Gerry Siller was in high school when he decided to apply for a job at a new restaurant near home in Massapequa. He’d worked at his father’s deli in Bellmore, so knew how to make a sandwich, and when the hiring manager came out to see if anyone in the around-the-block line of applicants was a short-order cook, Gerry raised his hand. He was hired, and just before his first day on the job, a friend told him the secret of success for any job: “Just have a rag in your hand and always be cleaning things.”
This multi-tasking, continuously-improving way of life has been good for Gerry, from running bars and a restaurant in his early years to a successful landscaping business on Shelter Island, to his time as Town Supervisor from 1998 to 2001.
Gerry has decided to run for another term as supervisor in the November election. “When I did it, I loved it,” he said of his time leading Island government. “It was the best job in the world.”
Eighteen years later, Gerry said some of the same issues he worked on then are still front and center on the town’s agenda, including water quantity and quality, deer overpopulation/tick-borne disease and affordable housing, and he’s ready to take them on.
At his side is Roni Siller, his wife of 43 years. Roni and Gerry both went to Massapequa High School, where they met at a Friday-night party 50 years ago, and have been together ever since. He was president of the Key Club, and a schmoozer. “He would talk to anybody,” Roni said. “He just knocked me off my feet.”
After graduation, Gerry went to the School of Visual Arts to study photography, and Roni studied at Marywood University and became a school teacher. They lived in Massapequa where she taught, and Gerry ran bars and opened a seafood restaurant in Copiague, which resulted in his worst work experience ever. The chef he hired to design and execute the menu suddenly quit a month after they opened, and Gerry had to learn to cook every dish on the menu.
“I was the chief cook and bottle washer,” Gerry said. “In a hot kitchen, with stress.”
Roni introduced Gerry to Shelter Island. Her grandmother was one of the original homeowners in Hilo Shores, on land that had previously been a poultry farm, across from another chicken-producer, Cackle Hill. Roni had been going out to her grandmother’s place for many years when she brought Gerry in the early 1970s. He was impressed. “At the time, there were cows on Menantic Road, and I remember going rowing right off of Hilo and seeing scallops coming up in the water all around us,” he said.
The birth of their daughters persuaded Gerry and Roni to move the family from Massapequa to Shelter Island, where all four girls went to the Shelter Island School K-12 and were active in horseback riding. Kristen studied business in college, She lives and works in Kentucky, and has two children, Grace, 8 and Riley, 13. Meghan, who was valedictorian of her class, went to Connecticut College. She works as an administrator at the Hospital for Special Surgery in New York city and has a child, J.D. (James Douglas).
Molly was the best horseback rider of the family (according to Gerry), and went to the National Horseback competition. She lives in Cutchogue with her spouse and two children, Wyatt and Austin. Katie went to Catholic University of America and is a nurse at the Memorial Sloan Kettering Cancer Center in New York.
Four children with an intense interest in riding meant the Siller family kept horses in the back yard, and sometimes they got out. Gerry got a call one night informing him that his horses were over by Hampshire Farms, almost a mile away. By the time he arrived, the Police Department was there, too, and the officer suggested instead of walking the horses home in the middle of the night, they’d use the squad car. He drove slowly as Gerry sat in the open trunk and the horses walked home behind the car.
When the family first moved to the Island, Gerry remembers people told him that if he was willing to work, he might not get rich, but he’d never go hungry, and he considered that good advice. Gerry worked in landscaping and owns a garden center, and Roni taught home economics at the Shelter Island School.
He was active with the PTSA and then on the Board of Education for 10 years, starting in 1988, during an exciting time in school history. He served on the Board of Ed that removed the superintendent/principal and replaced them with Lydia Axelrod, who would go on to be one of the most popular and successful school superintendents the town has ever known.
“We knew we needed someone who could mend things,” Gerry said, referring to the trouble and controversy that surrounded the previous superintendent/principal. “Lydia was great — she’s still paying attention, and may be reading this — she was a healer.”
The school needed additional classrooms, and the Board of Ed got funding approved for building a new wing with classrooms and an auditorium in late 1980s. It was a bare-bones budget, with Board member Cliff Clark working with an estimator to keep track of costs, and using seats recycled from another auditorium.
Gerry’s work on the Board of Ed only ended when he decided to run for supervisor in the fall of 1987, beating Hal McGee, a popular and well-respected member of the town council.
He set to work implementing and extending the good work of his predecessor in the job, Hoot Sherman. “Hoot got the affordable housing on Bowditch Road and started the Ram Island Causeway from the Army Corps and we followed through on it. We petitioned LIPA and they buried the power lines. We wrote the zoning code and created the near shore overlay district to protect the fragile areas.”
He turned the Recycling Center around from a money drain to a money maker with the help of Brian Sherman’s skill for finding markets for the town’s recyclables. When a funeral home in the center came on the market, Gerry oversaw the purchase of the building as a new Town Hall, allowing the Police Department to emerge from the basement of their current headquarters.
When the time came to run for a third term in 2001, Gerry was the driving force behind a referendum on the ballot to expand the Highway Department property by buying some adjacent acreage. People who liked the idea thought it would provide a site for industrial infrastructure on the Island, but those who opposed it thought it was too high a price to pay.
“To this day, I believe it was the right thing to do,” Gerry said. “The referendum was defeated, and so was I.”
Gerry and Roni have remained involved in the community. They’ve had their share of health crises, including Gerry’s esophageal sarcoma in remission, and more recent serious health problems that Roni is dealing with.
“We lean on each other, and the family,” Gerry said, “and we’re more appreciative of Shelter Island than ever. When we’ve had problems, people have rallied to help us.”
As he enters another election cycle, he’s reminding Islanders that he has always been a strong advocate for affordable housing. What’s new are the models he’s proposing for town and private development of homes for Island workers.
“Darrin Binder bought the A-frames and he is fixing them up for year-round rentals,” he said. “It’s serving a purpose. It’s not a drain on the neighborhood, it’s not a drain on the aquifer.”
He’s also satisfied with the four-apartment house a few doors down from his home that was developed by Janalyn Travis Messer, and is now fully-rented.
“My plan would entail using town-owned land and the homeowners would own their houses. If they sold, they would have equity in the house,” he said. “Start with two houses, and then you can show this is what we are capable of, it’s a good start.”
Not for a minute has he taken the rag out of his hand.
What do you always have with you? A pocket knife.
Favorite place on Shelter Island? The North Ferry, coming to Shelter Island.
Favorite place not on Shelter Island? Anywhere with my grandkids.
What exasperates you? When kids tell me they’re bored.
When was the last time you were afraid? When Roni had a health issue lately.
Favorite movie or book? ‘The Power Broker,’ by Robert Caro.
Favorite food? A good hot dog. It should be a little crunchy.
Favorite person, living or dead, who is not a member of the family? Our neighbor, Eleanor Oakley — upbeat, a real role model.
Most respected elected official? Daniel Patrick Moynihan, he worked across party lines.