Back Again: From Challah to Tefillin to Yeshivah

Illustration Photo: Rabbi Yossi Denburg with CTeens

One Friday morning, Boca Raton Shliach Rabbi Yossi Denburg was manning his weekly ‘challah corner’ mivtzoim stand near a local public school. A single short encounter, quickly forgotten, ended up making a long-term effect.

By Shterna Karp for Ami Magazine

With a loud ring, the last Friday bell rang on the campus of Spanish River High, a public school in Central Boca Raton, Florida. Rabbi Yossi Denburg was across the street, waiting to greet the students who would soon walk by as they escaped for the weekend.

Every Friday, rain or shine, sun or none, the rabbi set up his booth, the Challah Corner, outside the school. The small table, decorated with signs like “Do a Mitzvah” and “Light Up the World,” was always laden with Jewish basics—tefillin, Shabbos candles, and small loaves of Shainy Denburg’s fresh challah. 

Rabbi Denburg watched as the pedestrian signal on the corner of Jog Road and Regency Court turned from red to white, waiting for the street corner to swell with students rushing out of the brick building. 

As soon as they passed his booth, Rabbi Denburg would offer them the chance to do a mitzvah. The boys could stop to put on tefillin and say Shema. The girls could take some candles to light at home. And all were invited to enjoy the delicious challah. 

That particular week in 2019, Rabbi Denburg had guests at the Challah Corner. His father-in-law, brother-in-law and grandfather were in town, and they had joined him on his weekly jaunt. The four men were a sight in the hot Florida afternoon—a few black hats and jackets in the midst of a huge crowd of T-shirts and shorts.  

With the students spilling out all at once, the Challah Corner was usually hectic. On that Friday, Rabbi Denburg didn’t even have a chance to snap a single photo. 

Which is why he was surprised when he got a WhatsApp message two years later from a fellow Boca Raton Chabad shliach. It was a picture of Rabbi Denburg’s grandfather, Rabbi Avraham Glick, who had been at the Challah Corner that day, putting tefillin on a teenager. 

“Huh?” Rabbi Denburg typed back. “I didn’t take any photos when my grandfather was in town. How do you have this picture?” 

“Josh sent it to me,” the shliach wrote back. 

“Who’s Josh?” 

“The kid in the photo. He came to the Chabad House today. It was his first time here.”

The shliach told Rabbi Denburg that Josh had never set foot in a shul before. He hadn’t gone to a Jewish preschool or to Hebrew school. All he knew about Judaism was…nothing. Nothing at all. 

But when he started high school, he had questions. Why did bad things happen to good people? Was the Torah an ancient text or a modern blueprint? How do we know what the truth is?

Josh grappled with these concepts for a few months—until he realized that there was a place with answers. There had been that day, years earlier, when he’d stopped to put on tefillin with the rabbi at the Challah Corner. Josh googled “synagogue” and then showed up at the door of Chabad of Boca.

Out of the dozens of shuls scattered around Boca Raton, he had chosen the one where Rabbi Yossi and Shainy Denburg direct teen programming. 

When Josh walked in, the shliach asked if he wanted to put on tefillin

“I did that once before,” Josh said. “And I even have a picture that my friend snapped for me.” He pulled out his phone and showed the shliach a picture of himself with Rabbi Denburg’s grandfather. 

That Thursday, Josh went to the Denburgs’ home for their weekly Supper ’n Study program, joining a group of teens who were eager to learn about the timeless relevance of the Torah’s laws. After the class ended and most of the teens had left for the evening, Rabbi Denburg pulled Josh aside. They chatted for a long while about the class, about Judaism, and about how Josh had found his way to the Chabad House. 

“By the way,” Rabbi Denburg asked before they said their goodbyes, “if I get you your own pair of tefillin, would you wear them?” 

“I’d love to,” Josh said. Tefillin was the mitzvah that had brought him here. Rabbi Denburg rummaged through his Judaica cabinet and brought back a small loaner pair for Josh to use. 

“It’s only until you get your own set,” the rabbi clarified. “I’m going to call the sofer tomorrow and make an order.”

Josh took the pouch and thanked the rabbi.  

The package from the sofer arrived on a Friday morning a few weeks later—a handcrafted set of tefillin with Josh’s Hebrew name, Yehoshua, embroidered on the pouch. Rabbi Denburg called Josh with the good news. “Your tefillin are here,” he said. “When can I give them to you?” 

“I’m in school until two,” Josh replied. “Can I come by your house in the afternoon, maybe around three?” 

It was Friday, which meant that there was a fresh batch of challah rising in Shainy’s kitchen—and that the rabbi planned to spend the afternoon outside Spanish River High School. 

“I won’t be home then,” Rabbi Denburg told Josh. “I’m going to be at the Challah Corner.” 

“Oh, I guess I’ll come by afterward, then.”

“Wait a second,” said Rabbi Denburg. “You know exactly where the Challah Corner is. Why don’t I give you your tefillin there?” 

Which is how Josh ended up back at the Challah Corner, putting on tefillin in the same spot he had first done it two years earlier—only this time, he was using his very own pair.

The Continuing Story

That one mitzvah, tefillin at the Challah Corner, led to more and more. After getting his own tefillin, Josh wanted to learn more about davening, Torah and Yiddishkeit. And when he finally graduated from Spanish River High School, he enrolled in yeshivah.

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