Robert Chester, insurance manager and civic leader in Carle Place, dies at 92

Robert Chester left his mark on Carle Place during his half century there, from rescuing a baby out of a burning house to championing an expansion to the Carle Place High School to ease overcrowding.

With his funny, calm personality, his family said, he succeeded at his brother’s Chester Insurance as partner and manager and also as president at several Carle Place service organizations — the American Legion, Kiwanis Club and Chamber of Commerce, the civic association.

“Everyone kept saying he wears his emotions and everything on his sleeve,” said daughter Christine Dawson, of Carle Place. “It’s easy to be president when you’re talking to someone and they can trust you because there’s no hidden agenda.”

He did all this, as well as serving on the school board from 1968 to 1973.

The Carle Place Middle/High School stands as a testament to his persistence and foresight as a school board member. Some residents protested against building an addition onto the high school in 1969, his family said, but he knew it was needed to ease overcrowding. The school was designed for 975 students, but enrollment was 1,131 in 1969 and projected at 1,357 in 1971, according to a school board newsletter, which was also his idea.

Chester, who moved to Carle Place in 1956, died in his sleep Nov. 20, two weeks after being diagnosed with an acute form of lymphoma. The retired insurance salesman was 92 and had lived in a 55-plus community in Riverhead for the past decade.

He had called himself an “oops baby,” the youngest of seven, born during the Great Depression and raised in a Brooklyn two-bedroom home, said his daughter Diane Arpaia, of Cutchogue. Sometimes, his mother would have to get food from the church, a fact kept secret from his father to preserve his pride, she said. He was the last kid in Brooklyn who had to wear hand-me-down knickers when they were out of style, he joked to relatives.

His sisters, much older than him, babysat him as they worked, and while they coddled him, their “carefree” affection shaped his personality, family members said.

To his children, he was open with his emotions and recounted love stories of his wife, Wanda, whom he had met at insurance school and married in 1957. Family members described the couple's relationship as one of giggles, twinkles in their eyes and teasing. He’d start off some mornings by joking to her, “I’m sorry for what I’m going to do wrong today.”

Many a night Chester would bring his three children to bed early — one in each arm and one on his back — so he could leave to organize community events, his family said. For years on Memorial Day, residents would watch the American Legion parade, then flock to Salisbury Park, now called Eisenhower Park, for a picnic with free food, sack races and other fun — his idea, his children said. He was master of ceremonies for 10 years for the Frog Hollow Frolics, a talent show to raise money for school and community groups.

“He was very gregarious, very friendly and everyone knew him,” Arpaia said.

Perhaps his most famous act was what the Carle Place fire department called “exceptional heroism” on April 6, 1965. Passing by a house, Chester noticed it was burning, and racing inside, he rescued a baby from its bedroom and helped the child’s mother get out, his daughter said. When he learned an older man was on the second floor, he got a ladder and helped the resident climb out a window.

As Robert and Wanda grew older and faced challenges, they supported each other with code words, said granddaughter Ali Dawson Brown, of Greenport. For example, she said, “Apple” meant he or she had already told the story to the same people. Wanda Chester died in 2012.

Even in his last weeks, Chester constantly told family members he loved them, that he was born under a lucky star and to “be happy, you deserve it.”

“Being close to him felt like a true belonging,” his granddaughter said. “His presence naturally drew the family together, creating a sense of home wherever he was.”

Besides his two daughters and granddaughter, he is survived by his son, Robert Chester, of Sea Cliff, and five other grandchildren.

A Mass was celebrated Nov. 24 at St. Isidore Roman Catholic Church in Riverhead, followed by a private burial.