Ron Rappaport, the prominent local attorney and Island native who passed away unexpectedly last summer at the age of 74, was remembered by hundreds of Vineyarders and nearly a dozen speakers at a celebration of his life at the Agricultural Hall on Saturday.
Family, friends, and colleagues described Rappaport as “the closest thing to a mayor this Island will ever have,” a “wizard,” and an “Oak Bluffs Boy, an Island Man.”
Rappaport, born in 1949 in Oak Bluffs, was raised in the down-Island town by David Rappaport, a local doctor, and Adeline Hall Rappaport, who ran a travel agency. He graduated from the Middlesex School in 1967 and from Stanford University in 1971, going on to work for former Massachusetts Senator Ed Brooke in Washington, D.C. Rappaport then attended Boston College law school, and he met his future wife and colleague Jane D. Kaplan in a bar review course.
Rappaport spent his decades-long legal career serving the Island community, starting the firm now known as Reynolds, Rappaport, Kaplan & Hackney in 1986 alongside Kaplan and James F. Reynolds. With Rappaport, it won a number of landmark and high-stakes cases against off-Island developers and powerful legal teams, earning Rappaport and his firm a reputation as formidable defenders of Martha’s Vineyard against outside real estate interests. The law firm, now the Island’s largest, represents five of six Vineyard towns.
Speakers on Saturday remembered Rappaport as a caring and intelligent man who possessed a unique energy and outgoingness, and a unique look — two big tufts of scribble-like hair that often stuck out from the sides of his head.
Alan Rappaport, Ron’s brother, spoke first to the standing-room-only audience at the Ag Hall. Attendees unable to find seating lined up against the back wall, with dozens crowded under doorways. Alan spoke to his brother’s extensive reach within the Vineyard community, challenging himself to list the many local organizations Ron had been involved with.
“I tried to put together a list of all the places where he made an important difference,” he said. “But that list kept going, and growing. The towns, the local commissions, the Steamship Authority, the hospital, the Land Bank, Sheriff’s Meadow, MV Youth, Harbor Homes, Martha’s Vineyard Bank, State Road Restaurant, the response to COVID, Community Services, the scholarship to the Community Foundation, and that’s just the beginning of the list.”
Ron’s impact on those institutions, Alan said, can be described aptly with a biking analogy, as his brother was an avid cyclist and a memorable sight on Island roads.
“In biking there is a concept known as drafting … ” Alan said. “There is a lead biker and then those that follow. And based on the physics of airflow, those that follow the leader go 30 percent faster than they would have otherwise.”
Kerry Alley, who has known the Rappaport family since he was a child, when Dr. Rappaport removed his appendix, spoke to Ron’s dedication to the Island community and gifts as a networker and organizer.
“He could’ve been very successful in any big-city law firm,” Alley said. “But he chose to come back to the Vineyard, back to his roots.”
Alley highlighted one call that he made to Rappaport on behalf of the Red Stocking Fund, which has provided clothing, supplies, and toys to Island children at Christmastime for nearly a century. “A few years ago, we were on shaky financial grounds,” Alley said. “So I called Ron to see if he could be of any help. And without missing a beat, he said, ‘Let me see what I can do. I might find you a couple thousand dollars.’ Within two weeks, he had raised $100,000, which totally covered our budget that year.”
“That year, he truly was the mensch who saved Christmas,” Alley said.
Isabelle Lew, who has known Rappaport since her childhood, described him as a “creative, brilliant, and relentless” man who fought tirelessly to protect his Island home.
Lew told stories of Rappaport in action, one that she witnessed in person while clerking at the state’s Supreme Judicial Court. Rappaport stood out in more ways than one while making his winning arguments, she said.
“Who but the wizard appears to argue a pivotal land use case on behalf of the town of Aquinnah?” she said. “With the justices in their black formal robes, Ron gets up, looks over at me, and suddenly smiles with a twinkle in his eye. The wizard begins his argument and calmly, clearly and intelligently persuades the high court of Massachusetts, arguing against a result that would have left every property in Aquinnah unduly vulnerable to third-party claims of access. Sure enough, a win for Aquinnah.”
In another landmark case, Rappaport represented Edgartown before that same court, convincing justices to uphold three-acre zoning at Herring Creek Farm. The court’s decision, Lew said, protected the health of the Island’s coastal waterbodies against developers and their squad of high-powered Boston attorneys.
Fain Hackey, a partner at Rappaport’s firm, described Ron as a powerful legal mind who also understood the importance of community outreach and organizing. “He was the closest thing to a mayor this Island will ever have,” Hackney said.
Rappaport also maintained an active social presence, attested to by Mary Kenworth, co-owner of the State Road and Beach Road restaurants, who happily remembered what she called Rappaport’s “pregame” and “postgame” updates on upscale dinner parties and other events he had attended.
Rappaport, she said, was a wonderful friend and a staple in the Island community.
“This seems like a moment I should say ‘I hope you rest in peace,’” she said to Rappaport, “But I’m not sure I do. I think maybe I hope that you live it up in the afterlife and keep the party going.”
Julia Rappaport, Ron’s only child, was one of the speakers on Saturday. Before she took the podium, the lights at the Ag Hall briefly went out. She and other speakers took it as a sign of Ron’s presence, still strongly felt, making itself known.
“That’s the second time that’s happened when someone has been talking about Dad in a public setting,” she said. “So, we get it,” she added, to her father, drawing a knowing round of laughter from the crowd.
“We are here to honor a man who loved this Island so deeply that he dedicated his life to it,” she told the crowd.
Despite her father’s hard work and what she described as a “raging social life,” she said that he was a committed father and a role model.
During a rough patch at college after a breakup, she recalled, she was taken aback when her father offered to drop what he was doing and take a late ferry to visit her. “‘What if I came to Cambridge?’” she recalled him saying. Though she dismissed his plan, he told her that it was a done deal, and soon enough showed up at her door.
“He was holding a single random flower that he either bought or found along the way,” she said. “It was one of the nicest things anyone has ever done for me.”
The last to speak on Saturday was Steve Ewing, who shared his poem “An Oak Bluffs Boy, an Island Man” in honor of Rappaport. The poem describes Rappaport taking the helm of a ship on a foggy night and steering it to shore.
“For all his life for Vineyard’s sake / his legacy is the bow wake / Bless you Ron / our honest friend / forever will you steer again,” Ewing read.
