Reynolds, Rappaport, Kaplan & Hackney turns 30

So much for the sleepy country practice idea.

Co-founders Ron Rappaport, left, and James Reynolds in the offices of their 30-year-old law firm. Photo by Sam Moore

Thirty years ago, when Jane Kaplan, Jim Reynolds, and Ron Rappaport decided to hang out their shingle, they decided to hang it on a pretty impressive piece of property: a sprawling old colonial on Cooke Street in Edgartown, the same building that now houses their 20-plus-person firm. Except back then there were just the three of them: Jane, Jim, and Ron, along with Jim’s secretary, Tricia Willoughby, Ron’s secretary, Julie Higdon, and Debby Hale, their office manager. As Ron recalls, “Taking on this building at the beginning was clearly a leap of faith for us.” Jim was even more direct: “It was downright scary. We were taking on a big mortgage, we had to gut the place, it was a major effort, and it was on all our minds.” But on a brighter note, “It was actually great,” Ron said; “we each had our own floor, we had plenty of room, we never got in each other’s way.”

For Ron, coming to the Vineyard was a homecoming. He was born on the Island, son of a doctor, and went to the Oak Bluffs School and Martha’s VIneyard Regional High School before heading off for Stanford. After Stanford he went to Washington and worked for Ed Brooke in the Senate for a couple of years, then moved to Boston, went to BC Law School, and met his wife- and partner-to-be, Jane Kaplan, while studying for the bar. Jane had just graduated from Yale Law School. Over the next 10 years, they both would join Boston firms; Ron became a partner at Friedman and Atherton, and Jane a junior partner at Hale & Dore. But life has a way of telling you not to get too comfortable.

“After 10 years,” Ron said, “our daughter Julia was born, and we couldn’t figure out how to make life work with both parents being trial attorneys. I had been back to the Island around that time, cleaning up my father’s affairs after he died, and I realized I knew a lot of people here and I really liked it here. So we took a step back and said, Why not create our own firm on Martha’s Vineyard?”

Meanwhile Jim was already on the Island practicing. “I came to the Vineyard right after I graduated from law school at Villanova in 1976. I had never been to the Vineyard, but came here for a job interview, and I guess you could say the Island spoke to me.”

It turned out that Jim and Ron had a mutual friend on the Island, Dennis daRosa, and when Ron told him that he and Jane were thinking of coming back and starting a firm, Dennis put them in touch with Jim. As the corporate mythology goes, they all went out to the Home Port, talked over dinner, and discovered they shared the same ambitions, goals, and dreams. And before long, they were printing up business cards.

Looking back, it seems as though the three partners made a seamless transition to their new practice, but in reality, the plan didn’t exactly play out the way it was drawn up.

“What happened ended up being different than what we thought,” said Ron. “We thought we’d trade intellectually stimulating work in Boston — which left no time for family life — for a reasonably mundane and boring law practice with an emphasis on the family. Also, we thought if we did a good job, we could end up getting our local clients’ off-Island work as well. We were wrong on both counts. Turns out that our Vineyard clients have their other lawyers in Boston, New York, and L.A.”

But the pleasant surprise was that the work turned out to be anything but mundane. “The legal work we’ve done here has been, for the most part, really interesting,” Jim said. “We couldn’t have imagined that. What we thought was going to be a sleepy country practice didn’t turn out that way at all.”

This good fortune was partially a result of the skills and determination that Jim, Jane, and Ron brought to the table, but it was also a product of changing times. “When I first started here,” said Jim, “there were 10 or 12 old-school lawyers who’d been here forever and practiced in a certain way. Then, [starting] in the ’80s, property values started escalating, the Clintons came, and new people came with high expectations. We grew our practice to meet those expectations.”

Today, Fain Hackney is a partner and serves as managing director, Jane has retired from the firm, Jim and Ron have surrounded themselves with a strong supporting cast, and Reynolds, Rappaport, Kaplan & Hackney is the largest law firm on the Island.

“We do a lot of work with municipalities,” said Ron, “I serve as counsel for every town on the Island except for Tisbury, but the main driver for the firm is real estate, which is really Jim’s strength. But most all of the cases I argue in court flow out of real estate matters, so there’s a real continuity to our practice.”

Many of these cases have been very high-profile and have had far-reaching consequences. Just last month Ron represented the town of Aquinnah against a group of property owners who had sought to develop landlocked parcels they owned off Moshup Trail and gain rights of access. The Massachusetts Supreme Judicial Court ruled they have no such rights of access.

In a quote to the MV Times, Ron said, “Had the decision gone the other way, it would have opened up the entire town for development; it would have put a burden on most property owners, because their property would be subject to a cloud on their title in that an access road to a landlocked parcel could be located on their property; and it would have undermined a substantial public effort to buy land for conservation.”

In another high-profile case, in 1997, Reynolds, Rappaport represented the town of Edgartown in a landmark decision where the Supreme Judicial Court upheld three-acre zoning in the town, the largest minimum acreage requirement ever allowed in Massachusetts. “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,” said Ron, “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.”

And in another recent case with Island-wide ramifications, Reynolds, Rappaport won a judgment in the U.S. District Court for the District of Massachusetts that prohibits gaming on tribal lands, although the case is now on appeal.

In the course of handling so many high-profile cases for so many years, the firm itself is often in the public eye, particularly Ron, who handles much of the trial work and who, with his nimbus of gray hair, is highly recognizable. “Sometimes there will be a decision that’s unpopular with some people, and of course, it’s a small Island and you’re always going to run into these people,” said Ron. “But we try to call everything fairly, so overall it’s been fine. Actually, the most public feedback I ever got was when I was a governor of the Steamship Authority. People were always stopping me on the street to tell me how to make the boats run better.”

In an age of pop-up this and pop-up that, 30 years seems like a very long time — so what’s the special sauce that holds this partnership together? “Can I just say something about my partner?” said Ron. “It’s been 30 years … my wife was a partner, but stopped practicing about 10 years ago. I couldn’t have found two better law partners than Jane and Jim.”

Jim leaned back in his chair and said, “It’s pretty amazing, but I agree. We’re consistently on the same page; it’s a rare thing. Of course we have differences of opinions, but we always find common ground, and it’s been tremendously rewarding. We know each other well enough to know that if something is really important to one of us, you just step back and say, That’s fine.”

“We don’t operate by majority vote, we operate by consensus,” said Ron.

Both Jim and Ron are in their 60s, so it’s only fair to wonder what’s next, but when you talk to the two founding partners about it, retirement is not something that seems to be at the top of their minds. “I work hard,” said Ron, “as hard as I’ve ever worked, seven days a week. I enjoy the practice and have not cut back, and don’t have a plan in mind to do anything else.”

“I don’t have any plans for going anywhere either, but let’s face it,” said Jim, “we have limited time. I think we’ve planted a lot of seeds here among our colleagues, and I just know that when the time comes and we do leave, that these people will continue to build and enhance what we’ve started. And I know that when I walk out the door that last time and look back, I’ll be able to say, ‘Wow, what a ride it’s been.’”

Correction: An earlier version of this story incorrectly spelled the name of Dennis daRosa as Derosa.