James Flight Alley died May 15 in West Tisbury, the town he loved and where he was a model of a successful small-town businessman and politician. His burial will be Friday at 11 am at the West Tisbury cemetery on State Road. A gathering will be held in September (on a day and time to be announced) to remember Jim and tell stories about his colorful life.
Jim was born March 8, 1932, the son of Albion Alley and Maryann Flight Alley. His grandfather, Antone, was a Portuguese immigrant who found success on the Vineyard as a fishmonger and later as a farmer. The family story is that Antone became called Alley as a nickname based on his pronunciation of the word “halibut,” which was one of the fish he cried for sale as he pushed a cart around Oak Buffs. Jim remembered his grandfather chiefly as a farmer.
Jim Alley loved West Tisbury and lived there almost his whole life. Although he and a friend, Tony King, went to California after graduating from Tisbury High School in 1950, he soon came home, settled down, and married.
Jim was a successful small-town businessman all his life. He had a head for figures, an excellent memory, and a flair for the theatrical which served him well as a salesman. Although he worked for a time as a bartender at the Boston House, which gave him material for many of his famous stories, many important years of his life were spent at the family business, Alley’s Store, formerly the S.M. Mayhew Store, which his father had bought. Eventually, Jim and his younger brother, John, and his older sister, Phyllis, took over running the store, and Jim “inherited” the job of postmaster from his father. He also expanded the business, adding a laundromat and a carwash. Simultaneously Jim was in the real estate business with his father, at a period when they, and later Beverly King, were the only agents in West Tisbury. Jim loved horses all his life, and Jim and Bill Honey bought Misty Meadows Farm in 1972 and ran a full-service riding farm, offering riding lessons, trail rides, a summer camp, and buying, breeding, and selling horses. Misty Meadows came to specialize in the Missouri Foxtrot Horse. The farm would produce foals in West Tisbury, drive them to Missouri, where they commanded a higher price, and return with adult horses for the riding school and trail-riding business.
After retiring from the post office, he and his wife, Ann Bassett, operated Alley’s Real Estate, and his friend Lenny Jason joined the business. In later years he became a used car dealer. Many remember him in his Woodland shed office, with helpers Gordon “Bob” Bassett and John Rogers, and his employee, daughter Lisa. An old-fashioned businessman, Jim guaranteed his cars and often provided financing. A small town businessman trusts his instincts. He was one of the few on the Island who would offer financing to Brazilians.
Jim was also the consummate small-town politician. All his adult life, Jim followed the often-ignored principle of democracy, “If you don’t like the way things are going, do something about it.” As if he weren’t busy enough with Alley’s Store and a real estate business, Jim ran for and was elected selectman in 1962. When his father retired as Postmaster and Jim took on the job, he had to resign his selectman’s seat — one may not be both a selectman and a postmaster. Later, he became active in promoting Ted Kennedy’s Island Trust Bill, and, after its defeat, was appointed to the then brand-new Martha’s Vineyard Commission. He was a member of the West Tisbury Conservation Committee, and worked with various conservation groups on the Island.
Jim was married in 1953 to Norma Jean Bettencourt. They had a daughter, Lynne, but the marriage ended in divorce. He married Sylvia Rodgers Carroll in 1959 and adopted Linda, her daughter by a previous marriage. Jim and Sylvia had a son, James, always known as Jamie, who has inherited his father’s flair for the dramatic.
Jim’s long-running, off-again-on-again relationship with Ann Bassett would provide material for a small-town saga. When he began running Misty Meadows Farm, he fell in love with Ann, who managed the riding school and did most of the teaching. They were a couple for five years but had a falling out and then for four years did not speak. In the interim, Jim married Janet Smith Cuetara, but that marriage too fell apart, and Ann and Jim got back together. After their wedding in 1986, Jim had been married four times and Ann, three. The celebratory grounds were decorated by a huge banner reading, “Eat, Drink, and Re-marry.”
Jim loved his family. In addition to Ann, he is survived by his brother John; his children, Lynne Dumas and Linda and Jamie Alley, and his step-children Elizabeth “Lisa” Bassett, Dorothy Whiting (and her husband, Danny), and Grayson Pelletier. He is also survived by grandchildren Dan, Matthew, and Kristopher Dumas, step-grandchildren Will and Morgan Rogers, Cassandra, Tyler, and Fawn Pelletier, and by step-great-grandchildren Scarlet and Lyle.
He was predeceased by his parents and by his brother Albion and his sister, Phyllis Alley Smith.
In addition to his business and political accomplishments, Jim will be remembered for his skill as a raconteur, his sharp wit, and his cynical humor. He loved especially to tell stories about the old days in West Tisbury, tagging many local figures with unflattering nicknames.
Late in life Jim Alley chose to run, unsuccessfully, for selectman again. He ran, not because he wanted the job or needed attention, but because, as he said, “West Tisbury was no longer the warm and friendly place he remembered.”