Island Profile: Dorothy Ogar, an enduring presence at Town Hall

Dorothy Ogar will be sworn in for another four-year term as Town Clerk in January. Dottie, as she’s called, has served since 1978.

A 39-year-old working mother then, she ran on the strength of 16 years working in the clerk’s office with her mother, Helen Smith. She’s one of the longest-serving elected officials in New York State, just behind Richard Gottfried, an assemblyman who has served 51 years since being elected right out of college.

When Dottie first decided to run for office, she was rebuffed. “The Republican Party did not want me. They picked someone else, so my husband and I went out every night and went door-to-door,” she said. “We pushed hard and I beat my opponent, much to the dismay of the Republican Committee. Maybe I just stayed in the race to taunt the heck out of them.”

Dottie is a woman who knows where she belongs, and that place is Shelter Island. In her 82 years, she’s moved once, from the house on Midway Road where she grew up amid lima bean fields, to the home Fred Ogar built on Smith Street when they married in 1961.

Dottie was the third of four children of Albert Smith and Helen Dickerson Smith. “My family goes way back in history here,” she said. “A list of people who were town officials includes my uncle Otis Dickerson, who was a judge and a councilman, Ed Baldwin a Town Clerk, my mother was Town Clerk, and my grandfather Herb Dickerson was superintendent of highways.”

Dottie’s entire education took place at the Shelter Island School. “I didn’t attend kindergarten because they didn’t have kindergarten, that’s my excuse for everything.”

One of her teachers is still alive and living on the Island, the home economics instructor Jackie Tuttle. “When Jackie got out of college, this was the first school she taught in, and I was in her class,” Dottie said.

Her graduating class in 1956 included Kolina Nevel Reiter, Marge Card (who passed away recently) and former Town Supervisor Hoot Sherman. The class of 11 girls and 11 boys moved like a pack. “We all went to the movies in Greenport the same night, everyone went to the basketball games together, we were all one big group. It was a good class,” Dottie said.

Dottie didn’t go to college. “My brother just ahead of me went to college, my sister right behind me was going to college and my mother couldn’t afford it,” she said.

On Shelter Island in the 50s, everybody knew everybody. She and Fred started going together in December of 1955. “He had to go and do his stint in the army, and I made him build me a house,” she remembered. “He did a lot of it, and his friends would come over and help. You could do that in those days, people would just show up and do things, like put in a door.”

On Oct. 28, 1961 they married, and moved into the house on Smith Street.

Their daughter Sharon was born in 1963. “My one and only,” said Ogar. Sharon grew up on the Island, is now Sharon Jacobs, and has a daughter of her own, Mariah, who also grew up here. Sharon recently retired after over 13 years working beside her mother in the Town Clerk’s office.

For 10 years after graduating from high school, Dottie worked as a switchboard operator for NY Telephone in a building across from the Heights Post Office. In those days, switchboard operators manually connected calls from outside to the correct number on the Island.

“It was before 911 was invented, so we got all the emergency calls. One night they had the big fire in the Heights, involving two or three houses. That was quite a wild night in the office. The fire wasn’t too far away. You could lean out the window and see it.”

The job ended when the phone company brought in direct dial service on May 1, 1966.

After Helen Smith became Town Clerk in 1958, Dottie began working in the clerk’s office part time to assist her mother. There were no parking permits until 1966, and no mooring permits until 1987.

The work consisted of dock permits, sitting in on and recording meetings, and paying the bills. Dottie, who never expected to do office work, had not learned to type, so she was glad to be able to take an adult education typing class offered at the school.

In the spring of 1977, Helen Smith told her daughter she was ready to retire, and Dottie decided to run for the office her mother had held for almost two decades. “I told her I wasn’t sure I was that interested in it, because I didn’t know if the people wanted me,” she said.

But the people spoke in the fall of 1977, and have re-elected her to every term since, frequently unopposed.

Although her husband’s passion for antique cars is legendary, it’s an interest they both share. At car shows on the Island and nearby, the Ogar family is always there beside a meticulously-restored vehicle or two, and the annual Memorial Day parade often features an Ogar-restored car, driven by a trusted family member.

“We’ve never bought a new car,” Dottie said. “When we moved into this house, Fred had one of his old cars in the basement. People asked, how are you going to get it out of the basement? He took it apart and moved it with a backhoe.”

Of all the changes over the years in the way the Town operates, COVID has caused the biggest upheaval in Dottie’s opinion. “It was a whole different way to do our business — out the back window, we couldn’t let people in,” she said.

She recalls that when the Town was building an addition to the school house, they had classes in the church with lower grades going to school in the morning, and upper grades in the afternoon. “That was a very big change,” she said.

She’s heard the rancor and sniping in Town meetings, but pointed out that there has been strong disagreement in the past as well, usually around difficult issues such as affordable housing.

Dottie says the most interesting part of being town clerk is the history recorded in that office. The assessor’s books were copied every year to be sure they were legible, and the minutes go back to the 1700s in tall books on legal-size paper that include every town meeting and resolution.

“We are up to around 50 of those,” she said. “Take one of the old minute books that go way back to 1700 and start reading. You can get hooked on this.”

Lightning Round

Favorite place on Shelter Island? Where I’m sitting right now, a very old rocking chair given to us by the neighbors when we built this house.

Favorite place not on Shelter Island? I don’t have another favorite place.

When was the last time you were elated? When my granddaughter, Mariah, got engaged last summer. It was a great day when that happened.

What exasperates you? When people don’t get along the way they should.

When was the last time you were afraid? One night during a real bad storm, and my husband [a volunteer firefighter] went out because a house on Baldwin was struck by lightning and burned. My kids were here with me.

What is the best day of the year on Shelter Island? The car shows are a lot of fun.

Favorite movie or book? I don’t watch that many movies because I fall asleep. When my granddaughter was little I’d invite her over to watch a movie and she’d say ‘Why? Do you want to take a nap?’

Favorite food? Dark chocolate cake with seven-minute frosting. I make that for my birthday every year.

Favorite person, living or dead? My aunt, Katherine Dickerson Wilcox. If I had to stay with anybody, I would stay with her. She was the librarian for many years.