There is a debate in the Talmud about a question that should be interesting to all of us who will attempt the holy work of teshuvah this Yom Kippur. In Yoma 86b, there is a back and forth about whether or not it is good to mention sins one has committed, confessed for, done one’s best to repent for on a previous Yom Kippur, and not committed again since then. The argument against seems relatively straightforward to me: If we truly believe in the atoning power of Yom Kippur, then when we really do our best to atone, we believe that atonement is accepted. Not only are we under no obligation to return again and again to the worst things we have done, but it actually can be spiritually counterproductive. So much of the power of Yom Kippur is bound up in the core tenet of our tradition that we really do accept that people can change. 

The other side of the argument is subtler and I think offers us constructive insight into the work we must do when we atone. When the Zohar describes, perhaps the ultimate penitent, King David’s relations to his own past mistakes it tells us  “…although he confessed his sin and repented, he could not push from his heart the sins that he had committed, especially of that concerning Bat-Sheba, and was always apprehensive lest one of them would prove a stumbling-block to him in the hour of danger.” (Zohar 1:73b) The Zohar is telling us that David really did repent for the terrible sin he committed, but even though he hoped he had been forgiven for the specific act, he worried that it revealed a real fault within him and that in a hard moment, the same impulse would arise in him and he would make a similar mistake again. The Zohar describes David in this way, I think, to tell us the value of re-repenting. It is not about wiping away the slate on individual moments of falling short, but rather about working through the root causes of those failures to make more and more progress as people each year. 

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At the risk of projecting my own shortcomings onto us all, I want to suggest that this approach to teshuvah keeps in mind that while we don’t make the same mistakes each year, the mistakes we make come from similar places. With that understanding in mind, we are able to approach the liturgy of repentance as a way of approaching the struggles at the core of our being, rather than just feeling guilt for discrete acts of harm. 

With this paradigm of repentance in mind, we can work through another Yom Kippur puzzle. The Sifra, a 3rd-century midrash, tells us that on Yom Kippur our sacrifices atone for two additional national sins, the sale of Joseph and the sin of the Golden Calf. As any reader of the Torah or student of Jewish history can tell you, there have been many failings by our people. Why are these two singled out by the midrash for rectifying on Yom Kippur? Furthermore, both of those incidents were followed by genuine acts of teshuvah, where there seemed to be divine forgiveness after a fashion. Why would these sins need to be dredged up and atoned for year after year? 

I will leave it to others to examine the roots of the Golden Calf elsewhere and instead focus on the sale of Joseph. Given the model of re-repentence discussed above, I think we return to this sin again and again because, like David, we know it reveals a real fault within us, one we must work through before we can stop atoning for it year after year. What share in the sale of Joseph do we have today? A midrash tells us that Joseph was sold into slavery for only 20 pieces of silver, which, when divided among the brothers, was just enough for them to buy themselves a pair of shoes each. The brothers sold Joseph into what they knew would be a brutal life of slavery in order to make themselves more comfortable. 

If only I could say that this sin was unimaginable in our world or communities today. Disregarding the suffering of others, or actively causing their exploitation so that each of us can be just a little more comfortable, is sadly a cornerstone of our society and economic system. Each of us who has benefited from same-day shipping on Amazon, or a thousand other small acts of convenience, plays a tiny part in pushing our siblings into the pit. We atone every single year for the sin of selling Joseph into slavery because, like David, we know that the cognitive distance that allows us to hurt others in order to make ourselves more comfortable, so long as the real harm is just out of sight, has not gone anywhere. The point is not to make us feel guilty about our choices. Joseph ultimately forgave his brothers; if his dialogue is to be believed, he did not even truly blame them, and yet the midrash tells us that each year since the first Yom Kippur in history, a piece of our atonement has been for Joseph. May this year be one where we close the gap of mental distance between ourselves and our siblings. May this be a Yom Kippur when those whose suffering we find reasons to ignore are close to our hearts. And may next Yom Kippur be a year we have just a little less to atone for.

May we all be inscribed and sealed for a year of life, goodness, and justice.

Rabbi Jonah Winer (he/him) is T’ruah’s director of learning. He was born and raised in Toronto and, after earning a BA in Religious Studies at McGill University, was ordained by Yeshivat Chovevei Torah in New York. While there, he worked as a Rabbinic Intern at NYU’s Bronfman Center and the Kehillah of Riverdale. After ordination, he spent three years working at Hillels, most recently as Senior Jewish Educator and Orthodox Rabbi at Brown RISD Hillel.

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