A Kippah in My Pocket, Light in My Heart: Personal Memories of Rabbi Sacks z”l

Journeys Around the World, Journeys of the Heart 

Thanks to the kosher vacations and Passover programs my father organized, I had the incredible privilege of working alongside him while traveling with Rabbi Sacks and his wife, Lady Elaine, to some truly magical destinations: the snowy landscapes of Lapland, the vibrant streets of Brazil, the lively culture of Argentina, the charm of Santiago, and countless other special places. Working so closely with my father and sharing these extraordinary experiences was a profound gift—one that I treasure deeply to this day. Each destination had its own wonder, but it was the wisdom, humor, and warmth of Rabbi Sacks that turned these journeys into something unforgettable.

Organizing these trips was no walk in the park. Coordinating kosher meals, keeping everyone on schedule, and making sure everything ran smoothly was a constant juggling act. Most of the guests were kind and appreciative, but there were always a few whose complaints could sour the mood. It wasn’t easy, especially after a long, exhausting day.

But just when spirits were low, Rabbi Sacks and Lady Elaine would step in. Rabbi Sacks had a knack for lightening the mood with a clever joke, a meaningful verse, or just the right words of encouragement. Lady Elaine, with her ever-polite smile, would walk by and softly whisper, “Everything is lovely, Yehuda.” Rabbi Sacks would say to my father, “Zvi, what a day—well done, brilliant.” It might seem like a small gesture, but those moments carried so much weight. They lifted us up and gave us the energy to end the day with a smile.

Walking Into Thought – During these trips, I had a daily and nightly ritual: a quiet walk with a small flask of whiskey and a cigarette, letting the day settle in my mind, or sitting at the back of the bus by myself before a very long ride. Rabbi Sacks also valued his alone time, and now and then, we’d cross paths during these walks around the hotel or on the bus.

At first, these encounters were short—a polite nod, a smile, and he’d carry on. But as time went on, those brief moments turned into conversations, and eventually into something much deeper. We talked about soccer (mostly about the wonderful days of Arsenal), about questions of faith and loneliness, and even about my decision to take off my kippah. One night, he paused and said to me:“Yehuda, don’t overthink it—it will give you a headache. The kippah doesn’t have to be on your head. It needs to be in your head. Just make sure it’s always close to you.”

Since that moment, my kippah has always been in my pocket. I learned a strong lesson: ideas are more important than symbols. What we think and how we behave are more important than what we wear—something that, unfortunately, is often the opposite in today’s Israeli society.

I learned a strong lesson: ideas are more important than symbols. What we think and how we behave are more important than what we wear—something that, unfortunately, is often the opposite in today’s Israeli society.

Between Faith and the IDF – Rabbi Sacks believed with all his heart that the Israeli military wasn’t just a national necessity—it was sacred. To him, soldiers weren’t just defenders of Israel; they were heroes. He saw the army as one of the few places where secular and religious Israelis truly come together, working side by side for a shared purpose.

Whenever we talked, he’d ask about my military service and encourage me to speak openly. He listened intently as I shared stories of challenges and the heavy toll combat can leave behind. What struck me was his genuine concern. On one of the hikes, we met a few Israeli guys who had just finished their army service and were traveling in South America. They recognized Rabbi Sacks and asked him for a short dvar torah (talk or essay based on the weekly Torah portion) before continuing their journey. Rabbi Sacks was so deeply moved by these three young men. He turned to one of the group members afterward and said, “These guys are the best of the best the Jewish people will ever have. Brave and proud, humble and curious.”

The Israeli guys we met in South America

Read, Question, and Don’t Be Afraid– If there was one thing Rabbi Sacks consistently preached to me, it was the importance of learning. His mantra: “Always read. It’s never enough.” On Shabbat morning, he once told us, “Being a good Jew is being a lifelong learner—someone unafraid to question, doubt, and grow.”

After losing my job, I fell into a state of silence and withdrawal. It was during one of our trips that he suggested something radical: leaving Jerusalem, the city I loved, and moving to Tel Aviv—a place I didn’t yet feel connected to. “Take the leap,” he urged, “start fresh.” His words gave me the courage to take that step. In doing so, I found a new chapter of growth, light, and renewal. I’ve been living in Tel Aviv for seven years now. It’s definitely my home, and that’s thanks to him.

A Gentleman With Style – Rabbi Sacks exuded a rare blend of European sophistication and quiet confidence. Everything about him—the way he walked, spoke, dressed—carried an effortless refinement and charisma. He had this ability to hold a room, ignite minds, and touch hearts with every word. When he spoke, it wasn’t just profound—it was electric. You could feel, without a doubt, that you were in the presence of someone truly extraordinary.

Sometimes, one of the group members would ask him a question—about how to pray on the bus, whether a certain vegetable was kosher, or whether a whiskey could be drunk. With a small smile, he would reply, “I don’t know, but you could check for yourself in the book in your hand.” I loved it. Everyone on the bus loved it.

You’ll see, Yehuda,” he once said, “pain and failures will teach you the most important lessons in life. I have no doubt that one day you will bring light to someone and do good for the Jewish people. But first, you have to taste the darkness before stepping into the light.

A Personal Farewell 

For me, Rabbi Sacks wasn’t just a leader in the Jewish world—he was a personal guide who believed in me when others gave up. He had a way of finding light even in the darkest moments, reminding me, as Leonard Cohen so perfectly put it: “There is a crack in everything; that’s where the light gets in.” “You’ll see, Yehuda,” he once said, “pain and failures will teach you the most important lessons in life. I have no doubt that one day you will bring light to someone and do good for the Jewish people. But first, you have to taste the darkness before stepping into the light.”

What I’ll hold onto most from those wonderful trips are the simple moments: seeing how my father treats his guests and every person he meets (guests and waiters). the late-night conversations and quiet walks with rabbi Sacks, singing with him and my father on Friday nights and just talking to him, with a cigarette in my hand, and a kippah in my pocket.

Goodbye, Rabbi. Thanks for believing in me. You’ll always be in my heart.

Ushuaia: Penguin Island