James Flight Alley, 81, former West Tisbury postmaster and selectman, conservationist and life-long Democrat, real estate broker, horse dealer, farmer, new- and used-car salesman, and owner, with his brother, John, and his late sister, Phyllis Alley Smith, of Alley’s General Store from 1961 to 1981, died in West Tisbury on Wednesday after a long bout with cancer.

Except for a youthful year-long foray to California with a high school classmate, he had lived all of his life in West Tisbury and loved it with a passion. It was this passion that fueled an attempted return to politics in his mid-70s. He was dismayed by the direction he felt his town was taking, losing the character of his early years as a friendly, gentle community. He ran again for selectman in 2006 and was only narrowly defeated.

Jim (or “James” or “Jimmy,” as he was variously called) was born March 8, 1932, at the Martha’s Vineyard Hospital in Oak Bluffs, a son of Albion A. and Mary Ann Flight Alley. He was a graduate of the West Tisbury School and Tisbury High School, class of 1949. There he was active in school plays, developing an ability to speak before the public that would serve him in good stead in later years in politics. Indeed, his ability as a public speaker earned him the nickname “Deacon.” His mother always insisted he would have had a fine future as a preacher.

A lifelong enthusiasm for sports began in his high school years. He played basketball and softball and joined the skeet-shooting club in West Tisbury started by the late Nelson Bryant Sr. He was such a fine basketball player that his coach begged his father to let him out of after-school work at the family store so he could attend practices. His father’s terse reply was that he needed him to “dribble” groceries onto his store shelves. His fondness for softball continued long after his school days and he would often play on pick-up teams at Veterans’ Memorial Park in Vineyard Haven. Although he was never a real enthusiast for water sports, he would occasionally fish and after he and his siblings had sold the store he bought a small boat on which to make occasional fishing expeditions. After a shark thrust its head up near the boat in the Middle Ground off West Chop he sold the boat.

Much later in life he became a golfer, playing regularly at Farm Neck with the Quahaugers, a group that consisted of Ben Moore, Tess Bramhall and the late Stan Murphy. He also played every noon with the “Loony Noonies,” which consisted of the late Norman Friedman, Ralph and the late Berry Franklin and Bobby Phillips. As a golfer he was noted for the strength of his swing, which often sent the golf ball flying off into the woods. Even into early winter he and his golfing companions would keep on playing.

Jimmy Alley at home in West Tisbury.

“He was delightful to play golf with,” Tess Bramhall remembers. “It’s not often that a golfer is willing to help someone else with their game, but Jim always was. He was a very gentle soul.”

His interest in horses began when he was a teenager and he helped look after two draft horses that Harry West kept in a barn on Music street on what is today the Coyne property. He and a friend would dutifully feed the horses after school, but then at night they would ride them, leading Mr. West to wonder why his work horses were so tired every morning.

After his graduation from high school he moved to California where he and his companion pumped gas and worked in a ceramics factory by day and sang in bars at night, passing the hat for donations. He soon returned to the Island and worked in his father’s store and as a bartender at the Boston House in Oak Bluffs in the evening. In 1953 he married Norma Jean Bettencourt of Vineyard Haven. Both were members of the Martha’s Vineyard Young People’s Club, of which Jim was president. The young couple made their home in Vineyard Haven and became the parents of a daughter, Lynne. But the marriage was short-lived and in 1959 Jim married Sylvia Rodgers Carroll of Vineyard Haven, a co-worker at the Boston House. Soon after that he began selling cars, taking a part-time job with the late Al West who had a car dealership at the airport. With little runway traffic in those days, Jim would let customers test-drive cars on the runway.

In 1962 he entered politics and was elected a West Tisbury selectman. He was also a police officer at the time and had a red police siren attached to the top of his car, his son Jamie remembers. In 1965, when Jim’s father, Albion Alley, who had been postmaster for 21 years, decided to retire, Jim took on that job. Federal government regulations forced him to give up his selectman’s post just before the expiration of his term. By then he had joined his father in the real estate business. In 1988 they opened a car wash and a laundromat beside Alley’s General Store. Three years earlier Albion Alley had bought the Vineyard Bowling Center in Vineyard Haven, renamed it Alley’s Alley and Jim began to run it at night.

He and his family had moved to New Lane in West Tisbury to a house they called Misty Meadows because of the mists over Doan’s field behind their property. By then there were two children, Linda and James Jr., along with the first of Jim’s old cars, a Model A called Ebenezer, and some horses. Linda got her first horse, Major when she was 10. Young Jamie, at four, had a pony named Chico. Their ever enterprising father soon opened a tack shop on the property for other horse owners. He began buying horses to sell and before long he was riding them, too.

In 1973, with the late William M. Honey, he bought 40 acres abutting the State Forest on Old County road and began a horse farm. This new Misty Meadows, as they called it, had a full program of riding instruction, trail riding, horse boarding and even horse breeding. There were outdoor rings, including a dressage ring. Soon Jim was making off-Island trips to buy horses for Misty Meadows and other horses to sell. Ever since his boyhood days, when he had ridden the West draft horses at night on Music street and watched Lone Ranger and Gene Autry movies, he had been enamored of horses. He soon began playing the cowboy part, wearing cowboy boots and sporting a cowboy hat.

Ann Bassett and Jimmy Alley. — Peter Simon

The 1970s were also an era when Jim expended a great deal of time and energy seeking to protect the Vineyard he loved. It was in 1972 that Senator Edward M. Kennedy proposed the establishment of the Islands Trust to preserve the Vineyard and Nantucket from over-development in the same way that his brother, President John F. Kennedy, had created the Cape Cod National Seashore to protect Cape Cod. Antagonism on the Vineyard to Senator Kennedy’s proposal was fierce among developers and workmen in the building trades, and wealthy landowners who feared that the property they owned would be taken away from them by the federal government or that sale of it would be prohibited if it were in an environmentally delicate location. As a staunch Democrat and dedicated Vineyard conservationist, Jim Alley immediately joined the Kennedy forces, meeting frequently with the senator and his staff members. Knowing as many Islanders and off-Islanders as he did as West Tisbury postmaster (a job he kept until 1982) and as a storekeeper, he was in a position to “talk up” the so-called Kennedy Bill positively and point out the good it could do for the Vineyard. When it failed to be enacted, the Martha’s Vineyard Commission was formed in 1974 to do what it could to prevent egregious overdevelopment. Jim was appointed as the West Tisbury representative. He also became a member of the West Tisbury Conservation Commission.

During the 1970s the Martha’s Vineyard Airport Commission wanted to expand the airport to allow jet planes to land. This involved changing the contour of the West Tisbury-Edgartown road. This was another controversy that captured the attention of conservationist Jim Alley.

Also in the 1970s he and Bill Honey added Scottish Highland cattle to their livestock at Misty Meadows. Meanwhile his second marriage had foundered, and in 1980 he married Janet Cuetara of West Tisbury, a fellow horse enthusiast. Together they had a log cabin constructed on Old County road not far from the Misty Meadows property.

But that marriage, too, ended in divorce. In 1986 he married Ann Bassett of West Tisbury, another horse enthusiast who had been the manager at Misty Meadows. About this time, he began to quip about having a bumper sticker printed saying “Honk if you’ve ever been married to Jim Alley.” The newlyweds frequently went off-Island on horse-buying expeditions. They became particularly fond of acquiring Missouri Fox Trotters, horses with an especially smooth gait. They frequently did their horse-buying from the late Ronni Peakes, a Vineyard Haven man who had moved to Milbury, Mass. Jim often told inviting stories of the horses he was trying to sell. “This one belonged to a little old lady who used to ride it bareback to the mailbox.”

After his retirement from the store and the post office and his sale of Misty Meadows, Jim began selling secondhand cars at the Woodland Garden Center in Vineyard Haven. He told the same sorts of tall tales about the cars he was selling.

Jim was a fine storyteller with an outstanding sense of humor, his friends and family recall. He was an ever-supportive employer, according to those who worked for him. He was remarkable in the way he never forgot a customer’s name, longtime Alley’s General Store patrons remember. Above all, they unanimously agree, he was a savvy businessman, a hard worker, a charmer of young and old, and a resident of West Tisbury and the Vineyard who worked tirelessly for the betterment of both.

He is survived by his wife Ann Bassett and his brother, John of West Tisbury; three children, Lynne Dumas of Centreville, and Linda Alley and James N. Alley Jr., both of West Tisbury; three stepchildren, Lisa Bassett and Dorothy Whiting of West Tisbury and Grayson Pelletier of Edgartown; three grandchildren, Matthew, Daniel and Kristopher Dumas of Centreville and three step-grandchildren, Cassandra, Fawn and Tyler Pelletier of Edgartown.

A graveside service will be held next Friday, May 24, at 11 a.m. at the West Tisbury Cemetery.

In lieu of flowers, the family requests that contributions be made to Hospice of Martha’s Vineyard, PO Box 1748 Vineyard Haven, MA 02568, Tri-Town Ambulance of Martha’s Vineyard, PO Box 340, Chilmark, MA 02535, or the Visiting Nursing Association of Martha’s Vineyard, 29 Breakdown Lane, Vineyard Haven, MA 02568.