Jerry Glassberg is a retired businessman, closing in on five decades of living on Shelter Island. Now in his 80s, he’s in the middle of his second act as a writer and sculptor. “I retired very early,” he said, “Terribly early.”
Considering his mother lived to 106, Jerry figured he might need a second career.
He grew up in Long Beach and met his wife-to-be, Tamara Chapman, on the beach. He was a lifeguard who looked pretty great in swim trunks. She was a ballet dancer from Ohio who had moved to New York to dance with the internationally renowned Ballet Russe de Monte Carlo.
“I met her, and within half an hour it was like a cartoon, like someone banged me over the head,” he said. “I was crazy in love with her.”
Tamara toured extensively with the Ballet Russe, and performed in the original Broadway production of “Paint Your Wagon” in 1951/52. They married in 1953. Jerry described their relative stations in life with his hands, “I’m here,” he gestured low. “She’s up there. But you have on a lifeguard suit and a whistle, you can talk to the most glamorous woman in the world.”
Not long after they married Jerry came close to dying. Not quite recovered from an illness that left him bedridden for days, he decided to go to work on a Saturday. When a swimmer needed help, he took over the rescue.
But he got to the swimmer in trouble, just as he realized his illness had sapped his strength, and was suddenly in need of rescue himself. “I said to one of the guys, ‘Take over for me,’” he remembered. “I was much too macho to say, ‘I’m sick, help me in.”
He swam away, but lacking the strength to swim to shore, he began to sink, and when he came up, didn’t have the breath to yell for help. “I gave up,” he said. Going down for what he thought was the last time, he found he was in three feet of water, and crawled to shore. “I never worked another day as a lifeguard,” he said. “I was too embarrassed.”
The epitome of a self-starter, Jerry decided to create his own business from the ground up, “I wrote a letter to 35 pottery and dish manufacturers and said I’d like to represent them, and a couple of them answered,” he said. “I’m a big talker. I walked the streets of Brooklyn with 60 pounds of samples.”
Early in his career, Jerry remembered being in a buyer’s office when an older salesman came in and the buyer — young and brash — treated the older man with disrespect. “The buyers, they have the power,” Jerry said, “I remember standing there and thinking, ‘I’ll never get in that position. I’ll never get where a little snapper can talk to me like that.’”
By the early 1970s, Jerry’s import/export pottery business was flourishing, he and Tamara were living near the city, and they started to look for a weekend home. Visiting Greenport one day, Tamara suggested they take the ferry over to Shelter Island. “It was like when the Wizard of Oz goes into
Technicolor,” Jerry said. “Wow, golf course, tennis courts, sailing.”
They found one fault with Shelter Island, Jerry joked. “Your income goes down, because you start taking off Fridays and then you start taking off Mondays.” In 1985, Jerry retired and they began living full time in a house they had built on Lakeview Drive.
The couple had two children, Leslie and Neil. Their daughter Leslie worked for NBC as a production manager for the Seoul Olympics and for Saturday Night Live. After more than a decade at NBC Leslie told her father, “I go to the bathroom and 10 people follow me … I’m thinking of quitting.” She left NBC to establish a successful yoga practice. Neil is a businessman based in Bahrain and is the father of four.
Upon retirement, Jerry rediscovered his love for sculpture, a form of artistic expression he’d enjoyed earlier in life, but had put aside. He did several commissions in the 1990s — portrait busts of notable people, such as Lester Brooks, former president of Timex Watch Company, and George Willis, a professor at the University of Toledo. He has also depicted notable Shelter Islanders, including Jack Ketcham and Dr. Peter Kelt.
In 2001, Jerry endured great sadness in an otherwise happy and fortunate life when Tamara passed away at the age of 70 after an 18-month illness. They had been married for 47 years.
Jerry has created garden sculptures for a number of private homes on the South Fork and Shelter Island, as well as nudes of every size and bearing. Some of his works are on display in his own yard, including a large white rabbit at the head of the driveway and a naked pair of lovers out by the patio whose anatomy conveys the excitement of their romance. Jerry smiled in recollection of the effect that sculpture had on a Garden Club party touring the property.
Jerry has also written and self-published three books of both fiction as well as non-fiction, and is working on a fourth book on the life of Frank Seiberling, co-founder of the Goodyear Tire and Rubber Company.
As for the future, Jerry said, “I’m open for business.”