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Remembering the many roles of Jim Dougherty’s life: The former supervisor’s last interview

When Jim Dougherty entered stage right as the Mayor of Liverpool in “Lords of Menantic,” last month, and delivered a proclamation of thanks, there wasn’t a dry eye backstage, and not just because the man was a champion of land preservation on Shelter Island, served as town supervisor from 2008 through 2017, and had just been released from the hospital.

His life since leaving office was full and productive, but in 2021 he was cast in a new role, Elliott in Lisa Shaw’s community musical “Hill of Beans.” In 2022, he agreed to perform in “The Prospect of Summer,” and last month in the “Lords of Menantic,” he played the mayor with a pomposity and exuberance that belied his years-long battle with illness that ended last week. 

I’ve interviewed him many times over the years, but it was not until working side by side on the community musicals that I got to know him. Our last interview was on August 3 in the peace and beauty of the garden that surrounds his home, a place of refuge and rejuvenation for him. Jim passed away on Saturday, Aug. 19, 2023 at the age of 86.

The family will receive friends on Wednesday, August 23, from 4 to 7 p.m. at the Community Center on School Street, Shelter Island.

The Shelter Island Funeral Home is serving the family.

Shelter Island became a second home for Jim and his wife Nancy when they bought a house in 1976 at the highest point of Ram Island Road facing Gardiners Bay. The modest, comfortable home was owned by the Tuttle family for its first hundred years. The couple began to live there year-round in the 1990s, and although Jim kept their home in Gramercy Park, and even built a new home on the south side of Shelter Island this year, he never left the house on Tuttle Hill.

The Doughertys raised Jim’s brother’s son Terence. Jim was extraordinarily proud of his nephew’s accomplishments, which included graduating from Columbia Law School, and becoming deputy executive director for operations and general counsel of the ACLU.

Jim started his working life as a lawyer on Wall Street working for “a white shoe firm” (a term describing prestigious, long-established firms), where he learned the arts of negotiating and reaching agreement and became known as “Deals” Dougherty. He went on to Pathmark Supermarkets where his star rose quickly and steadily until he ran the place.

“That was my most satisfying career because I was very successful,” Jim said. “Being supervisor wasn’t the job I enjoyed the most, but it was 10 wonderful years.”

The American Legion and the Youth Center

Jim demonstrated his style as supervisor in April of his first year in office when he engineered a deal that kept the American Legion in their building, and made room for a youth center upstairs at minimal taxpayer expense.

“The American Legion came to me and said they were giving up Legion Hall,” Jim said. “There was a big public hearing about the taxpayers bailing out the Legion, and I kept saying, ‘It ain’t going to happen.’  I went to see them and said ‘I’ll give you a dollar for the building and a perpetual lease for the basement.’ That was the deal, and they got me to sign the dollar and hung it up in the Legion for about five years until a hard-bitten Republican tore it down.”

A Legacy of Land Preservation

It was Jim’s opinion that the work he did to preserve undeveloped land on Shelter Island when he was chairman of the Community Preservation Advisory Board and during his terms as supervisor helped preserve the essential character of the Island.

“I think we’ve done a good solid preservation job, “ he said. “A lot of people were a little skeptical when I first came in because they thought it would increase taxes. It didn’t. We increased real estate values and kept the population stable.”

Jim spearheaded the effort to pass a 2% tax on real estate transfers and create the Community Preservation Fund in 1998. The measure passed in a five-town referendum. He was then asked to head the committee to identify and preserve the land, and he did it for nine years before being elected supervisor. “I had no power, I could just recommend,” he remembered. “I had tremendous luck.” 

Working with just eight or nine landowners on Shelter Island, Jim’s committee put together deals that resulted in about 300 acres of preserved land, including Klenawicus Field, Burns Road, and the Mildred Flower Hird Preserve. Each deal was complex, and usually involved dealing with more than one family member, as well as land preservation partners from Peconic Land Trust, Dering Harbor Village and Suffolk County.

“I think you are in office to get something done. And if you don’t get something done, it’s all talk. The idea is to get from A to B. I found out early on when I was a lawyer on Wall Street, that perfection drives out the good. You have to go for the good.”

The issues facing the Island today

Out of office in 2018, Jim remained an interested, and occasionally vocal, observer of local issues. He said that the characteristics of local officials have changed. “I detect a little more self-absorption,” he said. Some of our leaders now are more concerned about promoting and progressing themselves than helping out the Island.” 

Jim’s campaign slogan more than once was the mantra, “Ticks, Taxes and the Aquifer,” a set of issues that he considered still important, albeit with different emphasis. “Taxes always will be important with everyone,” he said, “and it’s still a sole-source aquifer, and we are responsible for it. If we poison that pool of water we’re finished. “

He opposed allowing Gardiner’s Bay Country Club to use more water. “Golf is a recreational sport,” he said. “If part of the fairway is brown, use a different club.” He felt that land preservation has slowed in recent years, and it’s a shame. “Development is still a primary issue,” he said. “There are a lot of developers over in the Hamptons who are drooling over Shelter Island.”

Dougherty’s Last Great Campaign

Jim’s wife Nancy, an accomplished writer and recipient of the 1987 PEN Girard Award, died in 2013 from early-onset Alzheimer’s disease, which came on in her 50s. For years before she became ill, she was under contract with Knopf for a biography and was close to finishing when she became too ill to continue. Her original editor had died, and after Nancy’s death, the publisher decided against going forward without an author to see it through the editorial process and promote it.

Another complicating factor was the subject of the book, Reinhard Heydrich, a Nazi official who became head of the Gestapo and who Hitler referred to as the man with the iron heart. Although Nancy’s portrayal of Heydrich was not sympathetic, her major source was Lena, Heydrich’s wife, who survived her husband by four decades, and tried to shape his biography.

For an orphaned book without editor or author to be published is unusual, to say the least. But for an orphaned book with a problematic subject to be published and be critically well-received is a transcendent miracle.

A turning point came when Jim was able to interest the journalist and former New York Times Book Review Editor Christopher Lehmann-Haupt in Nancy’s unpublished manuscript.  The interest turned to near-obsession, and Jim hired Mr. Lehmann-Haupt to complete the book. “The editor at Knopf had told me, you’re wasting your money, go to hell,” he said. “When I got Christopher Lehmann Haupt involved, she said, ‘We’ll publish it.’” 

Mr. Lehmann-Haupt finished the manuscript, wrote a foreword and died of a stroke a few days after visiting Jim on Shelter Island, leaving the book orphaned again. Jim hired editors to complete the work of documenting sources and securing permissions.

Last year, “The Hangman and His Wife: The Life and Death of Reinhard Heydrich,” by Nancy Dougherty, was published by Knopf and received notices and reviews in The New York Times, The New York Review of Books and The New Yorker.

Jim said in the years following his wife’s death, seeing her book in print was his primary reason for fighting to overcome his own serious health problems.

“Since Nancy’s death, really, my major reason for staying alive was to get her book published,” he said. “When it came out last February I was so happy. I fought hard for that and I don’t regret a moment.”