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YK 5786 | Rabbi David Wolkenfeld

10/03/2025 01:31:25 PM

Oct3

Praying with Sinners and Praying for Sinners

Many years ago my father in law shared a helpful mnemonic for remembering the six fast days of the Jewish calendar. They are, the black and the white, the man and the woman, and long and the short.

The “black” fast is Tisha b’Av when we cover the shul in black drapes and sit in the dark. The “white” fast is Yom Kippur because of how we are all dressed. The “man” refers to the Fast of Gedaliah and “the woman" refers to the Fast of Esther. The long and the short are the 17th of Tamuz and the 10th of Tevet. Or, in the Southern Hemisphere the tenth of Tevet and the 17th of Tamuz.

But in Talmudic times, in addition to the regular communal fast days that commemorate events of Jewish history, fasts were declared in communities in response to calamities. In Rambam’s formulation:

וּמִדִּבְרֵי סוֹפְרִים לְהִתְעַנּוֹת עַל כָּל צָרָה שֶׁתָּבוֹא עַל הַצִּבּוּר עַד שֶׁיְּרֻחֲמוּ מִן הַשָּׁמַיִם.

…by rabbinic ordinance, it is required to fast for any calamity that befalls the community, until mercy is granted to them from Heaven.

And the circumstances of which sort of calamities created an obligation to fast and the specific procedures for declaring the fast and the additional public prayers that took place on those fast days are the central subject of the Mishnaic and Talmudic tractate of Ta’anit. And in the midst of this vast and complex series of conversations and debates and discussions is a Talmudic passage, in the Yerusalmi, the so-called Jerusalem Talmud, that shocked me to my core when I stumbled upon it last summer.

We declare fast days, the Yerushalmi teaches, in response to droughts during all seven years of the shemitah cycle. In the seventh year, the shemitah year, when Jews are forbidden from engaging in most agricultural labor, we fast and pray on behalf of others. Who are those others?  Rabbi Zeira says that we declare a public fast during a shemitah year drought so that those Jews whom we suspect engage in forbidden agricultural activities during the shemitah year can be sustained by their farming.

Recall that the Torah imposes a number of significant prohibitions against agricultural labors in Eretz Yisrael during every seventh year, the shemitah year. And the rabbis formed a sort of religious elite who cared about observing these mitzvot even when many of their Jewish neighbors, let alone the many non Jewish neighbors, paid them no heed. Entire chapters and tractates of Mishnah and Talmud are occupied with the challenges of being a religious minority, even among Jews.

And yet, the Yerushalmi teaches that we fast and pray so that these Jewish sinners would be able to farm and gather their harvest and support themselves in a dignified - albeit forbidden - way during the shemitah year. 

The Yerushalmi’s call to pray for sinners reminded me of the beginning of Yom Kippur when we declare that, at least on this day, we will pray with sinners. 

עַל דַּֽעַת הַמָּקוֹם וְעַל דַּֽעַת הַקָּהָל. בִּישִׁיבָה שֶׁל מַֽעְלָה וּבִישִׁיבָה שֶׁל מַֽטָּה. אָֽנוּ מַתִּירִין לְהִתְפַּלֵּל עִם הָעֲבַרְיָנִים:

With the consent of the Almighty, and consent of this congregation, in a convening of the heavenly court, and a convening of the lower court, we hereby grant permission to pray with transgressors.

This opening passage can be traced to Rabbi Meir of Rothenberg, who was among the last great rabbis of Medieval Ashkenaz before the Black Death and the expulsions in the 14th century brought an end to its creative brilliance. 

There is also real ambiguity in the various commentaries about what is happening when these words are chanted. Has a beit din, a rabbinic court, been convened in shul such that three men need to stand in shul to make the declaration? Or, is the shaliach tzibbur, the prayer leader, making the declaration as our emissary on behalf of each of us who listen to his words? The common practice is confusing. On the one hand, two men stand alongside the shaliach tzibbur, forming an ad hoc beit din. On the other hand, the shaliach tzibbur makes the declaration alone.

And who are we praying with? The 17th century commentary to the Shulhan Arukh, Beir Heitiv, says that those who transgressed communal norms and ordinances who had been banned from communal participation are permitted to return to shul for Yom Kippur by means of this declaration. 

According to Rabbi Yoel Sirkis in his 16th century commentary to the Tur, known as the Bayit Hadish, or Bah, the declaration shouldn’t be taken to mean more than what it says. We allow the sinners to join us for Yom Kippur. But there is no full reconciliation. We have not forgotten what they did. But they are a part of our fast. 

Searching farther into the past, the Talmudic sage Rabbi Shimon Hasida says that any fast at which the sinners of Israel do not participate is not a fast:


כׇּל תַּעֲנִית שֶׁאֵין בָּהּ מִפּוֹשְׁעֵי יִשְׂרָאֵל אֵינָהּ תַּעֲנִית, שֶׁהֲרֵי חֶלְבְּנָה רֵיחָהּ רַע וּמְנָאָהּ הַכָּתוּב עִם סַמְמָנֵי קְטֹרֶת. אַבָּיֵי אָמַר: מֵהָכָא: ״וַאֲגֻדָּתוֹ עַל אֶרֶץ יְסָדָהּ״

After all Helbanah is a foul smelling substance but it was included in the incense that was burned in the Temple. 

Rabbenu Bachaya says that just as the helbanah was an indispensable ingredient in the incense mixture, the prayers of the righteous are not accepted without the prayers of the wicked alongside. They are indispensable to the teshuvah process. After all, as the Rabbi Hayim Dovid Azulai notes, who else will repent, who else is Yom Kippur for, if not for the wicked?

When we contemplate praying for sinners or when we pray with sinners a very unusual and very special dynamic is created. We have not collapsed the category of sin and transgression. We maintain that there are sinners who violate communal norms or violate the rules of the Torah. There are sinners and we want to be with them on Yom Kippur. There are sinners and we worry about how they will fare during a drought. 

Love and acceptance without relativism is so very rare but is so very necessary. 

I came of age during what might have been a lost golden age for Jewish pluralism. Educational institutions like the Bronfman Fellowships, Pardes, and Hillel exemplified a pluralistic ethos in which Conservative, Reform and Orthodox Jews studied Torah together and built Jewish community together. 

When Edah, the Modern Orthodox advocacy organization was founded in 1997 its vision statement spoke of “an Orthodox Jewish community within which we, as members, leaders, and institutions, reach out to and interact with Jews of all the movements…as an expression of the wholeness of, and in an effort to strengthen the entire Jewish people.”

When YCT Rabbinical School opened in 1999 its “core values document” called for “actively pursuing the positive and respectful interactions of all Jewish movements.”

In 2000, journalist Samuel Freedman published “Jew vs Jew” a book in which he warned of a looming schism that would divide North American Jewry between left and right and between Orthodox and non-Orthodox. But that schism never materialized in the way that he predicted. It has been suggested that the explosive growth of Orthodox outreach institutions and Chabad houses has served as a unifying force. There are more Orthodox outreach professionals in North America than there are Reform and Conservative rabbis combined. This means that there are thousands of Orthodox Jews whose livelihood depends on their ability to foster positive interactions with non-Orthodox Jews, and there are hundreds of thousands of non-Orthodox Jews whose mental image of Orthodoxy is the friendly Chabad rebbetzin rather than the scary and authoritarian rabbi their great-grandparents feared in the shtetl.

The schism did not come, but I fear it may be coming. Different opinions about Israel and Zionism,  and different ways of speaking about Israel and Zionism, and different forms of activism about Israel and Zionism have divided congregations and families and friendships in ways that religious differences rarely do. And this is understandable. The stakes are very high. The stakes could not be higher. The only thing, at this point, that unites the North American Jewish community is the belief that the other side of the divide is complicit in grave moral errors or worse. 

And everything we think about them, they think about us - and I leave each of you to decide who is “we” and who is “they” because every “we” is someone else’s “they.”

I have heard from fabrent Zionists who are confounded by their children and grandchildren’s politics. And I have heard from non Zionist Jews who are desperate for a community to observe Shabbat and to learn and daven where their worldview can be reflected as well.

It could be that the religious pluralism that flourished in the 90s was not the result of a sophisticated philosophical commitment, but was a function of being unthreatened and unfazed by how other Jews observe or do not observe mitzvot. We don’t extend that same embrace to those who oppose our politics on Israel because lives hang in the balance. 

But our ancestors thought that how Jews observe the shemitah year had life and death implications for all of us and they still prayed for their sustenance. Our ancestors had no trouble labeling some people as avaryanim - as sinners - and then publicly inviting them to sit alongside us on Yom Kippur. 

Not all choices are equally valid. Some choices are actually harmful. And lives really do hang in the balance of our activism. And whichever opinions you hold and whichever direction that activism takes, there are hundreds of thousands of Jews who think you made the wrong choice. Maybe we will be able to work out our differences and come to some agreement. Maybe if the war comes to an end, the salience of these differences and the heat of our disagreements will taper and that is one of the things I pray for when I pray for an end to the war.

But it could be that the fissures we now see will only grow over time.  I do not think it is tenable or desirable to paper over those differences with appeals to the pluralism of the 90s. At times, we can label people sinners based on their words and actions. But let’s at least pray for them. They too are our brothers and sisters, our parents and our children. And we should want the best for them.  

Maybe some synagogue communities will divide as Jews sort ourselves among those who see the big questions of Jewish life as we do, but at least on Yom Kippur, let’s make room for everyone to enter. 

And, everything that is true horizontally, among Jews alive today, is true vertically between generations, and it is true internally within ourselves. And Yizkor offers an opportunity to express that.

There is an odd phrase in the Vidu’i, the confession, that appears throughout the Yom Kippur liturgy. We say, again and again, “aval anachnu v’avoteinu chatanu” - we and our ancestors have sinned. Why do we need to confess on behalf of our ancestors? The Torah is clear that children are not punished for the sins of parents and parents are not punished for the sins of children. Why confess for our ancestors? 

Rav Soloveitchik answered, “because we have a covenant with God we may speak of a historical ethical memory and a historical continuity ... The individual is not guilty of sins perpetrated by past generations, but the group bears responsibility for the sins of the past.”

On Yom Kippur we confess on behalf of every Jewish generation. We experience atonement alongside every Jewish generation. We offer forgiveness for every Jewish generation.

At Yizkor, we invite our memories of deceased loved ones, parents and grandparents, husbands and wives, brothers, sisters, and children, into the room with us. The Righteous and the wicked are invited to shul. We engage with memories that are positive and with memories that are mixed. 

I had one Hasidic grandmother and one Communist grandmother. I am neither Hassidic nor a Communist, but I like to think that each of them could see something in me to be proud of, and I engage in an ongoing dialogue with each of their memories. At Yizkor on Yom Kippur, all of our memories of deceased family are invited into the shul with us. 

And we then have an opportunity to contemplate who we wish to be in the days to come in light of that encounter with their memories. 

Thu, October 23 2025 1 Cheshvan 5786