According to Jim Reynolds there were no law school courses devoted to where to practice law, whether to strike out for the big city or look for a small community. Law school was about the big ticket items, constitutional law, contract law, classes devoted to preparing would-be lawyers for the field itself.

Where to practice law was more about the heart.

For Mr. Reynolds his heart lay in a small town, even though he grew up in a city (Worcester), went to college in a city (Johns Hopkins), and attended law school in a city (Villanova).

“There was something about a small town that really attracted me,” Mr. Reynolds said in an interview in the conference room of the law firm he helped found: Reynolds, Rappaport, Kaplan and Hackney. The conference room is mostly quiet these days due to Covid precautions, and instead of holding court for legal meetings it serves as a way station for Red Stocking gifts.

On Dec. 31, Mr. Reynolds, 70, will retire after a legal career stretching back 45 years, all of it taking place on Martha’s Vineyard, a place he had never even visited until he came for an interview after graduating from law school.

“I was sort of captivated by the idea of life on an Island,” he said. But his career has been charted more by intuition than calculated appraisal. He even applied to law school on a whim, after Johns Hopkins.

“Hopkins was a school where everybody was going somewhere after college,” he recalled. “People went to med school, business school, law school, academia. And the only two that I really qualified for were law school or academia. And I don’t know why I chose law school, but I did.”

He didn’t really like it.

“I don’t think there’s too many people who would say they enjoyed law school,” he said. “It was a grind. It was a hard experience just to get through it.”

Upon graduating he sent out cover letters and resumes and got a call from Montgomery and Meisner, a firm located in Edgartown. He moved to the Vineyard in 1976, when the Island was being introduced to the world as the place Jaws was filmed. It was still a sleepy place back then, more outpost of locals and hippies than playground of the rich and famous. He arrived with his girlfriend who would soon become his wife, Barbara.

“From the very start, it was an idyllic life,” he said. “It felt just right. Our first office was on School street and we rented a house on Pierce Lane. So each day, I’d walk to work, from Pierce Lane, over across Main street, to School street, and walk back every night and I was just pinching myself the whole way thinking, look at this beautiful setting. I used to stop at what was then Dukes County Savings Bank at the head of School street and talk with the custodian there, and Jimmy Klingensmith would be on the steps of the courthouse and I visited with him each night when I walked home.”

Little did he know that walking the streets of Edgartown, chatting with his neighbors, was also forming the basis for his legal specialty, real estate law, which Mr. Reynolds contends is at its core about relationships and community.

His first year at the Montgomery and Meisner was devoted mostly to the Registry of Deeds. It suited him perfectly.

“I spent the first nine months of my practice there. It was invaluable experience, learning what is the basis for all that we do as real estate lawyers,” he said.

He likens it to detective work, the cold case files of property and place, often stretching back generations.

“It’s about the ownership of land and the history of the ownership and the relationship of rights of the various properties, one to another,” he said. “Do I have a right to look across your property out to the harbor so that I can continue to look at the water? Do I have an easement to do that? Is there some kind of an agreement between you as the owner of your property and me that you can’t do something on your property. It’s all these interrelationships which are very interesting. Originally, I thought I had to do a little bit of everything and I probably did when I started, some criminal defense, some divorce work. But ultimately I felt what I was most interested in and what I was probably suited for best was real estate law.”

After 10 years with Montgomery and Meisner, Mr. Reynolds decided to form his own law firm, and after being introduced to Ron Rappaport and his wife Jane Kaplan at a meeting at the Home Port Restaurant, the three attorneys set up shop on Cooke street.

On the surface Mr. Reynolds and Mr. Rappaport appear to be an unlikely duo. Mr. Rappaport is as outgoing as his hair which looks like it not only has a mind of its own, but is of many minds. Mr. Reynolds’s hair never extends beyond the property line. But the partners clicked and complemented each other.

Reynolds, Rappaport, Kaplan and Hackney was founded on Jan. 1, 1986. Asked why his name comes first at the firm, Mr. Reynolds said he does not really recall the decision making process but imagined it had something to do with him already being in practice on the Island.

Mr. Rappaport, on the other hand, remembers the reason vividly.

“We decided that whose name went first got last choice on office space,” Mr. Rappaport quipped.

Mr. Reynolds went to the third floor, which over the last three and half decades has become ground zero for real estate law on Martha’s Vineyard.

“Jim is the best real estate lawyer on the Island,” Mr. Rappaport said.

When asked how he feels about his longtime partner retiring, the usually loquacious Mr. Rappaport was momentarily at a loss for words. But not for long.

“Jim has been the best partner that anyone could ask for and I hold him in the highest regard,” Mr. Rappaport said. “I can’t come up with enough superlatives about him, and I will miss him.”

Others at the firm will also miss him, but none more than his longtime assistant and paralegal, Tricia Willoughby, who began working for him in 1985 when she graduated from college.

“He’s the only boss I have ever had, other than my father in high school and college,” she said. “We have been two minds churning away at the wheel. He has always been a teacher and mentor and I have learned from that and how to pass it along, too.”

“It’s emotional for sure,” she said of Mr. Reynold’s retirement.

Mr. Reynolds returns the praise of his partner and his assistant, calling them a second family.

“We complete each other’s thoughts and sentences,” he said about Ms. Willoughby, “which has been immensely helpful for me because I get a second pair of eyes on everything I’m doing.”

Through his long career on the Vineyard, Mr. Reynolds has had a unique perch to witness the changes to the Island, in particular as real estate values have soared to heights unimaginable when he started out. But again he sees this through the lens of relationships, the clients he has represented and other lawyers he has litigated with or against, often from big city firms as his small town became a world-wide destination.

He found it exhilarating.

“As the value of properties grew we as practitioners on the Vineyard had to up our games to respond,” he said. “And I found that tremendously stimulating. In terms of the lawyers that we were working with, the clients who are buying their, what I refer to as their summer cottages, and yet they have lawyers in New York, or Washington, or Los Angeles, or in London, or wherever they might be. And they had high expectations for us as the local practitioners, at least I certainly felt it myself. And if I’m going to hold up my end, I have to be good at what I do. It pushed me. I just wanted to be the best that I could be.”

Mr. Reynolds said he has tried to retire twice before, but this time he means it.

“I sent out a letter to about 75 or 100 clients in the past couple of days,” he said.

His first task will to be lay low, he said, at least professionally, taking the advice Ed Jerome gave his wife Barbara when she retired as a longtime Edgartown School teacher about 10 years ago.

“He said to Barbara, take the first year off and don’t do anything or volunteer for anything. Go through that process and then decide. So I think I’m going to sort of gradually test the waters and see what I really want to do.”

This will involve traveling with Barbara to visit their children and grandchildren who all live off-Island now, and exercise, a pastime that when talking about, the longtime real estate lawyer tosses his reserve aside.

“I’m an exercise fanatic,” he said. “Road cycling, yoga, Pilates, strength training ­— I do all of that.”

He is also looking forward to digging deeper into reading and gardening and volunteering, but not to sit on boards, which he has done throughout his career.

“I probably sat on almost every nonprofit board on the Vineyard at one time or another over the years,” he said. “And I think at some point I became more interested in being hands-on. I was a Big Brother to a young man who is now in his junior year in college. I worked at the Food Pantry. I realized I get more out of doing that type of hands-on work.”

And as for the law?

“I don’t I don’t think there’s much legal work in my future,” he said. “I’ve done that. It’s time to do something else.”