Out of the blue, he entered our camp surrounded by an entourage of eclectically dressed, vibrant hippies. Some said he was Bob Dylan’s original mentor. Others said he gave Bob Dylan his first hit of acid. Neither group seemed sure of the veracity of their tradition. Both swore he was deserving of their adulation. It was 2008. I was in Wyoming, in the middle of the forest. Diamond Dave Whitaker was the most famous man at the Rainbow Gathering, and he had just sat down on the blue lawn chair in front of me.

At the time, I didn’t know he was a noted American artist, counterculture activist and radio host. I didn’t know that he was one of the first members of The Diggers, an arts group that also gave free food to the needy of Haight-Ashbury. I didn’t know that he had left his family’s home as a teenager in 1957 and hitchhiked 1,881 miles to join the beat poetry scene of San Francisco. I didn’t know that he had grown to be called the Mayor of Haight Street, not for his political perspicacity but for his ability to get people out of jail and prevent turf wars between the punks and the skins in the neighborhood.

I didn’t know any of what I would later find out he affectionately termed his “hipstory.” All I knew was that the hushed voices and furtive glances marked the entrance of a living legend.

“Pssst, I think he’s Jewish,” someone whispered to me. Then my friend Daniel Feld sidled up next to me with a mischievous grin on his face. “C’mon,” he uttered confidently. “Let’s go give him a ‘Shalom Aleichem.’ ” Without waiting for my response, he made a bee-line towards the courtiers sitting around Diamond Dave.

My instinct was to reach out and pull Daniel back. “Is this against some Rainbow rule?” I worried. But Daniel is a force of nature—gregarious, fearless, and with that restless hunger for new experiences that all artistic souls share. We’d made it this far together, and I wasn’t going to let him do this on his own.

We had spent three days driving a U-Haul across the vast American landscape, packed with (literally!) a ton of food, tiki torches, a portable shower, tents, sleeping bags, pots and pans, a big metal barrel, fruit roll-ups, carts, a bicycle, and a Mormon friend named Notice who we picked up in Utah.

We arrived in the middle of nowhere, Wyoming, into a complex of 20+ campsites spread over miles of forest, filled with bears, moose, mosquitos, and 30,000 friendly hippies. There, we built a kitchen from scratch, dug a fire pit, and hosted 1,000 people in the strangest Shabbat dinner I had been to (suffice it to say the dress code was not what one would see in Boro Park).

Unpacking the “Jerusalem Camp” truck, 2008. ©Zev Padway

We had volunteered for this trip to help our friend Zev Padway, manager of the vegan, kosher “Jerusalem Camp” kitchen at Rainbow. Zev is a legend of his own. Oozing with charisma and razor-sharp wit, Zev was formerly a Hare Krishna gypsy who once won the Purim costume contest at Chabad of Berkeley (he wasn’t dressed in costume). He later met Asi Spiegel (pioneer of the largest Passover Seder in the world) who inspired him to create “Jerusalem Camp” at Rainbow to serve thousands of people free vegan, kosher food, coupled with Torah education. Today, he runs a popular vegan, kosher cafe in the mystic city of Safed in the north of Israel, and is co-creator of The Kabbalah Coloring Book in partnership with the preeminent Israeli artist David Friedman.

But this was my first time at the Rainbow Gathering and I struggled to learn Rainbow’s funny socio-economic culture and rules for creating organized disorganization. Technology was discouraged. Money wasn’t allowed. If you wanted to buy something at the Trading Circle, a shiny rock was of much more use than a dollar bill. People gave themselves new names, like Hoot, Human, Tree, Plunker, Gypsy, Wolfman, and Moonflower. Polite salutations were replaced with ideological expressions of peace and harmony like “Welcome home, brother,” “Well gathered,” and “What is your heart song?”

Daniel sang chazzanut to thousands of hippies. I served kosher, vegan cholent to people of all shapes, sizes, colors, and smells. We befriended the Jewish leader of a biker gang of ruffians, who wore a pair of tzitzit we gave him until they were completely threadbare. The guy camping next to us brought his pet wolf, and our friend Notice had recently finished giving us a hands-on lesson in how to successfully escape a charging moose. Incidentally, Daniel named the moose Shaina in memory of his pet donkey. But that story is for another time.

“Shaina” the moose. ©Daniel Feld

Keeping our shared experiences in mind, we approached Diamond Dave. “Welcome home, brother!” Daniel’s clear voice sang amongst the ancient whitebark pines around us. Diamond Dave focused his gaze on us. His eyes glinted merrily. Daniel began doing what he did best. Schmoozing. Diamond Dave was indeed Jewish. He had even lived on a kibbutz in Israel for a short time. But he had never had a bar mitzvah.

My Chabad instincts started to tingle. I rushed back to my tent and grabbed my tefillin. The Talmud teaches that putting on tefillin is among the greatest positive mitzvahs in the entire Torah.1 The opportunity was golden.

Diamond Dave was delighted. He sat serenely as Daniel wrapped the straps around his arm. We sang the Shema with him. He closed his eyes, and the midday sunlight glinted off the jet-black tefillin box as if it were a crown on his head. Birds chirped above. The hippies around us watched in awe. We were all feeling the moment.

Diamond Dave opened his eyes. They were wet around the edges. Daniel and I began to sing mazal tov, customarily sung in synagogues around the world. Fruit roll-ups were thrown, and Diamond Dave tapped his fingers absentmindedly on his knee as we clapped, danced and pranced around him.

Daniel Feld (right) putting Tefillin on Diamond Dave (left). ©Zev Padway

The Baal Shem Tov taught that everything one sees and hears is a lesson in how to serve the Creator. We had a hippy legend sitting in front of us. He must have something to share. As I removed his tefillin I asked him, “Diamond Dave, what’s the secret to life?” It seemed he had been waiting for this. He leaned back and smiled.

Punctuating the air with his right hand like a maestro delivering his cadenza, he delivered four verses:

Cast a wide net
Find the common thread
Let life flourish
Don’t panic, just keep it organic

It was exact. Every word was needed; each line complete.

I thanked him for his wisdom. A few minutes later, he disappeared into the woods from whence he had come, surrounded by his entourage.

The experience with Diamond Dave lasted a few minutes, but from that moment until this very day, I have found myself repeating his lesson. Whether I’m counseling someone about dating, career advice, spiritual growth, or a host of other human dreams, I often find myself quoting Diamond Dave. I thought we had given him the gift of a bar mitzvah, but he had given us the gift of sage advice. As Diamond Davewould say, it’s all about “doing more together.”

The Torah teaches, “You shall rise before a sage and you shall respect the zaken, etc.”2 Rashi, explains that zaken, the ancient Hebrew word for elder, is an acronym for three Hebrew words: “Zeh kana chochmah,” meaning “this person acquired wisdom.”

On that summer day, under the canopy of the Creator’s glorious sky and trees, I learned that sages come in all forms.

The Rebbe was once asked by an elderly woman (younger than him) how he could stand and greet people for hours on end without tiring. The Rebbe replied with a smile, “Every soul is a diamond. Can one grow tired of counting diamonds?”

Thank you, Diamond Dave.