Ronald H. Rappaport, the respected and ubiquitous Martha’s Vineyard attorney whose work and relationships cut across nearly every aspect of Island life, died unexpectedly on June 7 in Vineyard Haven. He was 74 and had lived year-round in Chilmark with his wife of nearly 47 years Jane Kaplan.     

With his signature wiry, wild hair, Mr. Rappaport cut an unforgettable figure and occupied an equally unique role on the Vineyard over many decades. Outgoing and full of fun, he was also a fiercely effective negotiator who worked behind the scenes in myriad ways to resolve problems and advance community goals.     

He was a trusted municipal attorney who represented the towns in legal battles large and small and was a highly regarded presence in courtrooms from Edgartown to Boston. His friendships — both on and off the Island — were legion, and there were hundreds, if not thousands, who relied on him for his thoughtful counsel and advice. He wore an array of civic hats, among other things serving as the Vineyard Steamship Authority governor for seven and a half years in the late 1990s.     

Above all, he was deeply devoted to his family and always stayed true to his Island roots, understood the community values and way of life that are a hallmark of the Vineyard and fought to protect them.     

“We are a community of volunteers. We have to take care of ourselves,” he said during a 2000 ceremony when he was presented with the Hospice Spirit of the Vineyard award.     

It was a credo he lived by.     

Ronald Hall Rappaport was born on June 16, 1949 at the Martha’s Vineyard Cottage Hospital in Oak Bluffs, the second child of Dr. David Rappaport and Adeline Hall Rappaport. A revered Island physician, Dr. Rappaport had his office on Circuit avenue. Adeline Rappaport founded and ran a successful travel agency.     

He attended the Oak Bluffs School and played baseball in Viera Park, today still a home field for Little League on the Vineyard.     

In a 2020 commentary for the Gazette following the death of his lifelong friend Dennis daRosa, he vividly recalled growing up in Oak Bluffs in the 1950s and 60s.     

“We both appreciated how lucky we were to be from Oak Bluffs. We were close to our parents and our families, and we looked up to the parents of other neighborhood children. It was the best of small-town America,” Mr. Rappaport wrote. “Dennis and I would ride our bikes to school in the morning, then ride them home again for lunch .... When we got our report cards, Dennis and I would go to Our Market and Amos Sylvia would reward us with Fudgsicles.”     

He graduated from the Middlesex School in 1967 and Stanford University in 1971. After college he went to work for Sen. Edward Brooke in Washington DC. The Brooke family had a summer home in Oak Bluffs that stood about a center fielder’s throw from Viera Park.     

He had known since childhood that he wanted to be a lawyer, but his path to law school was unconventional.     

While he was working in Washington for Senator Brooke, he got a call from a person he knew who had recently taken a job as a professor at Boston College Law School, according to his wife, Jane Kaplan. Though the fall semester had already begun, the friend said the school had fewer students than expected.     

“They had spaces, and he said if you want to come up right now you could be a first-year student. He never took the LSATs, he never applied,” Ms. Kaplan said.     

He enrolled at BC — and simultaneously ran the Boston campaign office for Senator Brooke who was running for re-election — graduating in 1975. He and Jane met at a post-graduate summer course as they both prepared to take the bar exam.     

They married in 1977. Both became lawyers at respected Boston law firms; a shared love of the Red Sox and travel that would continue throughout their long marriage.     

Soon after their daughter Julia was born in 1984, finding the demands of working at high-octane law firms did not fit well with family life, they moved to the Vineyard.     

“We decided we would try to create our own law firm, where we could set our own hours,” Mr. Rappaport recalled in a 2016 Gazette interview with his longtime partner Jim Reynolds.     

The firm of Reynolds Rappaport and Kaplan (today Reynolds Rappaport Kaplan and Hackney) was born.     

“I thought it was going to be more of a boring, mundane, legal practice with more family time,” Mr. Rappaport recalled. “The surprise has been our cases have been complicated, interesting, fascinating, stimulating. Frankly, I’ve worked just as hard here as I did in Boston. The idea of getting more family time didn’t really work out the way I envisioned it.”     

His daughter Julia had a different take. “He made a conscious choice to come to the Vineyard and do what his father did — it was more than just a move and starting a law firm, it was something different,” she said. “The Island was his family — if you were family, he took care of you.”     

She recalled one year when she was home from school for Christmas break. “Very early on Christmas morning there was a knock on the front door. Everyone was sleeping. I went down and opened the door and a man was standing there — he said not a word, just handed me a bag of scallops.”     

It was a Menemsha fisherman’s recompense for legal work Mr. Rappaport had done for him.   

 His first town counsel job was with the tiny town of Aquinnah (then Gay Head). Eventually he would become counsel to five of the six Island towns and the Martha’s Vineyard Land Bank.     

In one of his many cases, he represented Edgartown in a decade-long fight to preserve Herring Creek Farm from development, resulting in a landmark 1996 Supreme Court decision upholding three-acre zoning. “Edgartown and the other communities on the Vineyard will stand and fight to protect our environment against anyone, no matter how well financed, aggressive or obnoxious,” he said at the time.     

There were battles too during his years as SSA governor, when powerful state legislators from New Bedford pressed for the state to take control of the quasi-public boat line.     

At the Hospice event in 2000 Mr. Rappaport was lauded for his work representing the Island during a turbulent period for the two Islands.     

“I never wanted this to be my identity,” he bluntly told the gathering. He continued: “Freight service to New Bedford is not about whether it is a six-month or an eight-month, or a one or two-year program. It is about control. This is about who is going to decide how many cars there will be, when they will run and whether there will be a late night boat for the hockey team. We are looking at this as a lifeline.”     

Carol Borer, the late executive director of the Martha’s Vineyard Commission, added her own perspective.   

 “I believe you are the Vineyard’s lifeline,” she said.     

Mr. Rappaport doted on his two young grandsons, loved the beach and was a familiar presence on up-Island roads on his bike, his unruly hair spilling out from beneath the helmet. He had planned to retire soon. His sudden death left the close-knit Vineyard community in shock on a brilliant June weekend. An outpouring of comments on the Gazette website recalled his humor, thoughtfulness and countless contributions to the Island. It called to mind his own remarks 24 years ago at the Hospice event.     

“There is a downside to public service; it is that you can only hold the banner so long,” he said. “Others have to step up to these leadership positions.”     

He is survived by his wife Jane Kaplan of Chilmark; daughter Julia Rappaport of Newton and Chilmark and her husband Jack Spencer; two grandsons who were the joy of his life, Sam Haven Rappaport Spencer and Charlie West Rappaport Spencer; his brother Alan Rappaport of Chilmark and Florida and sister Susan Cohen of Newton and their spouses Jill Rappaport and Fredrick Cohen; nephew Alex Rappaport and his wife Catalina of New York, niece Hilary Rappaport and her wife Lindsay of New York, nephew Michael Cohen and his wife Mara Green of Newton and Tisbury, and niece Cindi Samuels and her husband Greg of Chagrin Falls, Ohio. He is also survived by grand nieces and grand nephews, all of whom he took pride in: Harper and Reese Cohen, Emilee and Roxie Samuels, Lyle Rappaport and a new grand niece that will join the family in several months.     

A public memorial is being planned for late summer.