Jewish & Black: Wrestling with Identity and Purpose

Seeking Belonging in a World That Sees Differences

Introduction

It’s been a while since I’ve last written. For those who have followed my journey, you may have noticed my absence. The truth is, I needed time—to process, reflect, and wrestle with questions I haven’t yet answered. Writing is deeply personal for me. It’s not just about putting words on a page; it’s about owning my story, confronting my doubts, and giving voice to emotions I sometimes struggle to articulate.

Over the past few months, I have felt unmotivated, mentally and emotionally drained, and uncertain about my place in the world. But if there’s one thing I’ve learned, it’s that my story isn’t finished. And so, I begin again.

A Vulnerable Confession

One of the greatest compliments I receive in my public speaking and writing is that I am authentic. Authenticity is not just a trait—it’s something I strive for in everything I do. So, in that spirit, I begin this post with a vulnerable confession:

I have been feeling mentally and emotionally exhausted.

While I’ve already written several pieces for my blog, I am a perfectionist. The process of editing—selecting just the right words and choosing photos that convey my emotions and memories—is both time-consuming and draining. Just the editing alone takes countless hours. And the way I’ve been feeling lately, I haven’t had the energy or motivation to push through.

Honestly, a lot has fallen through the cracks. And yet, as shluchim (emissaries) of the Rebbe, we know his mission does not fail. Despite my shortcomings and faltering energy, his objectives continue to be fulfilled. My dear wife, Dalia, has been more motivated than ever—introducing new programs and inspiring students to engage in our events.

And as for me? Sometimes it feels like I’m just going through the motions. Others are doing the heavy lifting, and I feel like I’m just showing up. Even doing what I love—teaching, leading students in prayer, and welcoming them to our Shabbos table—has required extra effort. And somehow, despite everything, Hashem continues to provide for our needs.

Teaching Torah: Sometimes an act of inspiration, sometimes an act of perseverance. Either way, the learning continues.

The Weight of It All

In the meantime, my stagnation continues. What’s wrong with me? Why have I lost some of my drive? Maybe it’s a midlife funk. Perhaps I need to strengthen my connection to Chassidus, to deepen my spiritual bond with the Rebbe’s teachings. Perhaps it’s both.

This past Shabbos, sitting with my parents and daughters, gave me space to reflect. The weight of my responsibilities—35 hours a week in prison chaplaincy, my role as a campus shliach, father, and grandfather—has taken a toll. I have been under increasing pressure at the Department of Corrections, and it has been draining—I’ve spent countless hours litigating and advocating for religious accommodations for Jewish chaplains.

Meanwhile, the everyday pressures never go away: Shalom Bayis, health, finances, children. And then there’s the ever-present pain of the hostages in Gaza, which weighs heavily on my heart. It all adds up.

The recent passing of my longtime therapist, friend, and mentor, Dr. Michael Kahn, has also been incredibly difficult for me. He was one of the first people who helped me explore my biracial identity, who encouraged me to believe in myself. He helped me find my voice, and he always told me I had an important story to share.

Now, with him gone, doubt is creeping back in. I had taken for granted what he meant to me. And then, suddenly, he was gone—almost without a whisper.

Did the world feel his impact the way I did? Or was his faith in me misplaced? How will I ever know?

The sense of isolation is indescribable.

Seeking Belonging in Israel

As I continued to reflect, I also began to wonder: how deeply did my trip to Israel in December impact me? And what about the community lecture I gave shortly after?

In early December, I traveled to Israel as part of the MOED Leadership Mission, a project of the Jewish Federations of North America, with my friend and colleague, Rabbi Binyamin Murray. The trip gathered proud Jewish leaders of color—individuals who celebrate their ethnicity, embrace their skin color, and navigate the racial complexities of their identity.

I wanted to be there. I needed to be there. I intentionally stepped out of my comfort zone, hoping to bond with people who understood my experience in ways that others never could.

Side by Side with My Daughter in Israel—A Trip of Meaning, Reflection, and Bonding.

Traveling with my daughter, Shterni, was by far the most meaningful part of the trip. The time I was also able to spend with my son, Yehuda, and daughter, Mini, was precious, adding layers of depth to the experience. And there were moments I especially cherished—meeting with leaders in the Ethiopian Jewish community and getting to know members of Shachar, a small but proud Black Jewish community in Israel.

But my last day of the trip left me grappling with unexpected questions.

A fellow participant told me I couldn’t truly understand their struggles because my skin wasn’t dark enough. That only someone with very dark skin could really relate. Some in the group leaned into a form of racial essentialism, preaching the superiority of Black identity.

This didn’t resonate with me. I believe all people should be equal. But being told—again—that I wasn’t “Black enough”? It hit me hard. It reminded me of what I’ve faced my entire life—always navigating between two worlds, never quite fitting in.

I had come on this trip hoping to find a group that understood my plight, that could help me be proud of the complexities of my racial identity. But by the end, I wasn’t sure if I truly fit in. I was still searching.

There were many warm, kind people on the trip, but it left me wondering: where do I belong?

Learning from the Beautiful Souls of Ethiopia’s Jewish Community in Israel.

Pushed Back by My Own Community

And then, when I returned from Israel, that feeling was reinforced by Chabad colleagues.

I was invited to speak for a small community. The attendees were warm and engaged, and I could feel how deeply my words resonated. Yet, as I was introduced, it became clear that my story wasn’t familiar to everyone in the room.

After the talk, the local rabbi privately pushed back.

I get that you say it as part of your shpiel to engage the audience,” he said, “but do you really believe ‘I am proud to be Black’ is an important part of your identity?

He didn’t understand why I felt the need to express pride in being Black. Shouldn’t it be enough to say, ‘I am a Jew and a Chossid’?

He also questioned my childhood experiences—wondering if the kids who called me shvartze hotdog truly meant to put me down or if it was just harmless teasing.

Then, he brought up crime statistics and stereotypes, justifying why children might be uncomfortable around Black individuals.

I sensed his unease. He seemed uncomfortable that I had shared some of the racial ignorance present in the frum (religious) world with his community.

I left unsettled, doubtful that my message was wanted, questioning whether I had truly made any impact.

Conversations that matter—reflecting on identity, heritage, and belonging with those who understand the complexities of our journeys.

A Challenge to My Identity

Then came a series of small moments—seemingly insignificant, but together, they chipped away at me.

At a birthday party for Rabbi Gopin, the head Chabad emissary in Greater Hartford, I was asked to share about my Israel trip.

He listened and then emphasized that the Rebbe didn’t believe in “diversity” because he embraced all Jews as one. No distinctions. He recalled growing up in Kfar Chabad in the 1950s and ’60s, when the yeshiva printed on its stationery:

For the Immigrants of Yemen and Russia.

It was a time when Sephardic and Mizrachi Jews struggled for acceptance in mainstream Ashkenazi yeshivas. The Rebbe saw no differences. He welcomed every Jew equally from day one.

And I agree. That is why I love the Rebbe so much.

But as I said to my mother this past Shabbos:

I’m not sure what I stand for anymore.

Where do I fit in? What is my mission?

I shouldn’t feel shame when I look in the mirror. I want to take pride in my Black identity. I want to be able to say with confidence, I am Black.

But am I supposed to? Should it matter?

The rabbi questioned it. Two others, within days, questioned my embracing Black pride. Rabbi Gopin questioned it—using an argument I deeply believe in, one rooted in the Rebbe’s vision:

That we are all equal.

It shouldn’t matter. But it does—for everyone except the Rebbe.

Children as Catalysts for Growth

Chassidic teachings emphasize that children are not just students but teachers in their own right. They challenge us, inspire us, and draw out strength we didn’t know we had.

The Lubavitcher Rebbe often spoke about the profound impact children have on their parents’ spiritual growth, teaching that through nurturing and educating our children, we too are elevated. This isn’t just a theoretical idea—it’s a truth woven into our history.

Through Their Eyes: Learning, Growing, and Finding Strength in the Next Generation.

During Purim, when the Jewish people faced annihilation, Mordechai didn’t appeal to political figures or form alliances—he turned to the children.

He gathered 22,000 Jewish children, teaching them Torah and strengthening their faith. Their prayers, voices, and commitment became the catalyst for the Jewish people’s salvation.

The Rebbe once wrote:

No matter what one’s station in life is, or how important one’s activities seem to be, one must, first and foremost, dedicate at least some part of his time and efforts to the most important of all causes—saving our young generation. By implanting in them devotion to all that has been holy to us since our ancestors received the Torah at Mount Sinai, we ensure our future.
(Lubavitcher Rebbe, Letter, 7 Adar 5712 / 1952)

The Rebbe continued:

On the day when Jewish children are imbued with this spirit, and are ready to exclaim, ‘We remain with our Torah, for life or death’—on that very day, all Hamans will be defeated, and all Jews will have light, gladness, joy, and respect.
(Lubavitcher Rebbe, Purim Message)

As shluchim at the University of Hartford, this is the very vision we have dedicated our lives to—ensuring that every Jewish student is connected to their heritage.

The students and alumni who have become part of our extended family over nearly 25 years mean the world to me.

While I strive for Mordechai’s unshakable faith, I know this—my children have saved me more times than I can count.

They have kept me grounded when I felt lost, pulled me back when I drifted, and reminded me of my own strength when I had forgotten it.

I look at them, and I see the very reasons I cannot give up.

Conclusion: The Strength of My Children

Rabbi Tarfon teaches in Pirkei Avot:

It is not your duty to finish the work, but neither are you free to neglect it.
(Pirkei Avot 2:16)

I do not have all the answers. I do not always know where I fit in.

But I know this—my story is not over. And I cannot walk away from it.

Through all the questions, the doubt, and the exhaustion, one thing remains constant—my children are my strength.

They see in me a resilience that I sometimes forget I have. Their unwavering faith in me, their fierce loyalty, and their belief in the power of our family’s story sustain me when I feel depleted.

This past Shabbos, my eldest daughter, Lakey, reminded me of that when she asked:

Totty, people are waiting for your next blog post. When are you going to write again?

So here I am.

And as I return to writing, I turn my focus back to where this journey began—my children.

In my next post, I will share the experiences that shaped them, the challenges they faced, and the battles we fought as a family.

Because while I have spent my life searching for belonging, my greatest responsibility has always been to ensure that my children never have to question theirs.

Presenting President Isaac Herzog with Make Peace, a vision rooted in the Lubavitcher Rebbe’s timeless wisdom. The search for belonging continues, but one truth remains—our voices must be heard.