In Jewish tradition, a ritualized first haircut for boys at the age of 3 is called upsherin or upshernish.

The tradition has been traced to Rabbi Isaac Luria, a 16th-century mystic in Safed, Israel. Luria’s disciples wrote their revered teacher went to Meron–the supposed tomb of Rabbi Shimon ben Yohai (another great mystic)–to cut the hair of his young son “in accordance with the well-known custom.”

In modern times, the practice of upsherin has been confined largely to the Orthodox community. But, in recent years small numbers of Jews of other denominations have adapted the ceremony.

‘Gimme a head with hair’

Leo Goldenberg, now 9 years old, had his upsherin chronicled in a 2016 issue of the Jewish Light’s OY! Magazine. His younger brother Ami also had an upsherin when he was 3.

His parents first thought about Leo’s hair-cutting ceremony shortly after his birth when his male cousins had upsherins in Israel.

“It’s a neat rite of passage for sending a boy off into the world as a learning, growing and studious being,” said Leo and Ami’s mother, Caroline Koenig Goldenberg.

Before Leo’s ceremony, he attended two upsherins before his own, so he knew what to expect.

Back on that day in 2016, Koenig Goldenberg stood ready with a plastic bag, opened to accept her son’s newly cut strands. As a remembrance, she would keep some. Had Leo’s fine hair been thicker, she said, she would have donated it, as others often do, to groups that make wigs for youngsters with medically caused hair loss.

Apparently, six years later, Leo’s hair has grown thicker.

Upsherin redux

Fast-forward to this past Valentine’s Day, Feb. 14, when the end result of Leo’s upsherin experience was his decision to make that donation after growing his hair out a second time.

While there isn’t anything particularly religious about this decision, it definitely counts as performing the mitzvah of giving tzedakah (charity).

“Even though we regularly model giving tzedakah and the boys donate to charity in lieu of one of their Hanukkah gifts every year, donating their hair is tzedakah that is not monetary and is truly a sacrifice from their own hearts,” said Koenig Goldenberg. “Leo is even thinking about recruiting some friends to join him in donating as a mitzvah project for his bar mitzvah. It’s not until 2025 so there is plenty of time.”

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Leo Goldenberg

Leo chose Wigs For Kids as recipients for his hair because wigs are provided to children in need at no cost to the families,” said Koenig Goldenberg.

The cut took place at the Kink Hair Salon in Clayton, which is a Wigs for Kids ambassador salon. Here they do the cut and handle the donation by sending the hair to the organization. The process took over two hours.

“We are so proud, this was entirely Leo’s decision and he was determined to follow through,” said his mother. “It felt so good as a parent to watch him give up such a huge part of himself. He was able to write a letter to his recipient and in the letter, he wrote ‘my hair makes me feel strong, I hope it makes you feel strong too.’”

On Feb. 15, Koenig Goldenberg said Leo was excited to go to school and show his friends his new hair. He says it feels weird to have short hair, but he has no regrets.