Ronald Hall Rappaport


Ronald Hall Rappaport of Chilmark, Martha’s Vineyard’s foremost attorney, whose love for the Island was exceeded only by his devotion to his family, died unexpectedly on June 7, just nine days shy of his 75th birthday. 

Born June 16, 1949, in Oak Bluffs, the second child of Dr. David and Adeline Rappaport, he left a position at a major Boston law firm in 1984 to open a law practice in Edgartown with his wife, Jane Kaplan, following the birth of their daughter Julia.

It was a hallmark of his life that his professional success was inextricably tied to his personal relationships. He adored traveling, watching his beloved Celtics (and Patriots and Red Sox), and thinking over nitty-gritty legal issues with his wife. He cherished his daughter, always answering the phone whenever she called, even if he was in the middle of a meeting, even if she was just calling to say hi. He doted on his two beloved grandsons, gossiped and laughed with his siblings, and cheered on the successes of his nieces, nephews, grandnieces, and grandnephews. 

Over four decades, he built an unmatched reputation as a skilled lawyer, trusted advisor, and champion of Martha’s Vineyard, widely sought after for his thoughtful counsel and deep appreciation for community values. As municipal attorney for five of the six Island towns and the Martha’s Vineyard Land Bank, he fiercely guarded the Vineyard against overdevelopment, successfully representing the Island in several landmark legal decisions. He served on numerous civic boards and committees, including more than seven years as a Steamship Authority governor during a particularly fractious period in the 1990s. At the time of his death, he chaired the board of the Martha’s Vineyard Bank, as well as its charitable foundation, which he helped to found.

His untamed halo of hair made him instantly recognizable, whether circumnavigating the Island on his bicycle, offering legal advice at town meetings, watching the Celtics from the owners’ box, or sharing laughs at the many social events he attended — not infrequently two or three in a single evening. He was at home in every setting, and his friendships spanned every walk of life.

The son of David, a prominent Island physician, and Adeline, who was a teacher and later founded Dukes Travel Service, he talked fondly and often of his carefree childhood in Oak Bluffs, where he attended the Oak Bluffs School and roamed freely in the neighborhood, riding bikes and playing baseball with a close circle of friends.

He attended the Middlesex School in Concord and then Stanford University, graduating in 1971. That summer he moved to Washington, D.C., to work for U.S. Sen. Edward Brooke, a seasonal resident of Oak Bluffs who was the first African American elected to the Senate by popular vote.

He ran the Boston office for Sen. Brooke’s re-election campaign while attending Boston College Law School. It was at a bar-review course after completing law school in 1975 that he met his future wife, Jane. In each other they recognized shared values, shared dreams, and a natural, easy companionship. They married in 1977.

Both gifted lawyers, their decision to move to Martha’s Vineyard soon after Julia’s birth was an affirmation of their commitment to community and to family, as they sought, in theory, to achieve a more realistic work-life balance. Teaming up with partner Jim Reynolds, however, their law firm — now Reynolds, Rappaport, Kaplan and Hackney — quickly grew to become the Island’s largest. 

He was an expert on zoning, and steeped in the history of it going back to the 1970s, when the first comprehensive zoning established a baseline for the Island to protect itself from unwanted development.

Among his most significant legal victories was a 1996 Supreme Court case that upheld three-acre zoning in a trial against developers who wanted to turn Herring Creek Farm in Edgartown into luxury housing. He also represented the town of Aquinnah in efforts to prevent the creation of a bingo hall.

He was instrumental in bringing the Martha’s Vineyard Hospital to stable financial grounds in the 1990s. He helped to organize the charitable organizations MVYouth and Vineyard Youth Tennis (now Vineyard Family Tennis), and was a key figure in the creation of Test MV during the COVID epidemic. In 2000, he received the Spirit of the Vineyard Award for his many contributions to the Island.

In addition to his wife and daughter, Ron is survived by his son-in-law, Jack Spencer of Newton and Chilmark; and grandsons Sam Haven Rappaport Spencer and Charlie West Rappaport Spencer. Ron passed on his love of biking and his curly hair to Sam, and his impish, devilish charm to Charlie. He is also survived by his loving siblings, Alan Rappaport of Chilmark and Florida and Susan Cohen of Newton, and their spouses, Jill Rappaport and Fredric Cohen. He is survived by nieces and nephews who thought the world of him: Alex Rappaport and his wife Catalina of New York, Hilary Rappaport and her wife Lindsay of New York, Michael Cohen and his wife Mara Green of Newton, and Cindi Samuels and her husband Greg of Chagrin Falls, Ohio. He is also survived by grandnieces and grandnephews: Harper and Reese Cohen, Emilee and Roxie Samuels, Lyle Rappaport (born one month before grandson Charlie), and a new grandniece that will join us in several months, whom Ron could not wait to meet.

Donations can be made in Ron’s honor to the Ron Rappaport Fund at MVYouth, Martha’s Vineyard Bank Charitable Foundation, and Martha’s Vineyard Community Services. A public celebration of his life is being planned for a future date.