The Agricultural Hall in West Tisbury was standing-room only on Saturday afternoon as the Island celebrated the life of Ronald H. Rappaport, who died suddenly in June 2024.
Mr. Rappaport was remembered passionately by family, friends, co-workers and neighbors for a life dedicated to preserving and nurturing the Island’s character.
Laughter accompanied tears as many spoke about Mr. Rappaport’s accomplishments, his deep love for the Vineyard community and his signature hairstyle.
“It’s exactly the type of gathering that Ron would have relished, working this crowd, connecting, laughing and making us all feel special,” said Ron’s brother Alan Rappaport.
A fierce lawyer and social butterfly, Mr. Rappaport was a regular sight on his morning commute, riding his bike from his home in Chilmark to his office in Edgartown, where the law firm he founded in 1986 with his wife Jane Kaplan and fellow lawyer Jim Reynolds was located.
Alan Rappaport compared his brother’s leadership to a cycling technique called drafting, where bikers ride closely behind one another to reduce wind resistance.
“We all drafted behind Ron,” Alan said. “His leadership kept us focused on the Vineyard... He made us a better community [and] it was quite a ride.”
Mr. Rappaport’s firm represents five of the six Island towns, and over the decades he won numerous cases defending the Vineyard against off-Island developers, often backed by large corporate law firms.
“He could have been a successful lawyer in any big city law firm, but he chose to move back to the Island, back to his roots,” said Kerry Alley, Mr. Rappaport’s friend from childhood.
He represented the town of Edgartown in a landmark decision where the Supreme Judicial Court upheld three-acre zoning at Herring Creek Farm, helping to preserve the fragile resources of the Great Plains of Katama.
Mr. Rappaport also convinced the Supreme Judicial Court to uphold a decision for the town of Aquinnah to prevent a large subdivision off Moshup trail, preserving yet another rare coastal habitat.
Isabelle Lew, who knew Mr. Rappaport since she was a child and worked beside him at his law firm since 2016, said the list of important court cases goes on and on. She said he was the Vineyard’s greatest guardian.
“At every turn, Ron was fighting to protect the Island, and in many ways it is Ron who we have to thank for the beautiful Island we know and enjoy,” Ms. Lew said.
Fain Hackney, a partner at Mr. Rappaport’s firm, said Ron was always the first in the office and the last to leave. He said Mr. Rappaport had unbelievable judgment, could explain complex subjects in layman’s terms and was most energized by his love for people.
“He was the closest thing to a mayor this Island ever had,” Mr. Hackney said. Jim Swartz, who co-founded MV Youth and led the establishment of the YMCA, said Mr. Rappaport was adept at identifying potential conflicts and resolving them before they even surfaced.
James Anthony, the president and CEO of Martha’s Vineyard Bank, echoed Mr. Swartz, describing Mr. Rappaport as a steady force when waters were rocky.
“His sharp intellect and confidence gave others the sense of safety, a sense of calm,” Mr. Anthony said.
Stephanie daRosa, whose father Dennis daRosa was Mr. Rappaport’s oldest friend, read a poem by Maya Angelou titled When Great Trees Fall, and shared how her dad and Mr. Rappaport showed her the importance of tradition and holding loved ones close.
“My Dad and Ron’s friendship taught me about family loyalty, community and most importantly, true friendship,” Ms. daRosa said. “Their camaraderie, compassion, endless stories and laughter shaped who I am.”
Peter Chernin, a friend of Mr. Rappaport’s for over 30 years, said he was the embodiment of what makes the Martha’s Vineyard community so special.
“We have all been so blessed to have Ron in our lives, and we pledge to nurture and protect this Island and this community,” Mr. Chernin said.
Mary Kenworth, who owns State Road and Beach Road Restaurants with her husband Jackson, said he was the life of the party. He would often call her to give a pre-game rundown of the events he had scheduled for the week, and then call again in the morning to debrief her about the dinner parties he loved.
“This seems like the moment I should say, I hope you rest in peace, but I’m not sure I do,” Ms. Kenworth said, speaking directly to Mr. Rappaport. “I think maybe I hope that you live it up in the afterlife and keep the party going.”
After Ms. Kenworth’s speech, the power went out for a few seconds, as if Mr. Rappaport was confirming he was having a good time wherever he was.
“That’s the second time that’s happened when someone’s been talking about Dad in public settings,” said Julia Rappaport, Ron’s daughter,
“We get it,” she said to her dad, looking up.
Julia Rappaport said that although many saw her father as a parent figure in their lives, as his only child she truly knew him as a father.
She shared memories throughout her life, including when she was a child and he would let her scramble out of the car and onto the roof as he sped down dirt roads and over potholes with a devilish grin. In the winter they would go sledding at Mink Meadows golf course, and in the summer he would instruct her how to dive under or jump over waves at the beach.
“Loss can be so lonely but being reminded that my family is carrying Dad on, that so many of you are carrying Dad on in your hearts, makes it a little less so,” Ms. Rappaport said.
Ms. Rappaport’s speech was followed by a poem written and read by Steve Ewing, titled Oak Bluffs Boy-Island Man.
“His sage advice / that served us once / in future will it gift us twice / For all his life for Vineyards / sake / his legacy is the bow wake / Bless you Ron / our honest friend / forever will you steer again.”
Alan Rappaport returned to the microphone to close the ceremony by telling the crowd that a Ronald H. Rappaport Scholar Fund had been created in partnership with the Martha’s Vineyard Bank Charitable Foundation, and that $1.5 million had already been raised by 200 supporters.
He then led the crowd in calling out one of his brother's lesser-known nicknames, Rondo. Everyone responded with gusto, shouting "Rrroonnddoo!" until the rafters of the Ag Hall nearly shook.
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