Paul Shepherd has lived on Shelter Island his entire adult life, but his early childhood in Missouri, the “Show Me State” left a mark on him.
Published in the Shelter Island Reporter on May 21, 2015
Paul Shepherd likes to question authority. He calls himself a non-conformist, a one-time rebel, and prior to his election to Shelter Island Town Board in 2011, an outspoken critic of local government. Since becoming one of four councilmen, who along with the Town Supervisor make up the Board, he respects his fellow lawmakers he said, but often disagrees with them. Publicly, and vociferously.
Born in West Plains, Missouri in 1955, Paul left as a kid, but is quick to give the “Show Me State” credit for his temperament. ”It really stuck,” he said. “Just the way I am. I take nothing for granted.”
Paul’s mother Edith left Missouri, and her husband, for Shelter Island around the time of Paul’s third birthday. “She did whatever she had to do to get free and to protect me,” Paul said. He grew up with his older brothers, Jim, who now lives in Muscatine, Iowa and Gene who still lives on Shelter Island. His younger sister, Edith passed away in 2014.
“My mother was a rebel as well. A single mother in the 50s,” Paul said. “She and I had a tempestuous relationship.” He went to the Shelter Island School until he hit the pre-teen years. Then Edith sent Paul to follow his brothers at Bob Jones Academy, a strict, religious, “socially restrictive” school in South Carolina known for establishing discipline in the unruly. His dorm room housed five boys, included a double bunk, a triple bunk, and a prayer captain.
“I did well my first couple of years,” Paul said, “ But being somewhat naturally rebellious, I became too challenging for them to retain, so they requested that I not join them again. I wasn’t crazy about the authoritarian nature of things.”
He finished high school on Shelter Island, spent a couple of years at Florida Southern University studying horticulture, and dropped out because, “I was wasting my time and my money.” He came home in 1973 to work in landscaping, and later made the switch to carpentering. “I learned as I went, more from some than from others,” he said.
For eight years he worked with general contractors building homes and additions. In 1988, he went solo, determined to get new business by word of mouth, rather than advertising, and not “be a big-shot,” he said, because “I figured they paid a terrible price in terms of government oversight.” Since then, he has had steady work as a carpenter, and continued solo.
“I’m a day to day person,” Paul said. “My mom had higher hopes for me.”
Edith Shepherd worked for the Town as secretary for the planning board for many years, and died in 2007. “She did not live to see me on Town Council, she would have liked that,” said Paul.
Growing up without a father in the picture, Paul said he learned to do things on his own. “That’s the kind of thing that yields some rebelliousness,” he said. “Nobody told me what to do.”
Appropriately for a man who takes a dim view of laws, his partner of 37 years has been Jean Lawless. “We’ve been not-married a lot longer than most people have been married,“ said Paul.
Jean and Paul met when, acting on “word of mouth at a bar,” he went to tryouts for a new production of the Shelter Island Players. Although they lived across the road from each other, they hadn’t really met until they were cast as Pierre and the Ragpicker in “The Madwoman of Chaillot.” Jean has two children, and four grandchildren, Desmond, Milo, Ophelia, and Dutch.
Paul remembers Shelter Island in the 60’s and 70’s as a place decidedly more forested, less developed and more blue-collar than today. “Wintertime was a serious business here,” he said. Scalloping and fishing was a livelihood for many men, and “there was no overpopulation of deer, because deer was dinner.”
There was, said Paul, a lot of drinking. He reeled off the names of some of the local “gin mills” open year round in the 70s; The Candlelight, The Harbor Inn, The Pub, The Dory, The Chequit. “I quit in 1990. The party was over and it was time to go home,” he said. “I was never, ever the one to leave the party first.”
By today’s standards said Paul, local enforcement of laws against drunk driving on “The Rock” in the 70’s was more relaxed. Today, the separation between law enforcement and the people they protect is greater, he said, partly because of litigation. “There is more of a divide now. The stakes are higher — if you let someone go [without a ticket] and they go on and hurt someone. I don’t say that it is wrong. But it is what happened.”
In 2009 Paul, still a steadfast questioner of authority, made an unsuccessful run for Town Supervisor, as the Local Liberties candidate, a party name he made up when officials in Riverhead insisted he list a party affiliation. Subsequently he mounted a successful bid for a Town Board seat in 2011. “I never wanted to be someone who makes laws, because I don’t care for them,” he said. “You really want power in the hands of people who don’t want it so much.”
Now that he has crossed over to the law-making side of local politics, Paul says his perspective has shifted a bit as well. “An informed opinion is sometimes a softer one. I still have to be part of it. Otherwise I would be isolated, and what is the point of that?” Referring to his four colleagues on the Town Board, he said, “I’m in a bit of a marriage with these people.”
Prior to his election to Town Board, Paul was a vocal critic of local government, often airing his opinions in letters printed in the Reporter. “ If I have been quiet of late it’s because I have a job to do. That’s one of vexing things about it.”
“I tend to speak my mind,” he said. “My mind is a free-range animal.”
Lightning Round- Paul Shepherd
What do you always have with you?
“My pens, so I can make notes if something comes up.”
Favorite place on Shelter Island?
“Sachem’s Woods It’s got a good feel. I walk through every other day with my dog.”
Favorite place not on Shelter Island?
“Any place is as good as another. I have not left New York in 15 years.”
“The Lord of the Rings Series. Tolkien had a strong sense of how to set up the battle between good and evil. I am always attracted to the underdog.”
“Chuck steak. Broiled or barbequed.”
Favorite person, living or dead, who is not a member of the family?
“It would not be appropriate to leave Jesus out the conversation.”