Herbie Kupersmith is turning 80, and Chelsea is preparing to celebrate in a big way.
On July 27, the Saul Nechtem Gymnasium will host a major gathering honoring one of the city’s most generous and influential citizens. The occasion marks not just a milestone birthday but a lifetime of meaningful contributions to the community.
Among those attending will be Herbie’s wife, Cookie, along with their daughters Karyn, Stacey, and Marci, and grandchildren Michael, Jackie, and Colin. His proud family represents just the beginning of a guest list drawing people from across the region.
Mentorship and Mother’s Wisdom
When Herbie was two-and-a-half years old, his mother Sally brought him from Brooklyn to Chelsea, where he would spend his formative years as an only child.
“We lived on 13 Michael’s Place, which was
off Williams Street,” said Herbie. “We were 35 feet away from
the Chelsea Dump.”
Throughout his youth, four highly respected Chelsea figures would serve as valuable mentors alongside his mother’s guidance.
“fblikebutton_button” Herbie explained the profound influence of these men: “Hugh J. McLaughlin, the former mayor, Julius Zeff, teacher and basketball coach, Paul “Choc” Glazer, community leader and head of the YMHA, and Harry Coltun, legal counsel for the Mass. House of Representatives – those four people, along with my mother – made it possible for me to be the person I am today.”
His spiritual foundation began at the Walnut Street Synagogue, where he was bar mitzvahed in 1952. That connection has endured throughout his life as he has worked tirelessly to support and fundraise for the historic congregation.
His bar mitzvah held particular meaning because of three handwritten letters from his mother. “Never drink the cup dry – leave some for
other people,” Herbie recalled. “No. 2 was, if you’re going to do something, do
it because you want to do it, not because you want to get accolades. And No. 3,
my mother wrote, ‘I want you to be a giver, not a taker.’”
A passion for athletics developed early. Playing as starting guard for the Williams Junior High School basketball team, Herbie helped the squad achieve 27 consecutive victories. Later, he played basketball at Chelsea High School under Coach Saul Nechtem.
Building a Business Career
Following his high school years, Herbie entered the workforce selling shoes for Nunn Bush at Kennedy’s and Filene’s.
Before settling into a long-term position, he worked in various sales roles.
His opportunity came at Bobbie Brooks, a junior sportswear company, where his charisma, integrity, street smarts, honesty, common sense and magnetic personality enabled him to set sales records and ultimately command the entire Boston territory. For 25 years, Bobbie Brooks remained his professional home.
Life and Family
A blind date led to meeting Cookie, who became his wife in May 1965.
The couple established their household in Malden before relocating to Marblehead in December 1965, where they have remained.
Their three children—Karyn, Stacey, and Marci—all completed college. Two grandchildren, Michael Walsh and Jackie Walsh, graduated from Brown University, while a third, Colin Walsh, attends Elon College in North Carolina.
Celebration and Gratitude
This birthday celebration will serve as a testimonial, bringing together countless individuals eager to express their appreciation for Herbie’s generosity and encouragement.
The gathering will include former athletes like David Siggers, a standout basketball player from Marblehead and Stonehill College; coaches such as John DiBiaso; Walnut Street Synagogue congregation members; business associates; longtime friends including Lennie Nelson; planning committee co-chairs like Minna Karas-Marino; and city officials like Leo Robinson. All will come to say “Thank you,
Herbie,” for such a transformative and encouraging influence.
The event will be catered by Rita’s, with comedian Brad Mastrangelo performing and DJ George Athas providing music. Former City Manager Jay Ash will address the audience during the program.
“It should be a nice evening,” Herbie stated with characteristic humility.
Reflecting his generous spirit, all birthday party donations will benefit a scholarship fund established for Chelsea students.