They met on the equivalent of a blind date some 23 years ago, set up by a mutual friend. The subsequent marriage of Jim Reynolds and Ron Rappaport’s legal practices has worked because of complementary roles. One wears his suits off the rack; the other prefers custom tailoring. One works in a third floor office, out of view; the other can be found downstairs, unfailingly in the middle of the fray. One mostly hunts; the other mostly gathers. And the hair — well, what’s left to say?

Interviews by Mike Seccombe

Jim: We were brought together by Dennis and Candy daRosa, who had become friends to my wife Barbara and me when we moved to the Island in 1976.

As I’ve heard it, back in 1983 or ’84, Ron went to Dennis and said [his wife] Jane and he were looking to come to the Island and asked who would be the best person to affiliate with. And Dennis said I would. So Dennis facilitated a dinner at the Home Port and that’s where it all began.

Ron had been in a successful practice in Boston, as had Jane.

So we met — and really it was not just Ron and I, but the three of us who were getting together, because Jane had been an extremely accomplished attorney as well. And I liked them a great deal as people and I was very impressed with their talents as lawyers, to the extent I could glean that from a social meeting.

My practice at the time was in a bit of transition. I had been in with some other lawyers, who were heading in different directions and I think Ron decided to test the waters. He came to the Vineyard a day or two a week and opened an office for his then-Boston firm.

So he had a rented office in the building where I was working with the other lawyers, just up the street. He was in the next office a day or two a week, and it was a nice way to get to know each other better. We got to collaborate on a few matters and get to know each other over time and I became extremely impressed with him as a lawyer and as a person.

Then at some point we began discussions about formalizing a relationship, as he began to see that it would be possible for him to come to the Vineyard and still have interesting and stimulating work. I think that was one of the concerns initially for both him and Jane — that they came from such stimulating practices. Would they be able to find similar work here?

I think observing me and seeing the kinds of work I was doing and kinds of clients I was representing, he was persuaded it could work.

The division of work was very natural. His skills were different from mine; he was trained and practiced as a litigator, a trial attorney, and I was a transactional real estate lawyer.

Early on we identified those as the two primary focuses of our practice.

Very critical was that fact that I was asked to serve as town counsel for Edgartown in about 1985, before we were actually a formal partnership.

The skills of town counsel were really beyond what I personally had. So we said as much to the selectmen, and they said, ‘You can be the town counsel, and to the extent you need litigation support you can work with Ron, but we can only name one person, not a firm.’

It became clear it was something Ron was better at than I. So much of it is strategic litigation-type thinking. That’s not my forte. I think I served one year and he took over from me.

I think most people would say of me that I’m a pretty thorough practitioner. I’m careful, focus on details. Not to the exclusion of looking at the big picture, but I tend to spend a lot of time making sure every i is dotted and every t is crossed.

Ron is a big picture guy. He is fastidious about details; when he is trying a case there is not a detail he overlooks. But he has a lower threshold of boredom than I do.

I do love to be up here [undistracted in his third-floor office]. Away from the hubbub. Ron’s always there [in his ground floor office]. He’ll come out from time to time; he’s always keeping an eye on what’s going on, whereas I couldn’t care less. I figure other people will do that.

He’s irreverent and he’s fun and he’s instantly attractive as a personality. There’s a certain buzz that Ron generates in social settings. Me, I’m nowhere near as gregarious, much more low key.

I don’t think we’ve ever had a disagreement of any great substance over 22 years. We agreed from the very start we would act by consensus only. In the early days I had some concern I would be joining a husband and wife team and maybe I would get outvoted at some point. But it was generally Ron and I ganging up on Jane.

That doesn’t mean we don’t disagree, but to the extent someone has strong feeling about an issue, I can’t think of an instance where those feelings were not acknowledged by the others.

It’s remarkable when you think about it. It’s really driven ultimately by the trust and respect we have in one another.

If I were in a foxhole and the world was about to end, Ron is one guy I would like to have in there with me. He’s a tough guy and just the kind you would want in a difficult situation.

Ron: My oldest friend, growing up here in Oak Bluffs, is Dennis DaRosa. Dennis and his wife Candy were very close with Jim and Barbara Reynolds.

So — this would have been somewhere in the early 80s — Dennis basically fixed us up. He thought it would be a good idea for me to come back to the Vineyard and practice law here. He really liked Jim and felt he was an excellent attorney. He fixed up a meeting where we all had dinner, exactly like a blind date. Things took their course from that.

When my father died in 1982, I started spending time with his affairs — I was a partner in a law firm in Boston — and decided to test the waters here.

Then my wife Jane [Kaplan] became pregnant. In 1984, when Julia was born, Jane took leave for six months then extended it for another six months and then decided she could not figure out how to be a litigator with a major Boston law firm and be a mother.

So after much lengthy, painful deliberation we decided we would come to the Vineyard and open up a firm with Jim. We bought this building in 1985 or ’86, and the three of us opened up our law firm Reynolds, Rappaport and Kaplan. And here we’ve been for about 23 years. Jane retired, probably five years ago now.

I’d say Jim is Mr. Inside and I’m Mr. Outside. Jim is an outstanding real estate attorney — I think the best on the Vineyard. He would be at the top of the profession anywhere. He is extremely thorough and conscientious and meticulous and knowledgeable.

But he does not like and has nothing to do with litigation or court appearances, does not like speaking in public forums, at least in the legal context.

Back at the beginning of the practice, he was asked to be town counsel for Edgartown. His interest lasted up until the first annual town meeting. As counsel you have to field questions that often times come out of left field. Jim really does not like doing that. He likes to be thoroughly prepared for all that he does. Spontaneity is not, I think a strength he would say he has.

So I took over. I enjoy court work, enjoy the public battles involved in court cases, particularly in defending the towns and I enjoy town meetings. I represent five of the towns and the land bank and it often puts me in the public limelight. I also was on the Steamship Authority board for eight years, which was highly public and visible.

That’s the sort of role I’m comfortable in and I think Jim would be the first to admit that he is not.

So our practices have totally complemented each other.

I have the utmost respect in Jim as a professional and a person. I would trust him in anything. He is a perfect partner.

We are professionally close and are close friends as well, but our contact is almost exclusively in the office. The other time is family time. I have him during the day and Barbara has him at night.

He is a professional confidant and advisor and we each would drop whatever we’re doing to help the other one out.

While Jim’s practice focuses almost exclusively in real estate, I do quite a bit of it myself. If there’s ever a complicated matter I’m dealing with, I will bring Jim in. And whenever something is moving toward litigation — and unfortunately that happens with some frequency in real estate transactions — we will collaborate.

There are certain court matters he will do, but they primarily involve titles in the land court or proceedings relating to real estate probate court, but for the most part, not at all. While I tend to mix it up a lot more.

If I could choose a perfect partner to be in business with it would be Jim — and I should add my wife Jane.

Our practices and styles and strengths complement each other. There has not been one issue we have ever disagreed on, even politics; I can’t recall an election where we ever voted differently.

I’m sure Dennis daRosa is very pleased with his match-making abilities.