Island attorney Ron Rappaport, 74, dies unexpectedly

Leaders from Vineyard towns say they are shocked and devastated by the loss.

Ron Rappaport suddenly passed away on Friday. —MV Times

Updated 6:52 pm

The Island woke up to shocking news today 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.

“I’m shocked and I’m devastated. This is a huge loss for the town of Chilmark, for his family, for his friends … and for the entire Island,” Jim Malkin, Chilmark select board chair, said. Malkin told The Times Rappaport had mentored him when he was moving onto the Vineyard as a “washashore” in 2010. 

Born and raised on Martha’s Vineyard, Rappaport lived an extraordinary life, serving as an attorney for five of the six towns on the Island and offering legal counsel and sound advice to a wide circle of friends, business owners, politicians, and celebrities from near and far.

After graduating from Stanford University, Rappaport worked under former Massachusetts Senator Ed Brooke  in Washington, D.C., before enrolling in Boston College law school. He met Kaplan while studying for the bar exam. 

Rappaport was a partner at the Boston law firm Friedman and Atherton. In 1986, he returned to the Vineyard and founded the law firm Reynolds, Rappaport, Kaplan & Hackney — now the largest law firm on the Vineyard — with his wife and attorney Jim Reynolds on Cooke Street in Edgartown. 

Multiple Vineyard leaders told The Times on Saturday what a terrible blow Rappaport’s passing is for the Island. 

“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.”

“Fortunately, he was able to love his life and live in this community,” Juli Vanderhoop, Aquinnah select board member, said. She told The Times Rappaport had “done so much” for the Island and was someone who was a staunch member of the Vineyard community.

“Ron Rappaport was an Island treasure and his loss is going to be felt by all of us,” Roy Cutrer, Tisbury select board chair, told 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  the legal counsel for the town for decades. 

The Rev. Charlotte Wright of the Chilmark Community Church wrote that Rappaport was part of the legal team that represented the church in its land court litigation. “We would not have exited from the UMC successfully without him,” Wright wrote in an email. “He referred to us as ‘my little church.’ We will be eternally grateful for his dedication to the Island and beyond, and his love for this church that he considered his own.”

As a trial attorney, Rappaport also led some high profile court cases.

In 1997, he represented Edgartown in a landmark court decision in which the Massachusetts Supreme Judicial Court upheld three-acre zoning in the town. This was the largest minimum acreage requirement ever allowed in the state. 

“A developer wanted to reduce the three-acre zoning and put in a lot of units out on the south shore of Edgartown, where the ponds are,” Rappaport previously told the Times. “And we argued that the ponds are environmentally fragile, and what’s more, they’re a big part of what makes the Vineyard the Vineyard, and we won. And that case has had consequences all across the state.”

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

Leonard recalled seeing Rappaport speaking during the dedication ceremony for a plaque in memory of Dennis daRosa, a founder of the Oak Bluffs Association, on May 26. He said it was evident Rappaport was a great man and he was beloved by the community. 

“It’s just sad to see our long-term residents passing on,” Leonard 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.”

“Ron Rappaport was a remarkable person and a dear friend whose impact on Martha’s Vineyard is immeasurable,” Cynthia Mitchell, West Tisbury select board vice chair, told The Times in a text. “There was simply no one like him. His contributions to local politics and community philanthropy were unparalleled. As his friend, I know that what made Ron so special was about much more — he loved people and he made life better for anyone lucky to have known him. He will be deeply missed in nearly every corner of public life on the Island. It seems impossible to imagine the Vineyard without him.”

Rappaport provided public service through numerous capacities, including as the Vineyard Steamship Authority governor and was chairman of the board at the Martha’s Vineyard Bank. His father was a well-known Island physician, and Ronald was born on the Island and came of age in Oak Bluffs.

“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,” Denise Schepici, president of Martha’s Vineyard Hospital, said in a statement issued on Saturday. “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 was a dedicated cyclist and could be seen riding his bike up-Island just about every day in the summer and fall. But those who knew him well say his greatest dedication of all was to his family. 

“One of the best sights in Chilmark recently has been driving along South Road and going by Ron’s driveway as he held his baby grandson, delightedly watching the trucks go by,” Malkin told The Times. 

Rappaport is survived by his wife Jane Kaplan, daughter Julia Rappaport of Newton and Chilmark and her husband Jack Spencer and their two sons Sam and Charlie; and by his brother, Alan Rappaport, and a sister Susan Cohen, as well as many beloved nieces and nephews and a great-nephew.


  1. We have lost our North Star to which all things were measured: brilliance, friendship, humor, loyalty and heart. There is not one piece of the island that Ron’s light failed to touch in some way. His legacy has been forever embedded in this island, and in all who were blessed to know him.

  2. Truly a shock. What an incredible loss. Our thoughts are very much with you, Jane and Julia.

  3. Ron’s passing is a monumental loss to the island
    He will never be matched or replaced
    Let’s just see what happens going forward
    RIP Ron,
    and thank you for your unrelenting dedication to the island
    Til”we meet again

  4. Ron showed up at every event to pay his respects. If someone was retiring or had passed away, there was Ron, dropping in to say a heart felt thank you or to offer his condolences. You could ask him anything at all and he would always provide sound advise, never making you feel inferior. He was respectful and kind and he had a great laugh. Ron will be deeply missed.

    • Ron graciously came to my retirement party at the West Tisbury Library a week ago Friday. My last view of him was outside the library as he was leaving and he greeted Janice Haynes who Jeremiah had brought to see me but who was too weak to come in to the event. That is my mind’s last image of both of them. I am so heart broken to lose both within a week after. And, may I add, that they both competed for “best hair on island.” Miss them both, so much, already.

  5. I remember well that he came at the last minute to a small farewell celebration for Linda Marinelli, as she left the Island and Oak Bluffs, to which she was devoted. In their political lives she and Ron often were opposed. He was very complimentary to her, and she was very flattered. Everyone on the Island will miss Ron Rappaport. May his memory be a blessing.

  6. Oh my!! Such an unbelievable human being! Such a loss to the Island and, of course, to his family. Another brilliant, special Islander that will never be replaceable. Will miss seeing him on the rec paths also.

  7. When my wife, Karen, passed away in 2005, I needed some legal help to try and figure out some complex insurance issues. I needed an attorney who could do some digging for me. Ron listened to me, and we got to work. I got a bill eventually, for something like five thousand dollars, but Ron assured me that he just needed to prepare an invoice – but that there was no need to pay that amount. The work was basically done for free. What a great man. He will be deeply missed.

  8. This was a complete man who made you feel at ease in any situation. It was a great gift he had and one that helped so many in good and trouble times. Ron I hope your ride is a fast won with no traffic in front.

  9. Thank you, Ron, for being an amazing human being! Thank you for your love and compassion for our community and your family, your attentiveness (especially to those in need), your compassion, generosity, your smile, and of course, your wild hair! May you rest in everlasting peace, Ron. The Vineyard will never be the same without you.

  10. Ron Rappaport was a cornerstone of the island community. He was good friends with my step brother-in-law who spoke very highly of him.
    This is a significant loss to the island community. I did not realize Ron Rappaport was born and raised on Martha’s Vineyard.9 I just knew that he loved the island and the island loved him. Thanks for all your dedicated years of kind service Ron. My condolences to your family and friends and all the people who loved you and will miss you.

  11. Cindy daRosa Barrett
    Ron was such a wonderful person to all. As my brother Dennis close friend – they grew up together in Oak Bluffs. Many times Ron would be at our home or Dennis at his familys home. A very close true friends; as they were throughtout thei entire life. Ron was a friend and major part to the Island and to almost every person on the Island. My sincere sympathy the his family and to all who knew Ron. He will be remembered forever.

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