The Harbor View Hotel closes down during the last two weeks of the year. During this time everything appears quiet at the tip of Edgartown. But appearances can be deceiving.

Notice the lights blazing in the penthouse apartment. This is the home of Bob Carroll and has been ever since he sold the hotel in 1986. It was part of the contract that Mr. Carroll could build this penthouse and live in it until he died. And for two weeks each winter, during the holidays, he is the only soul alive in the hotel.

But this is not some modern day Rapunzel story with an 87-year-old man playing the lead and waiting for someone to rescue him from his castle turret. This is Bob Carroll we’re talking about, after all. If someone ever tried to lock him away he’d just end up owning the castle outright, putting in sewerage to tame the fetid moat, and building a nice development on the vast acreage.

Bob Carroll
Ivy Ashe

He’d also get the girl and woe to the one who tried to do him wrong.

Mr. Carroll has a very long memory for that sort of thing.

Case in point, when he was a boy he worked for a time at the Edgartown Yacht Club. “I washed dishes there when I was about 13,” he said during an interview at his penthouse apartment. “The [expletive deleted] they fed us, I never forgot it.”

To this day, Mr. Carroll refuses to join the yacht club.

Bob Carroll was born, in his words, “a poor ragamuffin” in 1924 on South Summer street in Edgartown, across the street from what is now the office of the Vineyard Gazette, which at the time was the local poorhouse. His mother rented a room for four dollars a week.

“It sounds funny but four bucks were damn hard to come by,” he said. “This was in the early 30s when guys were digging an opening through South Beach with shovels, and the town was paying for it but you could only get two days a week of work at 25 cents an hour.”

So how did he go from ragamuffin to one of the wealthiest men on the Island, owning at one time the Seafood Shanty, Harbor View Hotel, Kelley House and vast areas of prime Edgartown real estate?

The short answer. “I never made a profit. If you make a profit, you’re stupid.”

The long answer. He earned it the old-fashioned way, by working very hard and, at the age of 28, getting sober.

“I was a very bad alcoholic. I came from a long line of drunks. When my oldest daughter was born I kept falling out of bed and waking her up. Then an old friend of mine, Tommy Teller, his father came and got me. His brother and I had been on a toot Fourth of July weekend and his father said, ‘You’re coming with me.’ He was that kind of a guy, and he took me to my first AA meeting.”

Once Mr. Carroll got sober he got busy.

“When I got sober I started to get respect. I found if I could stay sober I could do almost anything I wanted to do. I didn’t always want to do good things. I haven’t been an angel. But I’ve had a good life.”

In the 1950s Edward W. (Peter) Vincent owned a small coffee shop in town that he leased to Mr. Carroll, whose newfound sobriety made him not only a worthy credit risk but a shrewd businessman.

“We had guys who would pay 10 cents for a cup of coffee and sit there all morning so no one else could get in, so I raised the price of coffee,” Mr. Carroll recalled. “Then I realized they needed another restaurant in Edgartown. Bob Nevin’s brother John owned the first building I bought. I made a little restaurant out of it.” That restaurant was the Seafood Shanty, which would become a landmark eatery in Edgartown.

Mr. Carroll continued to be successful with a basic business model.

“Anything I owned, we had a good time. I didn’t believe in being miserable. We had lunch and dinner and a bar and that was hard. I was newly sober. Every once in while I had to go for a walk. Say a few AA prayers.”

In 1965 he expanded by buying the Harbor View hotel for $225,000.

“The Harbor View when we bought it, the living room was full of old thunder jugs and piss pots, thunder jugs were the ones you sat on. They didn’t have any bathrooms when they built this hotel. What they had done, when they put the bathrooms in, they put them right in front of the hotel, right up the front. Sit on the throne and you had the best view in the world,” he said.

Mr. Carroll then bought the Kelley House and Edgartown Marine. “For the real estate,” he said.

Although the Vineyard can often seem separate from the life of the rest of the world, history does have a way of including the Island, mostly because of all the power brokers who visit. Mr. Carroll earned his place among this set too.

When Ted Kennedy had his problems on Chappaquidick in July 1969, it was Mr. Carroll who received one of the first calls for help. “I had my airplane and flew them all out of here. Jim Arena [the Edgartown police chief] called me,” he said.

His help did not go unnoticed. Later, in 1972, after he became senator, Ted Kennedy proposed the Nantucket Sound Islands Trust Bill, “with Bill Styron and a bunch of goddammed snobs.” In other words, Mr. Carroll was not a fan of the bill and determined to stop it, feeling it put control of the Island in the hands of the federal government.

“I was president of the Chamber of Commerce. Dudley [K. Dunn] Gifford who was Teddy’s right hand man, said, ‘What do you think you’re going to do against the senator?’

“So we all went down for a hearing in Washington and we were walking down the hallways and Teddy comes walking out of his office at the senate and he said, ‘Bob, what the hell are you doing here?’ So that was fine.”

Fine meaning, well, there are many sides to the issue, but in the end the bill did not pass.

Of course, no one rises to the top and maneuvers among backroom power games without making enemies. A walk down the streets of Edgartown might uncover more than a few who do not view Mr. Carroll in the most angelic of lights. But perhaps his longest standing feud was with the late editor of this newspaper, Henry Beetle Hough. As Mr. Hough is no longer present, the floor belongs to Mr. Carroll.

“Henry’s problem was he always saw me as a ragamuffin and he couldn’t see me owning the Harbor View Hotel,” he said.

The two had arrived in Edgartown at about the same time. Bob Carroll, born poor on the Island, just when Mr. Hough washed ashore having been given the Vineyard Gazette as a wedding gift. The two Edgartown town fathers continued to spar during their lifetimes. The Ivy League country editor and ardent conservationist versus the Island kid with the newly-earned largesse set on developing the Island as he saw fit. One battle came to a head soon after Mr. Carroll bought the Harbor View.

“We owned all this land across the street right to the lighthouse,” Mr. Carroll remembered. “And I decided I wanted to build two houses across the street and I applied for permission to fill it and Henry took up the cudgel . . . came after me hammer and tong. So one night I got every heavy truck on the god damn Island, we loaded them with fill and at 6:30 a.m. started filling the land in. We finally got a court order to stop around noontime.”

It would be wrong, though, to characterize the two men as just conservationist and developer, the public good standing up to commerce. After all, in the end Mr. Carroll gave the beach on the inside of the harbor to the town. He was also an early member of the Martha’s Vineyard Preservation Trust and this was not merely a case of the fox getting into the henhouse. Mr. Carroll was instrumental in keeping Katama Farm forever wild.

But the two men did continue to butt heads to the point that Mr. Carroll was one of a group of businessmen who founded a rival newspaper, the Martha’s Vineyard Times.

“I put well over a half million dollars into it, and Eddie Redstone put 750,000 plus in it.”

Mr. Carroll didn’t last long as a newspaper man, though, and eventually turned the paper over to the employees.

During his lifetime Bob Carroll has not just watched but participated in the making of modern-day Edgartown. As a restaurateur, hotelier, real estate developer, Edgartown selectman, county commissioner, founder and board member of Martha’s Vineyard Community Services, the full list of his bona fides are too many to list; he is a man who, as the saying goes, knows where all the skeletons are buried. In fact, he still visits them.

“I promised I’d piss on their graves,” he said.

These are his friends, mind you.

“My partner, Pete Vincent, and a couple of others. Small towns, this is a great town. I think it’s the best town in the world.”