Martha’s Vineyard is not noted for its penthouses, given the Island’s building height restrictions; urban skyscrapers are generally better suited. But atop Edgartown’s Harbor View Hotel & Resort is a penthouse of three thousand square feet, a well-situated sentinel with a 360-degree vista. There lives Bob Carroll, who brokered one of the sweetest real estate deals in Island history: to reside in the top-floor aerie for the rest of his life, overlooking the Edgartown Light and an expansive sweep of land and water beyond.

Ask anyone who knows him. Bob is a man of contradictions – poor, rich; kind, ruthless; creative, intransigent. Put the chemistry of these qualities into a test tube, combine them with a splash of Island idiosyncrasies, and you get a fiery and fearless entrepreneur, a citizen determined to make a difference despite the cost, a man who handcrafted much of what is downtown Edgartown today. Peter Bettencourt, who served as Edgartown’s town administrator for forty years, smiles as he describes Bob: “You may not agree with him, but he always tells it like it is – with passion.” Bob’s story starts with the tale of a boy who lived in an Edgartown very different from that of Edgartown today.

Growing up in the 1920s and ’30s

An energetic six-year-old boy runs the streets between his home on South Summer Street and the docks in Edgartown, which he later describes as “a smelly town that you wouldn’t recognize, a place marked by rotting fish smells and shanties on the shore.” The boy is no stranger to poverty. Relegated to the South Summer Street end of town, the poor section in those days, Bobby and his parents live in the Jernegan House, which later becomes part of the Charlotte Inn. His father, a lifetime alcoholic, was a butcher; his mother, a devout Catholic and a chambermaid. Both parents worked at the Charlotte Inn when it first opened after its purchase by Phil Pent, who married Charlotte Reynolds of New York City and named the inn after her.

To his good fortune, the boy is a “bluebird.” His neighbor Alfred Hall, who serves with Henry Beetle Hough on the school committee, reminds young Bobby that he is smart, that he is a bluebird and that the bluebirds are the highest reading group in first grade.

During sixth grade his favorite teacher, Frances Hayes, inspires him to be an avid reader and by the end of that year Bobby is reading Anthony Adverse, a gargantuan picaresque novel about a poor boy who was raised by a Jesuit priest and made his way to fame and glory. “I was eleven years old and read the whole story,” Bob says, “a real feat.” Anthony Adverse, written by Hervey Allen, became one of the most popular novels of the 1930s and in 1936 was made into a movie starring Fredric March and Olivia de Havilland. Who knows how much the nurturing of a neighbor, the skills of a teacher, and the impact of a moving book touched the life of young Bobby, for the boy becomes an Anthony Adverse himself, learning to surmount many odds and to make his way on a circuitous route to his penthouse on North Water Street.

Bobby worked as a fisherman when he completed high school, then he joined the Army. Ever contrary, he refused to join Officer’s Training School, an invitation that came as a result of the high scores he obtained on his Army entrance exam. Instead he fought at Iwo Jima and earned a bronze star. This young man cared not for status; he wanted to be in the thick of things, rolling up shirtsleeves, engaging with people. It wasn’t always a smooth road.

“My two biggest demons were drinking and smoking,” Bob confesses, “and each was the devil to shake.” Though he has been sober for fifty-eight years, Bob still talks of his debt to his neighbor Charlie Teller, who convinced him to join Alcoholics Anonymous. A painting of Teller’s house adorns Bob’s living room wall in the penthouse. Smoking was another early vice. “When I worked as a car salesman [at Renear Ford in Vineyard Haven],” he says, “I had a cigarette in one hand and a cup of coffee in the other.” When a spot showed up on his lungs at the age of thirty-five and the doctor broke his ribs to remove a growth, he stopped smoking. Bob’s has been a life punctuated by high drama. His blue eyes sparkling with fun, he admits, “I don’t work in moderation, I don’t play in moderation, and I don’t even chase women in moderation.” Despite that, Bob stayed married to his first wife, Lucille, for twenty-five years, and they had four daughters together.

An aptitude for business

“Once I stopped drinking,” Bob says, “I learned I could do anything.” He viewed his environs with a new eye. “We needed a restaurant,” he says. “But I didn’t have a dime. I never saved money.” He appealed to John Nevin, who had inherited the property that is now Nevin Square and who owned a car dealership on the waterfront. John saw the potential in Bob’s restaurant idea and vouched for his trustworthiness by offering him a lease with an option to buy. With a handshake came the birth of the first Seafood Shanty in 1961.

Soon lines of hungry diners snaked down the street. He instructed his waiters and cooks never to appear in a dirty apron and his waitresses to bring all complaints to the kitchen, then he went out to socialize with the complainer. “I wanted people to be happy,” he says, “to have fun. Sometimes I even had a piano player and a singer.” When the growing popularity of the Seafood Shanty made it hard to manage, Bob tried a new tactic: Raise the prices. “It worked,” he says. “We served less people and made a lot more money!” The business model became so well known that Bob was invited to do a seminar for business students at Boston College.

“The success of the Seafood Shanty was my first big break,” Bob says. “Still, I had to keep a close eye on the finances. I had to save enough money to pay the bills for January, February, and March. By April, I could begin to borrow again to meet the needs of the busy summer season.” He borrowed only what he knew he could pay back, never defaulted on a payment, never paid a late fee. “That was my code,” Bob says. “I always kept my word.”

By 1966 Bob had proven himself a reliable borrower and a successful entrepreneur. His mentor and neighbor Alfred Hall knew a group of summer people who had purchased the Harbor View Hotel from the estate of its original owner, Dr. Thomas Jackson Walker. The second owners were trying to sell the place. “I’m saving this for you,” Hall poked him. “Get moving. You can own this place.” At first Bob laughed, then he realized that his friend was serious. He appealed to Frank Nickerson at the Falmouth Bank. Like Alfred Hall, Frank believed in Bob. “I need $250,000,” he says he told them, though the asking price of the hotel was $225,000. He knew that he’d need the additional money to hire a staff and to get the place up and operating. Once again, despite the fact he had accumulated no real savings, the bank financed the hotel and adjoining property and thus banked on Bob as well. In 1968 he became the third owner of the Harbor View Hotel, with partner State Senator Allan Jones.

With typical zeal he set out to remodel, one floor at a time, and again borrowed only what he needed and knew he could pay back. “Can you imagine that in the original hotel the bathrooms were built on the front side of the building?” Bob says with a laugh. “Imagine sitting on the can with that incredible view!” So one of Bob’s first initiatives was to move all the toilets away from the front side of the building and open the awesome views of the harbor, Chappaquiddick, and the Edgartown Lighthouse to the living areas of each room or suite.

Bob talks about the history of the hotel, built in the late 1800s. Cottage Two was moved from Katama during the time when a railroad ran there. “Not sure
exactly how they moved it,” Bob says, “but I hear it may have been across the ice in the wintertime. That cottage had fifteen-foot ceilings!”

Eventually Bob joined all the buildings of the Harbor View, combined porches, enlarged the Edgartown Room, and did whatever he could afford, whatever made sense, and whatever pleased the public. “In the 1970s the public wanted motels,” he says. “So I built a rear section of motel units. Within two years that project was so popular that it paid for itself.” Other people, usually the older set, preferred the traditional rooms with dark woodwork and gray paint. Bob remembers this story with a smile: “J.P. Morgan’s private secretary and a friend came every year to the same old room in the original Harbor View. One year I did a complete remodeling, repainted the walls in brighter colors, refinished all the woodwork, and could hardly wait for the arrival of the two seasonal visitors. Can you believe it? They didn’t like it! We laughed about it later.”

Once he knew the Harbor View investment could be solvent, Bob looked around for new projects. The nearby Kelley House, then owned by Dick Colter, caught his eye from his office in the Seafood Shanty. He obtained financial backing and bought the place for $495,000. When the Kennedy hearings were to take place in 1970, every room was reserved. But the hearings were postponed and Bob lost all the bookings. “I learned my lesson,” he says, “From now on I’ll ask for a three-day deposit.”

In 1974 he got wind of Steven Spielberg’s Jaws project. He got a call asking for fifty rooms at the Kelley House. “Done,” he replied, “but I need a deposit of $25,000.” He got it. By the time Jaws was finished, Bob and his various Edgartown businesses had netted more than one million dollars. Bob played the role of a councilman in the movie: You’ll see him in the scene where the fisherman Quint scratches the blackboard during a meeting. To this day he still receives royalties for that performance.

Invested in the community

Among Bob’s adventures were the acquisition of a pilot’s license and the purchase of a small plane. “They called me to get Ted Kennedy quietly off the Island in 1969,” he says. What he doesn’t say is that he used his plane repeatedly to help his friends and neighbors as well. Ted Morgan, who served as an Edgartown selectman for more than thirty years, relates this about Bob’s good-heartedness: “My son Dale was deaf and often had to travel to Boston or to Northampton for medical appointments. Bob used his plane to help our family and many other families as well.”

Bob’s entrepreneurial excellence drew him into many other business affairs in Edgartown, among them ownership of an ice cream bar and Edgartown Marine. He boasts that his purchase of one property in Katama put his four children through boarding schools and college. “I took care of their teeth and their educations,” he says. “I bought the place for $210,000, then I turned around and sold the house alone for $200,000 and a lot for $50,000. I divided the rest of the land into seventeen lots and sold off each of them. You do the math,” he chuckles.

The success of Bob Carroll’s real estate and business ventures was complemented by his desire to make a civic contribution to Edgartown. “If you don’t give back, you haven’t done anything,” he says. “It’s my town, and it’s one of the most beautiful places in the world.” Bob was a selectman for about a decade in the 1960s. “What’s my legacy?” he asks. “The Edgartown sewer project. When I owned the Seafood Shanty in its early years, we had to pump out sewage every single day. Sounds mundane but that sewer project made a huge difference to the town.”

Bob boasts too of his role in protecting Katama Farm. During his years of public service, he once chaired the Katama Farm Committee, and he helped to negotiate getting an option from The Nature Conservancy to purchase the farm. He and his colleagues raised the funds from public subscription. “We were really motivated,” Bob says, “because we heard that the land was to be sold to developers. After we completed the purchase to protect the land, we kept a hundred acres and turned it over to the Edgartown Conservation Commission. Today when I look at Katama Farm, I’m proud of that work. Everyone can enjoy it now.”

When Bob sold his share of the Harbor View in 1986, he used his considerable real estate savvy to negotiate a particularly plum caveat: He would obtain the penthouse on the top floor and live in it rent-free for fifty years. His second wife, Rebecca, oversaw the renovation of his new home by designer Twanette Tharpe of Edgartown. “Twanette was a genius,” he says. “Just look at this place. My father never made thirty dollars a week in his lifetime. How I wish that I could invite my mother and father to come up and sit with me for a half-hour here today.”

From the windows of the mammoth living room, you see downtown Edgartown and all the way westward to Katama. To the south you can admire the Edgartown Lighthouse. A bit to the east is Chappy. And on the north side, Bob watches the Oak Bluffs fireworks every August. The walls are adorned with original paintings and photographs: the Jernegan House where Bob grew up; the Teller House; the original Seafood Shanty; a prize-winning Peter Simon photo of Bob’s liver-spotted hands, folded near the top of his walking stick. “Forget my funeral,” he says. “I want to have a party while I’m alive. I want to see who comes!”