10 Lessons I Learned From Rabbi Sholom Ber Lipskar

By Rabbi Ruvi New, Director of Chabad of East Boca, Florida

There’s an old cynical Jewish joke sourced in the names of this week’s Torah portions – “Acharei Mos/Kedoshim” – lit. “holy after death” – that some people are suddenly thought of and remembered as holy only after their passing. Not so much during their lifetime….

Such is not the case, as I and many around the world, reflect this week on the life of Rabbi Shalom D Lipskar OBM, who passed away this past Shabbos. His life was saturated in holiness and that was plain to see for anyone that knew him.

The Hebrew word “kedoshim” connotes not only “holy” but “unique,” distinct,” “special.”

It is in the spirit of that definition that I share with you what I learned from Rabbi Lipskar. Not because he wasn’t holy in the conventional sense of the word, but because holiness alone is not what made him so special. Holiness can sometimes mean abstract, abstruse, detached, totally transcendent. Rabbi Lipskar’s version of “Kedoshim” – holiness – was also very human. His idealism was grounded. His vision was practical.

I share my thoughts and reflections as a fellow Shliach/emissary of the Rebbe, a role Rabbi Lipskar excelled at in extraordinary ways, making him, for me at least (and I suspect many of my colleagues) an iconic Shliach. In many ways direct and indirect, he was my mentor, role model and inspiration.

Much has been and will be written and shared about Rabbi Lipskar. What follows are the life lessons I personally learned from him and perhaps you will learn from them too.

THE LEGEND
Before I ever met Rabbi Lipskar personally, I encountered his name on a… menu. In the eighties the go-to dairy restaurant in South Florida was Sara’s on 125th St, on the west side of the causeway that goes to Surfside/Bal Harbor. Sara’s was famous for, among other things, my favorite – the shmopper – a cheeseburger made with soy. On the salad menu of Sara’s was the “Rabbi Lipskar Salad.” Don’t ask me what the ingredients were, but I remember thinking, man, to have a salad named after you? – that’s next level. This man is a legend!

IT’S SERIOUS “BUSINESS”!
My first personal encounter with Rabbi Lipskar came in the early nineties when I was a rookie Shliach in Marietta, Georgia, a suburb of Atlanta. Like many fellow Shluchim (of that time) I came to Georgia high on inspiration, anxious and excited to share the Rebbe’s vision with the world.

But I was pretty low when it came to the nuts and bolts of building an organization. There was no training for Shluchim in those days and you were expected to figure it out as you went along. Aside from lacking organizational skills, I was (and still am) a reluctant fundraiser. Making the “ask” never came easily or naturally. (Ok it’s gotten a little better over time BH)

When an invitation came from Rabbi Lipskar to attend a one-day fundraising seminar in Miami with himself and Mel Landow, a philanthropist that he had become very close with, (that was amazingly and Providentially featured in JEM’s My Story this past Shabbos on the day of Rabbi Lipskar’s passing) me and my brother Rabbi Yossi New, who was already a bit of a veteran but figured he could always learn more, jumped at the opportunity.

We flew down on Sunday morning and quickly settled into a modest storefront on Harding Ave that was The Shul of Bal Harbor, for the seminar. I can’t claim to remember all that much of the seminar, but what I do remember is the impression Rabbi Lipskar made on me. He evinced seriousness, that Shlichus (being a Chabad emissary of the Rebbe) was “serious business.” If you take the mission seriously, people will take you seriously. You have to be organized, strategic and accountable. Accountable to time and accountable to donors.

Mel led most of the seminar and I vividly recall him preaching about the yellow pad and the daily task list. Every day you should have a list of tasks written on your lined yellow pad and check them off as they are completed. Learn how to prioritize tasks and defer if necessary but never leave a task uncompleted. The daily task list, I later learned, was a strategy that my father strictly adhered to throughout his decades long business career.

OVER THE TOP – DARE TO THINK BIG!
The small storefront we sat in was in the shadows of The Shul that was under construction on Collins Ave. The sight of the shell of the building alone was awe inspiring – testament to Rabbi Lipskar’s big, bold vision and “over the top” attitude. The Shul was a game changer for Chabad worldwide, especially in the US. It was a trailblazer and model for Shluchim for whom Rabbi Lipskar had blazed a new path, broadened the scope of what is possible, daring every Shliach to think big. Much bigger than many would have ever thought to go. Today there are many Chabad Houses that actually call themselves “The Shul” modeled after The Shul of Bal Harbor. The awe, inspiration and aspiration I felt that day as I beheld this grand and majestic building never left me.

When I first contemplated a capital campaign in Boca and wanted to get buy-in from the community, I asked Rabbi Lipskar if he would come and speak. He readily agreed. I wanted people to hear from a real visionary and community builder, to expand their horizons and conceive the possibilities of what we could build. Rabbi Lipskar delivered the goods…

THINK… SMALL!
A story Rabbi Lipskar often shared at Shluchim conferences was how at a “Yechidus” – private audience with the Rebbe – together with his extraordinary partner Rebbetzin Chani Lipskar may she live and be well, he reported to the Rebbe on some of his successes, accomplishments and achievements in Miami. As the Yechidus drew to a close, he could sense that the Rebbe was waiting for something more. He couldn’t think of what else to share.

The Rebbe asked him “and what about the young girl you wrote to me about recently?” I don’t recall the exact circumstances but Rabbi Lipskar in one of his regular written reports to the Rebbe, had made mention of a certain young girl in his community and a struggle she was having. The Rebbe was waiting to hear how she was faring.

Rabbi Lipskar recalled how stunned he was by the Rebbe’s caring and sensitivity toward this girl and realized how the “big” programs, “big” accomplishments, and “big” building, should never eclipse being attentive and sensitive to a “small” young girl. In the Rebbe’s “big” worldview, every “small” individual is a world.

The story became a benchmark story for Shluchim. No matter how big your organizing grows, the big picture ought never eclipse the small one.

DON’T FORGET THE FORGOTTEN
In 1981 Rabbi Lipskar founded the Aleph Institute, an organization that provides material and spiritual support and advocacy for Jews in prison (and for Jewish military personnel). Jews in prison are a largely unknown, unheard of, and all but forgotten population. The Rebbe didn’t forget them and entrusted Rabbi Lipskar with the task of building an organization to support them.

The Aleph Institute leveraged the presence of Shluchim in cities, suburbs and small towns throughout the US. Like many other Shluchim, I found myself becoming a prison chaplain in a Federal prison and in state and county jails as well. Aleph supplied the names and locations of inmates, as well as support materials, and kosher food. For me, entering into this very unknown world was a life changing experience. It’s one thing having a Torah class and conducting a service in a Chabad House, it’s quite another doing it in a prison. For many of the inmates, I was the only visitor they had and many deep and strong bonds were forged between them and myself, and more importantly between them and G-d. On occasion Ahuva would join me when I visited women’s prisons resulting in her having some special correspondence with inmates who so appreciated that they were not forgotten. My experience as a chaplain reminded me to never forget the forgotten.

SELL SUBSTANCE. BE A CONTENT PROVIDER!
Back in the eighties, when the Lipskars first moved to Bal Harbor, the signature program of The Shul was Rabbi Lipskar’s Tuesday night Torah class. It became something of a legend in Chabad circles. Rabbi Lipskar was a trailblazing Torah teacher. Long before the Jewish Learning Institute changed the landscape of adult Jewish learning, Rabbi Lipskar understood that the real key to reaching the soul of a Jew is through Torah. Rabbi Lipskar was one of the pioneers of teaching Torah in a language that was relatable to the modern and sophisticated Jew. In many ways the Tuesday night class laid the foundation for what would become the revolution of Jewish life in Bal Harbor.

Rabbi Lipskar reminded me and many other Shluchim that our job is to sell substance – to be content providers – as in teach Torah. That people don’t need a Shliach to keep them informed of the news, to offer political commentary or be familiar with the latest crazes in pop culture. (He wasn’t advocating that a Shliach should be clueless as to what is happening in the world, but as I once heard him say: reading five minutes of headlines of the Wall Street Journal will provide you with all you need to know of what’s going on in the world). First and foremost the Shliach must be a teacher and purveyor of Torah’s wisdom, and use language that is relatable and resonant. Nothing penetrates the soul more deeply than Torah.

COMMUNICATE AUTHENTICALLY
Aside from his oratory skills, he had a deft pen. Long before AI, he was generating letters that were a fusion of meaningful content and at the same time had a decisive personal touch.

I always marveled how he knew of my own personal family Simchas or loss and took the time to write and convey a meaningful and personal message.

He would always sign his letter with: “ with Torah blessings I remain….” His consistency of always infusing correspondence with content, speaks of someone who was deeply and authentically connected to these ideas.

CHERISH THE MITZVAH
While Torah penetrates the soul, Mitzvahs envelop the soul and every Mitzvah creates a powerful and unbreakable connection between the person and G-d. The value of singular Mitzvahs was a core teaching of the Rebbe and theological basis for the Mitzvah campaigns. Perhaps the most ubiquitous of them is the Tefillin campaign, one that Rabbi Lipskar excelled at.

It’s not always easy or comfortable to ask someone to put on Tefillin. For most of us, our natural impulse is to mind our own business and leave others alone, especially when it comes to their spiritual life. To engage another in an unsolicited offer to do a Mitzvah, and to do it consistently and not relent as you grow older, you have to be coming from a place of deep seated conviction that this Jew’s singular Mitzvah really matters. Rabbi Lipskar lived and exemplified that conviction.

LIVE WITH MOSHIACH IN REDEMPTIVE CONSCIOUSNESS
In an interview about the coming of Moshiach, Rabbi Lipskar said: “In the past we were waiting for Moshiach, now Moshiach is waiting for us.” Start living now in Moshiach/redemptive consciousness, he said. He didn’t just preach it, he did it.

So what does that type of consciousness look like? For a Jew it means embracing our chosenness and bringing light, clarity and G-d consciousness to the world around us. At a Farbrengen in our Chabad House a few years ago, Rabbi Lipskar spoke about how even chance encounters with people can be impactful. Bring G-d awareness into everyday encounters and conversations, he said. When the person at the supermarket check out asks you how you’re doing, be sure to reply “thank G-d” and be sure to ask how they are doing and try to share something meaningful. Encourage people to be charitable and when possible teach the Seven Noahide laws to gentiles.

Again, these were not Rabbi Lipskar’s original ideas per se, they all came from the Rebbe. But what was unique was the passion with which he lived and practiced these ideas, losing none of his passion and idealism with the passage of time.

Messianic prophecies speak of a world of plentifulness and abundance, so in very practical terms, living with Moshiach means living with an abundance mindset. Here’s a very practical illustration of that. On a number of occasions I met with Rabbi Lipskar to discuss projects I was working on, to have him weigh in on their merit and to ask if I could solicit some of the members of the Shul that I thought might be interested in supporting the project.

Rabbi Lipskar never restricted me from approaching his members for funding. In the world of nonprofits and fundraising that is huge and rare. Understandably fundraisers are protective of their supporters. To gladly share a donor is to live in an abundance – redemptive mindset in the most real way.

CHASSIDIC CLASS
Rabbi Lipskar’s demeanor, down to the way he dressed, was a unique combination of Chassidic and class. Elegant but modest. Classy yet understated. He had a unique elegance and magnetism about him and demonstrated that you can be current without being compromising.

LOVE FOR THE REBBE
The first time I saw Rabbi Lipskar was probably around 1985 at Mincha services with the Rebbe in 770. It was just a regular mid week afternoon, no special holiday or occasion. The word among us Yeshiva students was that for Rabbi Lipskar, just to observe the Rebbe walking in and out of services, pray with him on a regular Wednesday, and fly right back afterwards, was worth the round trip flight from Miami and enough to recharge his battery.

In the late eighties when the Rebbe would receive thousands of people every Sunday at the famous “dollars” line, Rabbi Lipskar was often seen alongside supporters and members who he brought with him to receive the Rebbe’s blessing.

The Rebbe’s passing in 1994 did not diminish his love and connection to the Rebbe. He told me that he would often take the last flight out of Miami to New York, spend the night at the Ohel and fly back on the first flight out. He shared with me that his first annual board meeting with his executive board took place in a house near the Ohel. He was the first to bring large groups to the Ohel and trailblazed what has become a staple program for many Chabad House communities around the world. After I saw a video of one of his trips “Journey of Souls,” I too launched an annual trip for our community to the Ohel each year before Rosh Hashana which we dubbed Soul Trek.

His love for the Rebbe came from the core and was overflowing and evident to anyone who interacted with him. And seems to have only grown over time.

In one of the entries of Hayom Yom – a compilation of Chassidic mediations, it says that the greatest evidence of love is when you love what your beloved loves. Rabbi Lipskar loved what the Rebbe loved. He had a deep and passionate love for the Land of Israel, the People of Israel, the Torah of Israel and the G-d of Israel.

For me, hearing Rabbi Lipskar, being around him, always uplifted me to what Chassidim call being a “Tefach Hecher” – “one handbreadth” higher than the world. Less tethered to the world, more bound to why we are here. Less defined by the world around us. More defined by the One Above us. It is “Kedoshim” at its finest – holy/distinct/idealistic/visionary yet grounded, practical, transformative.

Rabbi Lipskar’s legacy will continue to guide, inspire, uplift, invigorate us all to live Over the Top – a Tefach Hecher.

May his relentless drive for redemption be realized now!