Island attorney Ron Rappaport, 74, dies unexpectedly

The community and his family are devastated by the loss.

Jane Kaplan and Ron Rappaport at a family celebration. —Courtesy Rappaport Family

The Island woke up to shocking news over the weekend that the prominent attorney and community leader Ronald H. Rappaport died unexpectedly on Friday night in Vineyard Haven. He was 74 years old, and lived year-round in Chilmark with his wife, Jane Kaplan.

Born and raised on Martha’s Vineyard, Rappaport lived an extraordinary life, serving as municipal attorney for five of the six Island towns and the Martha’s Vineyard Land Bank, and offering legal counsel and sound advice to a wide circle of friends, business owners, politicians, and celebrities from near and far. His father, Dr. David Rappaport, was an Island physician, and his mother, Adeline Rappaport, was a teacher, and also founded a notable Island travel agency. Rappaport grew up riding bicycles around Oak Bluffs and playing sports with the neighborhood kids. The Vineyard was truly his home. 

After graduating from Stanford University, Rappaport worked under former Massachusetts Sen. Ed Brooke in Washington, D.C., before enrolling in Boston College Law School. He was a partner at the Boston law firm Friedman and Atherton. In 1984, he returned to the Vineyard and founded the law firm Reynolds, Rappaport and Kaplan — now Reynolds, Rappaport, Kaplan and Hackney, the largest law firm on the Vineyard — with his wife and attorney Jim Reynolds, on Cooke Street in Edgartown. 

Jane Kaplan met Ron in 1975 when they were both taking a bar-review course after graduating from law school. The course was held in an enormous hall in Arlington where “you could cut the anxiety with a knife,” Kaplan told The Times. She had gone to law school out-of-state, and didn’t know many people taking the exam. Kaplan decided she’d opt to go to the evening, video-recorded version of the course, giving herself time for the beach that day.

Being a leftie and the desks being the old-fashioned L-shaped kind, Jane explained that she got another desk, and pulled it next to her so that she could take notes with her left hand. 

“I had some books, and I put them on the right … and I saw somebody out of the corner of my eye coming to sit there, and I was pissed,” Kaplan remembered with a little chuckle. “Then I looked, and it was Ron and he wasn’t like 99.9 percent of the other people there. He was relaxed, he had hair like you don’t even know, and he had a black Greek sailor’s hat on. As I’m rising up and seeing who this person is, I thought to myself, ‘Oh, this is interesting.’” Kaplan said she was shy and Ron wasn’t saying anything either, but then she chuckled at something in the video, and “he decided he liked my laugh and he started talking to me.” 

Kaplan and Rappaport were both trial lawyers, and were married for eight years before their daughter Julia arrived. Kaplan was working at a large firm, Hale and Dorr in Boston, and she said the pressure, commitment, and the time it involved was incredible. She took a yearlong leave of absence after Julia was born, and during that time, she and Ron decided to move to the Vineyard.

“I thought, I can’t be a mother and do this, so after ups and downs and ins and outs, we moved to the Vineyard,” Kaplan said. “Dennis daRosa had been Ron’s oldest friend, and Dennis said, ‘You should come to the Vineyard and you should open up the law firm.’” 

The couple had what Kaplan described as a “blind date” with Jim and Barbara Reynolds at the Homeport before deciding to open the Island law firm. She said when they first bought the building on Cooke Street, Ron was on the bottom floor with the receptionist, so that he could see everything that was going on, she was on the second floor, and Jim Reynolds was on the third floor, because he “didn’t want to see everything that was going on.” 

“He had the best judgment of anybody I know,” Jane Kaplan said of her husband. “He had an ability to get to the heart of a matter, and he was very, very creative. He had an amazing intellect, but he was governed by his heart.”

While Rappaport loved the Island, his family was everything to him. He especially enjoyed playing with Julia’s two young sons, 3½-year-old Sam, and Charlie, who had just turned 1. “He doted on my sons,” Julia told The Times. “He thought they were the most perfect thing. He said, ‘Jules, I think Sam is a genius. I think Sam is the most beautiful child …’” Julia said that Sam was riding a bike from a very early age, and her father couldn’t have been more proud, he himself being an active rider. Before long, Charlie came along, and Rappaport grew into an even more loving grandfather. 

“Dad could not have been prouder,” Julia said. “When Sam would get cranky, Dad would say, ‘Sam, let’s go look at the trucks.’ They would stand at the head of the road and watch all of the trucks go by. Then he’d come down to the house and say his arm was sore. I would tell him that he could’ve put him down, but he’d say, ‘No, I want to hold him.’” 

Julia told The Times that anyone with a good relationship with their parents thinks that theirs are the best, but that her father really was the best. “He was my biggest champion,” Julia said. “He answered the phone every time I called, and half the time it’d be, ‘Jules, I’m in a meeting and I can’t talk,’ and then I’d say, ‘Dad, why did you pick up?’ He was there for me. There was never a single time that I doubted he’d be there, and that goes for my mom as well.”

Rappaport was a loving father to Julia, she said, leaving work early to take her sledding at Mink Meadows on snow days because she was afraid of the much larger hill at Tashmoo. The advice Rappaport shared at home was just as valuable as the advice he gave his many Island friends and colleagues. 

“He gave the best advice,” Julia said. “One story I was thinking about is tugging at my heart so much. People think of him as being so tough and practical, but at his essence he was love — just love. He loved love.”

Julia explained that when she was going through a rough time with a previous relationship before she met her husband, her heart was shattered, and she drove home to the Vineyard to be with her parents. (They had always told her that if she falls down, she can always come home and they would be there to catch her and help her back up.) 

“I’m crying, I’m in my early 30s, and I asked Dad what should I do,” Julia remembers. They took a long walk on the beach together, and her dad told her, “All I know is if I was your partner, I would have followed you, and if you told me not to come, I would have come anyway, and if he didn’t come, he does not deserve you.”

Julia said that she was not one of those people who wished she had told her father something before he died, because they had always said whatever they needed to say to each other. “I’m at peace, because I know without question that we said everything — and we always did,” Julia said. “But my world will never be the same.”

A number of Islanders took time to reflect on what Rappaport meant to them, and how his passing will impact the community. Most of them see the beloved Island native as “irreplaceable.” Rappaport provided public service through numerous capacities, including as the Vineyard’s Steamship Authority governor, and he was chairman of the board of the Martha’s Vineyard Bank Charitable Foundation.

“His wisdom and knowledge was instrumental in nearly every facet of this Island,” Tom Murphy, Aquinnah select board member, said. “He was one of the very few people everybody loved.”

People from all over the Island and beyond report that Rappaport was kind and generous with his time and with his legal advice, with many commenting online about how he made others feel comfortable no matter the situation. 

Edgartown town administrator James Hagerty echoed the common sentiment that Rappaport was able to talk to anyone, no matter who they were. Hagerty worked with Rappaport both in his role for the town and as a member of the MV Bank’s Charitable Foundation board. When Ron spoke, people listened, whether in a boardroom or on the floor of a town meeting. He always represented the best interests of the Island, and could effectively convey his sage guidance to anyone, regardless of their background,” Hagerty wrote in an email to The Times. 

“He left a wonderful legacy that we are all grateful for,” Gail Barmakian, Oak Bluffs select board chair, said. Barmakian also told The Times Oak Bluffs was “privileged and lucky” to have had Rappaport as legal counsel to the town for decades. 

“Not only was he town counsel, but he was an Islander,” Mark Leonard, Oak Bluffs select board member, said. 

For a number of Island leaders, Rappaport was also a cherished friend. 

“He was the most compassionate and empathetic, wise counsel that I’ve dealt with here, and I will miss him,” Jeffrey Madison, Aquinnah town administrator, said. Madison told The Times he had been friends with Rappaport for 50 years, recalling he had just met Rappaport on Thursday to talk about town business: “I will miss him terribly.”

Denise Schepici, president of Martha’s Vineyard Hospital, where Rappaport served on the board of trustees, issued a statement last Saturday: “We are deeply saddened by the loss of Ronald Rappaport, an iconic figure who served as a member of the Martha’s Vineyard Hospital board of trustees. More importantly, he was a cherished friend and confidant. Our sincere condolences go out to his family, friends, and the many individuals whose lives he touched with his dedicated service to Martha’s Vineyard.”

Rappaport is survived by his wife, Jane Kaplan; daughter, Julia Rappaport of Newton and Chilmark, her husband Jack Spencer, and their two sons, Sam and Charlie; and by his brother, Alan Rappaport and his wife Jill Rappaport, and a sister, Susan Cohen and her husband Fredric Cohen; as well as many beloved nieces and nephews, and a great-nephew. A public celebration of his life is being planned for a future date. 


  1. Please report on his memorial service date and time and place as soon as possible… it should be held at the Tabernacle in his hometown where the throngs the community that will turn out can spill out onto the grass… thanks

  2. What a truly lovely photograph of Ron and Jane. Thank you, Rappaport family, for sharing it with us.

  3. I had many interactions with Ron over the years, initially in my capacity as an attorney, and subsequently working collaboratively with him on different community boards. Ron was a dedicated servant to, and advocate for, this entire community, and he worked tirelessly on our behalf in a wide range of endeavors, to which he unfailingly brought great judgment, intelligence and perspective, as well as great talent for getting things accomplished. In particular, his involvement in helping organize and drive the MVYouth program forward has been a key factor in its success, and I know the impact of that particular charitable program gave him great satisfaction. I often marveled at his ability to juggle so many disparate responsibilities simultaneously, and yet he was always in control and on top of everything. On a personal level, despite his many accolades and accomplishments, at his core he was seemingly just a regular guy who, in addition to his adroit intellectual skills, was blessed with a great sense of humor and a very kind and compassionate heart. I found numerous reasons to like and admire him.
    We were very fortunate to have Ron amongst us for as long as we did. He was one of those generational leaders who emerge perhaps once every generation if the community is so lucky, and it will likely be many years before we are blessed with another like him in our midst. He was truly a rare bird, and I will miss him dearly.

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