprise, but rather because he is genuinely worried that maybe, this time, the Jewish people will do Teshuva correctly.

A beautiful idea that we can take from this Peshat is that even Satan believes in the power and potential of Teshuva. If he believes in it, so should we.