A Cup of Blessing

Though technically I grew up in Philadelphia, in many ways I was raised in New York. Growing up in the 70’s and 80’s with three sisters, one my twin, two older, and a younger brother who showed up only much later, my cultural exposure, though certainly more diverse than many Chassidic children, consisted primarily of ABBA, Eight-tracks of London School of Jewish song, and Shlomo Carlebach records. Sunday mornings were reserved for Barry Reismans radio show, which in retrospect, seemed more like a front, a thinly disguised attempt at promoting the limited but full extent of the then fledgling Jewish music scene, when in reality it was almost exclusively dedicated to promoting the two reigning syndicates of Jewish song, the Barry sisters and the brothers Zimm.

The Northeast public library became a second home for me, where just a short walk from my home an exciting world awaited, always a warm and safe place. Though my father is a Russian born Israeli, my mother is a Connecticut Yankee, who grew up listening to the Beatles, and knew intuitively, that I needed more literary diversity than the ever-present, obscenely thick — Sears catalogs that seemed to sprout seasonally from some hidden catalog plant in our bathroom.

My religious upbringing was more complex. Though centered around the regular rhythms of an observant Jewish home, we were Chassidim of the Lubavitcher Rebbe and we regularly crossed state lines, for routine late night mini pilgrimages to Brooklyn.

In retrospect my childhood bore a weird similarity to the whole era of Grateful Dead groupies and Phish heads, that shlepped their children all over the country for concerts. I have to believe that though we were worlds apart culturally, the goals were somewhat similar — satisfying a deep generational need for spiritual light. In truth though, there were actually many differences. Far more than I care to enumerate here. One of the biggest was that though we were constantly traveling, there was always only one destination, always one venue. The late night Chassidic Farbrengens, were always heady and intense, always “sold out,” and always held at the Rebbe’s humble “arena” in 770 Eastern Parkway.

Though we lived “out of town” my father was, and still is an “emissary”- a Shliach of the Rebbe, and as such was entitled to a “place” – an exalted privilege. Think courtside tickets to the Lakers Vs Celtics in game seven of the finals, except there was no dollar figure in the world for which we would ever give up our exalted spot, me fidgeting on my fathers lap, on a rickety splintery bench, front row seats, observing in awe how one of the greatest Jewish spiritual maestros of our time composed, and conducted a symphonic version of a global Jewish movement, one that has singlehandedly transformed the landscape of Jewish life in our times.kos she l bracha This “place” at the Farbrengen was always a symbol for me of a slow but certain carving out of my own “place” in this world.

In retrospect though I must have tortured my father with my inability to sit still there for long. Come to think of it I don’t think I’ve ever thanked him properly for that ultimate gift, he didn’t need to shlep me, but he did. I will call him today and say thank you, for giving me the gift that has miraculously kept on giving.

There is a new genre that has sprouted up in the world of Jewish literature based on people who grew up Chassidic and became disenchanted with it. I’m not sure why these memoirs are so popular. I suspect it might have something to do with an assuaging of Jewish guilt, and a collective “I told you so” that this lifestyle couldn’t possibly survive, an absolution of sorts, “our instincts to go the secular route were spot on.” and so on … or not.

Either way I’ve always fought that mentality, on the grounds that I was always taught the opposite, that being observant didn’t make me more Jewish, and that the majority of my less observant friends were no less Jewish than I was.

Still lets face it, stories like mine, consisting of a Jewish background and upbringing that continues to nourish and inspire me would never sell. Yet nonetheless I write. For myself, and for those of you that read. I won’t write a memoir, but I will tell you some stuff.

I will tell you how fortunate I feel, in the myriads of ways that my upbringing has given me so many opportunities to go back and drink from that well.

I will also level with you and confess that by no means has it been a simple journey.

My relationship with the Rebbe’s teachings has often been complicated for me. Whether as a child, struggling with my relatively open upbringing, and often feeling like an outsider as I grew older and left home to join the required Chabad Yeshiva system, or the trauma that I know I suffered, for years — after The Rebbe passed.

While many of my peers quickly tried to fill that void by substituting the real Rebbe with a video version, it was years before I was emotionally healthy enough to start watching the videos or downloading the audio clips. For me It has turned out better to face the reality of his passing, in a way that enables me to focus on keeping his essence, his vision, found only in his teachings, alive — but it took a while for me to get to where I am today. Fortunately I have always been passionate about the work I’m doing. Its never been an issue for me and I’ve always felt authentically engaged on that level. I suppose that I’m fortunate to truly believe in what I do, and have never felt the need to run away or rebel against this lifestyle, to the contrary, if anything I’ve come to appreciate it, more and more. Still, something was not quite right. Though I’ve never consciously avoided the Rebbe’s teachings, and they were always a part of my study routines, there may have been a disconnect between the activist side and the theological side. In recent years I have been thrilled to discover a new found enthusiasm in the way those teachings come alive for me, resonating with a deeply personal relevance and meaning.

This has led me to another important realization. I’ve learnt that like everything in life stuff happens when its supposed to. We must be open to those possibilities, and the countless ways in which our evolving life experiences are stepping stones for an evolving awareness as well.

The experience of life itself is turning out to be its own kind of Rebbe for me.

Case in point, and very apropos of this subject. A teaching from the Rebbe. According to Jewish law even if one was so poor that they couldn’t afford wine and matzah for the Seder, they still have the obligation to recline on this night to symbolically recall the Exodus.

The Rebbe reads this also from an existential vantage point. Though a person might still be lacking the higher awareness symbolized by the wine and matzah, a light that would enable one to truly live in the radiance of their higher soulful self, still- the symbolic act of desiring that freedom itself constitutes an opening of sorts into that world, a step towards it, that is a form of freedom as well.

When we were young children, the moment Passover was over, we would leave everything as is, hop into the car, and drive to New York where the Rebbe would just be at the tail end of KOS SHEL BRACHA.

What was this?

At the end of the holiday in front of thousands the Rebbe would make Havdalah, and afterwards people would line up with little plastic shot glasses. Thousands would pass by the Rebbe as he poured each of them a drop from his cup and offered them his blessings.

We would usually be the last ones. It was admittedly a bit crazy, but it was a world that vibrated with its own truth, and I’m fortunate to have been able to experience this in my lifetime.

I am drinking from that Cup of blessing till this very day.

Much love

Rabbi Yossi

About the Author
Rabbi Yossi Lipsker is the co-founder and executive Director of Chabad of the North Shore and spiritual leader of the Chabad Community Shul. He can be reached at
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