Sunday, September 24, 2023

The Gateway To Repentance: Kol Nidrei.23

 The Gateway To Repentance

Sermon for Kol Nidre Eve

By Rabbi Boaz D. Heilman

September 24, 2023



On a day not long ago, the phone rings in the rabbi’s office. Rabbi Rabinowitz answers. “Hello?”

“Hello, is this Rabbi Rabinowitz?”

“It is.”

“This is the IRS. Can you help us?”

“I’ll try.”

“Do you know Sam Cohen?”

“I do.”

“Is he a member of your congregation?”

“He is.”

“Did he donate $10,000 to the synagogue building fund last year?”

“He will!”


Ahhh! Jewish humor! And what better topic—especially for Yom Kippur—than guilt, and Jewish guilt in particular!

Of course, by now most of you must know my views on so-called “Jewish” guilt—that there’s really no such beast. Guilt is innate in all humankind and therefore crosses all cultural, religious and other imaginary divides. “Jewish guilt” is a stereotype, an example of a prejudice that goes back thousands of years. Still, we like to laugh at things we can’t do much about, and in this context of time and place, the topic isn’t completely inappropriate…

Guilt is part of the psychology of every human being. Used—and misused—for centuries by individuals as well as institutions, guilt can serve both to unite people but also to suppress uniqueness and individuality. Used as a verb—“to guilt”—it can become a form of emotional abuse.

But guilt does also serve a legitimate purpose. It’s there as a red flag, to let us know that we have done something wrong, or else to warn us that we are getting too near the danger zone, that we are about to err in judgment or behavior. It’s meant to direct us to do the right thing—or, if possible, to fix the wrong that was already done.

While guilt has only become subject for study in the last hundred years or so, we’ve always known its burden, and have always tried to find a way of being released from it. 

Today we may seek therapy, but in the past there were other ways of being cleansed of guilt. Most religions prescribe confession and penance—sometimes even to an extreme degree. The Torah commands a series of actions: First, public acknowledgment and a sincere apology, followed by restitution (often topped with a 20% fine); and finally a sacrifice meant to symbolically rid our souls of any residual feelings of guilt. Once these steps were taken, the individual was considered pardoned and absolved, their wrongdoing erased, never to be mentioned again.

There were also times for collective penance. When facing peril and danger, a king, prophet or rabbi (and sometimes a queen, too: think Queen Esther) could call for a period of atonement, a time in which a community would fast, pray and abstain from ostentatious behavior. 

One day in the year, however, was etched in stone, forever known as THE Day of Atonement: Yom Kippur. A day of personal as well as communal repentance, the rituals of Yom Kippur consisted not only of prayer and fasting, but also of a great number of sacrifices, including the famous scapegoat on whose shoulders all our sins were symbolically placed and which was then cast out into the wilderness. One of the most stirring moments of the day came when the High Priest entered the Holy of Holies—the only day he was allowed to do that—to encounter God’s own Sacred Presence and plead for forgiveness for himself, his family, and finally his people. Upon coming out, he would proclaim the Sh’ma, pronouncing the unity of God and the uniqueness of the relationship between God and Israel. Only then was the ritual of atonement complete, and we could move on with our daily routines.

This method may have worked in ancient days, but once the Temple was destroyed, everything changed. Without the ability to offer sacrifices, our relationship with God became an existential problem, and it became the ancient Rabbis’ most important task to re-define the Covenant between God and Israel in new and meaningful ways. 

The Midrash tells the story of Rabban (“Our Rabbi”) Yohanan ben Zakkai—who almost singlehandedly founded post-Temple, rabbinic Judaism—and one of his disciples, Rabbi Yehoshua ben Hananiah. One day the two were walking by the ruins of the Holy Temple in Jerusalem. Rabbi Yehoshua started weeping and tore his garments in mourning. “Woe to us,” he called out in his grief, “for this—the place where all of Israel’s sins were forgiven—is now destroyed!” Rabbi Yohanan said to him: “My son, do not be distressed, for we have a form of atonement just like it. And what is it? Acts of kindness, as it says (Ps. 89:3), ‘For I desire kindness, not a well-being offering’” (Avot d’Rabbi Natan 4:5).

Deeds of loving kindness go a long way towards bettering the world, but guilt is hard to expunge. A whole new set of rituals had to be put in place. New prayers replaced old sacrifices—including one so moving and significant that this evening’s entire service is known by its title: Kol Nidrei.

The date when this famous prayer was composed is unknown, but it is known to have been in wide use already in the sixth century CE.

Kol Nidrei has a long history of controversy. Common belief has it that the prayer was composed during a period of especially harsh persecution, when Jews were forced to choose between converting or being put to the sword. At that time, the text served to undo those vows made under duress and to reaffirm Jewish identity. In the eyes of the nations, however, this practice led to a general mistrust of Jews. As a result there were times and places when Kol Nidrei was altered or even completely removed from the service. 

Today however, no Yom Kippur is even thinkable without Kol Nidrei and its ancient and haunting melody.

But what is it about this prayer that makes it so powerful? And how has it come to symbolize the entire process of atonement? Its words do not speak of sins. No mention is made of sacrifice or contrition; nor does it even attempt to address God or beg forgiveness for our wrongdoings. 

But in having us declare all our vows null and void, Kol Nidrei frees us to examine what really matters to us. Repentance isn’t true unless it is freely made, not forced on us.

By the light of Kol Nidrei, we examine those values, ethics and morals that we hold up as highest and most sacred. Kol Nidrei doesn’t free us of our obligations, but its spiritual and psychological effect is such that it enables us to start again with a clean slate. Kol Nidrei opens for us the doorway to true repentance.


The purpose of Yom Kippur was always to give us a fresh start, an opportunity to turn a new leaf on life, to look forward toward the New Year with hope, not burdened with the stifling effect of guilt. This sacred day does not automatically absolve us of our guilt. The choice to atone, to realign ourselves with God’s purpose and reaffirm the Covenant, is ours to make. The lesson of Kol Nidrei is that as we renew our vows and make new promises, we pledge not necessarily to be perfect, but rather to be the best that we can be at any given time. And that’s why this prayer appears at the beginning of our service. It’s the gateway through which we, like the High Priest of olden days, take our tentative steps into the Holy of Holies, to face God and ourselves, to measure our accomplishments as well as our failures, and to begin again, with a clean heart.

May our prayers tonight and tomorrow serve the purpose for which they were created. May our atonement be acceptable before God, and may we be strengthened by this day to live by our highest ideals. 

L’shana tova tikatevu v’teichatemu—may we all be inscribed and sealed in the Book of Life for a year of love, happiness, health and peace, amen. 



© 2023 by Boaz D. Heilman


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