Sermon for Yom Kippur 5786

Many of you know that I have Jamaican heritage.  My paternal grandmother, Olive Levy Rosenfield, who passed away in 2010, was born and raised in Kingston, Jamaica.  She proudly claimed that her ancestors came to Jamaica with Christopher Columbus when they were fleeing the Spanish Inquisition in 1492. While my mother, our family’s genealogist, hasn’t traced our ancestry quite that far back, she has documented at least eight generations of the Levy family.

I had the blessing of traveling to Jamaica twice to explore this heritage — once in 2002 with my grandmother, and again in 2006 for the 350th anniversary celebration of Jamaica’s small but enduring Jewish community.

I’ve always taken pride in my Jamaican Jewish roots, especially because they are so intertwined with my grandmother, with whom I was so close. Though she left Jamaica to marry my grandfather in 1942, her accent never abated. She filled my life with intense color and emotion. From her I inherited a love of singing, dancing, and painting. Everything reminded her of a song. She would sing Jamaican ditties to me—often with dirty lyrics! For holidays and family gatherings, she made flavorful goat curry and oxtail stew, in stark contrast to the bagels and kugel served in our Ashkenazi New York community. Because of her, I grew into a rabbi who was deeply interested in the diverse heritage, history, and culture of Jewish people around the world, recognizing the diversity of the Jewish experience. 

That’s why we started Sharing Our Stories at Kol Emet. Over the years, members have shared their stories of having Scottish-Jewish and Cuban-Jewish heritage, as well as stories of conversion, queer-Jewish stories, and journeys through Orthodoxy, Reconstructionism, even atheism. It’s been a beautiful way to get to know one another, to learn from one another, and to honor the diverse backgrounds and beliefs that make up our community.

But I haven’t shared my own story, not really.  And what I’ve told you just now about my Jamaican Jewish heritage is the tip of the iceberg.  For years I have been immersed in my family genealogy and history, and it’s truly fascinating.  But it’s also complicated, and painful.  History, as we know, has layers. And when you dig deep enough, you uncover truths that are harder to face. 

You may know that, for centuries, Jamaica was a major hub of the transatlantic slave trade. I had realized that some of my ancestors almost certainly were slave owners — after all, my great-great-grandparents had a plantation. I’d been to its site and chronicled all the names in the family cemetery. 

I also knew that there was an earlier time in Jamaican history, during Spanish rule, when Jews were not allowed to be land owners.  So, they became traders and merchants in the ports.  And what did they trade?  My mother, our family’s amateur generologist, discovered that one ancestor in particular, Alexandre Lindo, owned and was the captain of at least two ships, ships that carried kidnapped Africans through the harrowing Middle Passage between Africa and Jamaica.  He was also known for his brutal tactics in selling masses of enslaved people “efficiently” and thus is considered by historians as the most notorious Jewish slave trader of the 18th century.

When I learned this, I felt shame—a deep, unsettling shame. It wasn’t anything I personally did; I just didn’t know how to reckon with this terrible piece of my history that I was now aware of. I felt that I could no longer talk about my Jamaican heritage with pride.  So, I didn’t. I stayed silent. 

And that, as Brené Brown teaches, is exactly how shame thrives.  Brown, a researcher and storyteller, says that shame isn’t just about what we’ve done — it’s about who we believe we are.  I could certainly resonate with that.  

She defines shame as “the intensely painful feeling or experience of believing we are flawed and therefore unworthy of love and belonging.” (Brené Brown, “The Power of Vulnerability” TED Talk, 2010)  We don’t all experience shame the same way or for the same reasons, but it’s an undeniably powerful feeling that is hard to shake.  I think about people who have survived violence, extreme poverty, family separation, grave illness, and more – people who haven’t done anything wrong but who often feel shame about what they went through and still carry the stigma of their experience.  Why is that?  

Brown also teaches that shame thrives on three things: secrecy, silence, and judgment.  And that the way to dismantle shame is through vulnerability— telling our story to those we trust, people who have earned the right to hear it. (Brown, “Daring Greatly,” 2012)  Sometimes society shuts down the voices of those who speak uncomfortable truths, those who survived.  It tells us there is no acceptable place to tell our story.  And sometimes it is ourselves that shuts down the voices inside us that whisper our shame.  

So here we are, on the most sacred day of the year, the day of moral reckoning, a day for fasting, reflection, and forgiveness.  We confess our shame and regret and we lean into God’s infinite compassion.  This is an opportunity to examine our shame and hold it up to the light.

The first use of the word “shame,” or boosha, in the Torah is in the story of Adam and Eve, and notably, it appears in the negative form:

וַיִּהְיוּ שְׁנֵיהֶם עֲרוּמִּים, הָאָדָם וְאִשְׁתּוֹ–וְלֹא יִתְבֹּשָׁשׁוּ

“And the two of them were naked, the man and his wife, and they were not ashamed.” (Genesis 2:25)

Adam and Eve did not feel shame—because they had not yet become aware of good and evil.  However, after they eat from the Tree of Knowledge, the text says, “Then the eyes of both of them were opened, and they realized they were naked.” (Genesis 3:7) So, once they gained knowledge, they also gained the capacity for shame.  

The text says when they beheld their nakedness, they wanted to cover themselves up.  Perhaps it was not so much their physical nakedness they wanted to conceal, but what it represented: their vulnerability, their imperfection, their mortality. In their new consciousness, they saw what was lacking and felt exposed. They now could see themselves more clearly – humans, possessing both an evil inclination and a good inclination, imperfect, flawed. 

As humans, we are not created to be perfect. We are created with both yetzer ha-tov (the good inclination) and yetzer ha-ra (the evil inclination). We are meant to struggle. And we are born into a world that is already broken—a world shaped by sins that predate us: racism, antisemitism, slavery, climate destruction, misogyny, and war.

I was raised in a liberal Jewish community that championed the ideals of  Israel and Zionism. But Israel was much more than an ideal to me. I lived in Israel for a year at age 12 and became a Bat Mitzvah there, at a progressive congregation in Jerusalem. I returned in college, to study there for a semester, and then again before starting rabbinical school, spending a summer at Hebrew University.

It was the year 2000. Every day, I rode a bus through East Jerusalem filled with Jews in kippot, Arab men in keffiyehs, and young soldiers in army uniforms and guns slung across their backs. There was an ease and a hope on those bus rides I honestly took for granted. But just three weeks after I left Ariel Sharon ascended the Temple Mount, and the Second Intifada erupted, seemingly out of nowhere. 

How could this have happened – after the relative peace I had witnessed??  That’s when I started learning the Palestinian narrative—their experience of displacement, their immense losses, and their devastation. What I thought I knew was suddenly incomplete. 

And there it was again: shame. Israel was part of my identity, much like Jamaica. But how could I hold my deep connection to Israel alongside the pain and injustice I now saw? Thankfully, I was blessed to be in rabbinical school, in a place that honors questions, encourages deep reflection, and honors complexity, of holding multiple truths at once.

But that was 25 years ago.  As we know, Israel is a different story, in some ways, than Jamaica, in that there are red lines in the American Jewish community around any criticism of Israel. There is a silencing that leads to shame, and that shame creates distance and judgment—within our community and within ourselves. This is not new.

But now, as the war in Gaza nears its second full year, we find ourselves in an impossible place, heartbroken for those we love in Israel and for all we lost on October 7, 2023, and horrified by the immensity of the suffering we are seeing in Gaza, with no end to war in sight.  In addition, the escalation of anti-Semitism from the left and right is truly alarming. 

Yossi Klein haLevi, the noted Israeli author and thinker, describes our quandary: “To be an ambivalent Jew today is not to be uncertain so much as torn between conflicting certainties.” But, in this toxic atmosphere, if we dare critique or question or doubt, we might “risk inadvertently reinforcing the campaign of hatred and lies” against us. (Yossi Klein haLevi, Our Season of Reckoning: Israel’s Moral Crossroads in Gaza, The Times of Israel blogs, Sept. 7, 2025) 

There is no space for us to make moral sense of any of this, no space for us to share our fears, doubts, questions, no space to delve into nuance or complexity. At times it feels that to express sympathy for one side is to deny the humanity of the other. 

But this isn’t a zero sum game.  We know the Israeli-Palestinian conflict is decades old, and we know there are multiple truths and multiple narratives that often contradict one another. But it is so hard to simply hold the multiple truths of this terrible conflict in our minds and hearts at once. 

The Tree of Knowledge wasn’t just about sin—it was about complexity. Adam and Eve ate from the tree of knowledge, that is, the tree of awareness and consciousness, and realized there were multiple truths that conflicted with one another. And that, I believe, was the seed of their shame.

Shame often arises when our brains perceive a contradiction between our values and our actions—or between our values and our identity. Think about someone who steals a necklace. If they believe stealing is wrong and see themselves as an honest person, the act of stealing creates dissonance. That dissonance produces shame.

Thus, shame, in itself, isn’t necessarily a bad thing. In fact, in his comment on the story of Adam and Eve, the medieval commentator Rashi teaches that shame is the first sign of moral consciousness. It can be a powerful indicator of when one has transgressed upon one’s morals and beliefs.  

Shame, then, is something to listen to. It’s the beginning of teshuvah— of return. We can’t undo the past. Some things cannot be restored. But shame reminds us where the cracks are. 

There is a movie that every kid 10 and older of every gender and the grown ups who live with are watching called KPOP Demon Hunters.  I highly recommend it.  It’s Korean, with super catchy music.  A girl named Rumi is a singer in a popular band and is adored onstage, but she has a secret. Hidden under her sleeves are markings that reveal that her father was a demon.  She fears that if people knew, they wouldn’t love or admire her anymore. The movie portrays a culture of perfection, of wearing masks and never revealing your flaws.  The demons prey on this facade, whispering “You are too much. You are not enough. You will never belong.”  Her fear echoes so many of our fears today: If so-and-so knew this about me, would they still respect me? Would I still belong?” Ultimately she realized that the only way to overpower the demons is to reveal her scars and embrace who she truly  is.  

It sounds so easy, right?  But the culture of perfection is so hard to overpower in one’s psyche.  The patterns that Rumi is ashamed of are the result of factors she couldn’t control in her childhood that made her feel like she needed to hide forever. Her mother figure tells she needs to hide her scars forever.

But there is no such thing as perfect.  Everything is messy, and ugly under the surface.  And we see that pushing away shame actually feeds it.  Denying shame tells us there is only one valid truth, that we need to pick a side. Denying shame tells us that if we empathize with the suffering of another people, that we betray our own.  Denying shame is why people are removing books from school libraries and exhibits in museums that portray white people in a critical light, as slave owners and violent defenders of segregation. In my case, denying shame also means denying my pride and connection to my own heritage. 

Shame keeps us morally aware and humble. It is not, as some might claim, a form of self-hatred.  Rather, it is a spiritual tool, and that according to our sages, can lead us to wisdom and keep us from repeating our mistakes. 

Our tradition is full of figures who felt deep shame and used it as a catalyst for change. Take King David. After his sin with Batsheva, he is confronted by the prophet Nathan and immediately confesses, “Chatati l’Adonai – I have sinned before God” (2 Samuel 12:13). Even though God forgives him, David still feels the lingering weight of his shame.  The shame remains—not as punishment, but as memory. As a moral guidepost.

So the question becomes: What do we do with our shame? How do we let it guide us without letting it define us? Rabbi Abraham Joshua Heschel answers this beautifully in his book God in Search of Man. He writes:

“Should we then despair because of our being unable to retain perfect purity? We should, if perfection were our goal… All we can do is to try to wring our hearts clean in contrition. Contrition begins with a feeling of shame at our being incapable of disentanglement from the self. To be contrite at our failures is holier than to be complacent in perfection.” (Heschel, God in Search of Man, 1955)

This is the spiritual invitation of Yom Kippur. We beat our chests and confess Ashamnu — “We are guilty.” But right before that, we sing Ki Anu Amecha, reminding ourselves: We are Your people. You are our God. We are Your children. You are our Parent. We confess our failures not because we are worthless, but because we are beloved. Because we know we can be more.

Our morning liturgy offers a quiet but profound prayer as we go into the Shema:  “V’lo neivosh, v’lo nikalem, v’lo nikashel l’olam va’ed. — May we never be stuck in shame, embarrassment, humiliation.”

In that prayer, we ask God to enlighten our eyes with Torah, to keep us connected to our purpose, to lead us proudly back home–and from shame.  Why? Because shame isolates you from Torah, God, and home. The deepest Jewish worry is alienation from one another because of shame.  

Rumi sings,
“The worst of what I came from, patterns I’m ashamed of
Things that even I don’t understand
I broke into a million pieces, and I can’t go back
But now I’m seeing all the beauty in the broken glass
The scars are part of me, darkness and harmony
My voice without the lies, this is what it sounds like”

We live in a world that punishes vulnerability, that shames difference, and that tells us to hide our complexity. But Yom Kippur invites us to do the opposite. This day calls us to step forward — not perfect, but honest. Not proud, but open. Not blameless, but beloved. Not to erase the difficult parts of our story, but to face them. To carry all the parts of ourselves with integrity.

We are not meant to carry shame as a permanent identity. We are meant to transform it.  Find ways to share your story.  Listen compassionately when others entrust you with their questions and doubts.  Commit to good deeds that restore your sense of pride and dignity, that can serve as a positive example to others.  

The Christian author Ann Voskamp writes: “Shame dies when our stories are told in safe places.” But how many safe places are left?  When there is no safe space to speak from a place of vulnerability, confusion, or shame, the silence becomes distance, and the distance becomes disconnection— not only from community, but from Judaism itself.

That is why we must continue creating space at Kol Emet for people to share where we are really coming from. Our backgrounds, our struggles, our beliefs—even when they are complex or messy. Especially then.

Sometimes the shame we carry isn’t even about things we’ve done—it’s about things done by our ancestors, our people, or the communities we love.  In those cases, shame is a kind of mourning: a disappointment in those we identify with.  In my case, the shame I felt around my Jamaican ancestry pushed me to ask deeper questions about my responsibility to share this history and make what reparations I could.  

And so I ask you this Yom Kippur: Where is shame showing up in your life? Is it tied to something you’ve done? Something your people have done? Something you carry that isn’t even yours, but feels like yours? And more importantly — what would it look like to face that shame, not with denial, but with curiosity? With compassion? With a yearning to return to God, to your purpose, to your best self?  

We feel shame because we care. Because we are proud. Because we hold ourselves to a certain moral standard.  Because we know we’re bound together.

That is what we bring to this day. Our Torah reading from Leviticus 16 tells us of the High Priest, who offers atonement not only for himself, but for his household and for all the people of Israel. Even our ancestors knew that sin—and shame—are collective, as I spoke about last night. But so is healing.

Yom Kippur teaches us that who we are is never beyond repair. 

As Deuteronomy 10:16 says: “Umaltem et orlat l’vavchem – Cut away the thickening around your hearts.”  

Let your heart feel. 

Let your heart break.  

Let your heart be known. 

And let your heart guide you home.

Gmar chatima tovah – May you be inscribed for a good new year.