Last month, 52-year-old Brian Sherman was tapped to fill out Jay Card Jr.’s term as Superintendent of Highways and Commissioner of Public Works.
On an island with a lot riding on both, it’s a vital role, and Brian took it with the understanding that he would run for the office in November.
“I’ve never run for office before, and I feel great about it,” he said. “I think I can do some good.”
The Sherman family goes back a long time on Shelter Island. They used to own the Havens House — one of a handful of pre-Revolutionary War era homes left — and took in boarders before and after World War II. They raised strawberries on a farm that extended behind the house all the way to Baldwin Road.
The Sherman family home became the Island’s family home when Brian’s great-grandmother, Alice McNamara Sherman, decided to sell it to the Historical Society under an agreement that allowed her to stay for the rest of her days.
She lived there until her death in the early 1970s, and Brian remembers visiting her when he was young enough to appreciate a treat.
“She had those hard gumball candies she used to give me,” he said.
Brian’s family is still a strong presence here. His parents, Judy and Herb Sherman, and his Uncle Hoot and Aunt Joanne, still live on the Island. He has three siblings; Carla, who lives in New Hampshire; Rebecca, who married Islander Donald Clark, and lives in North Carolina; and Michelle, who married Ray Congdon, and lives on the Island.
After graduating from Shelter Island High School in 1985, Brian worked as a trucker full time, “until I settled down.”
Even after he began working for the Highway Department, driving a truck was a good way to supplement his income, and he continued driving two or three nights a week, taking loads of local seafood from Montauk, Mattituck and Greenport to the Hunts Point market in the Bronx.
His first marriage, to Laura Goody in 1986, ended in divorce. They shared custody of their daughter Jessica, who grew up on Shelter Island, went to nursing school and lives near Charleston, South Carolina.
Frank Klenawicus hired Brian at the Highway Department in the late 1980s and a few years later, when an opening came up at the landfill, Brian took it. “I started working for $6 an hour,” he said. “No one wanted that job when I took it. I needed the benefits.”
In those days, the town did its own paving, and Brian often ran the roller. When word came down from the state that towns had to stop burying garbage, Brian worked to cap and close the landfill.
When the town set up a lottery to find qualified local people interested in buying subsidized affordable houses on Bowditch Road, Brian was in.
In 1991, Brian met Gina Giannone when they were both bartending at a party at the Island Boatyard. Gina was from Mattituck, where her family ran Giancarlo’s Pizza and the Main Road Tavern. They married in 1995.
Gina has faced considerable health challenges over the years, including a long hospitalization and recovery in the early 1990s before their children, Taylor and Isabella, were born, and more recently multiple sclerosis, a chronic condition she’s struggled with for more than a decade.
Taylor graduated from SUNY Morrisville and now works for a diesel company. Isabella, who was born in 2000, is a freshman at Norwich University, the oldest private military college in the country.
Her choice of a college was a surprise. “We never would have thought,” Brian said. “Uncle Hoot was career military, and Uncle Scott, and my sister’s two kids just got out of the Navy. But she said, ‘I don’t think so.’”
A trip to Washington to attend his aunt’s funeral at Arlington, and visiting another aunt who works in the FBI building, stimulated Isabella’s interest.
A volunteer firefighter for 20 years, Brian served as Fire Department chief in 2000. It’s a family tradition. His father recently retired from the force at 83. But Brian predicts that within 20 years, a volunteer department won’t be viable here, and will give way to a professional force, a change he thinks is necessary.
“We wouldn’t be at risk of slower response. Now, you’ve got to go through medical testing and training, rules and regs are constantly changing,” he said. “Our guys have to do fundraising. You don’t see that anyplace else.”
Brian would like the town’s plans for dealing with the looming challenge of solid waste to get a lot closer to center stage. “Nobody ever talks about it. In another five years, Brookhaven landfill is going to close and that’s where all our construction debris goes,” he said. “We need to be prepared.”
He sees more the town could do to operate in a sustainable way. “We’ve finally got money in the budget to put a roof over the baler and solar panels on the buildings,” Brian said. “That would start the town being a little greener. Here on the Island, we take care of each other.”
Favorite place on Shelter Island? My backyard.
Favorite place not on Shelter Island? Termini, Italy.
When was the last time you were elated? When I saw Issie at college. We couldn’t be prouder.
What exasperates you? Stupid people driving.
What is the best day of the year on Shelter Island? Labor Day. Not that I don’t like everybody, but it is a sigh of relief.
Favorite movie or book? “The Searchers,” with John Wayne.
Favorite food? Spaghetti and meatballs.
Favorite person, living or dead, who is not a member of the family? George Washington.