This Was Then: The gamblers

Losing nickels to the Vineyard’s slot machine syndicate.


Joseph Thaxter, born in Hingham in 1744, grew up sickly and impoverished. He worked on his parents’ meager farm until the age of 19, and planned to become a cooper. But then he bought a winning lottery ticket, and used his substantial proceeds to attend Harvard. After graduating in 1768 (and for a while thereafter selling lottery tickets of his own as a fundraiser for the Revolution), he landed a job as minister of the Congregational Church in Edgartown, where he served as the religious leader of the town for the next half-century.

Gambling — mostly illegal — has been present on the Island in one form or another for centuries. Although it was banned by the early Colonial government, historian Charles Banks found hints of card playing among the early settlers. He writes, “The games of cards known [in Colonial times on the Vineyard] were Primero, Trump, Gresco, Port, Noddy, Gleek, and others not known to the present generation. Whist, or as it was formerly written, Whisk, was not developed till the next century.” The card games of Pedro and Cribbage both became popular on the Island by the turn of the 20th century. We can only assume that at least some of these games involved nontrivial stakes.

There were other popular Vineyard activities, too, on which one could place a quiet bet. Thaxter’s lottery eventually mutated into the ubiquitous Vineyard “numbers racket.” Gambling was reportedly commonplace at the horse track at Girdlestone Park in Oak Bluffs. Then the slot machines arrived. 

The history of slot machines is intertwined with the history of vending machines, which became popular in American cities in the 1890s, dispensing gum, candy, cigars, and soap. “Penny-in-the-slot” or “nickel-in-the-slot” machines could soon be found at county fairs, hotels, drugstores, cigar stores, saloons, and other public places. They were used not only for dispensing products, but also as fortune-telling machines, scales, music boxes, and, inevitably, games of chance. As early as 1893, some cities in Massachusetts were beginning to ban them.

In an attempt to circumvent the bans, a form of slot machine known as the “trade stimulator” became popular at the turn of the 20th century. Users of all ages would insert a coin into these countertop machines, pull a lever, and hope for a winning combination of numbers or symbols to align. But instead of a cash payout, winners would receive cigars, candy, or credit toward other store merchandise, and thereby it remained a legal pastime in many jurisdictions, at least until the law caught up. (One common payout was fruit-flavored gum; the “cherries” and other fruit-themed symbols associated with modern slot machines are vestiges of this tradition.)

For more than 50 years, one such machine was a popular showpiece at the Martha’s Vineyard Museum. A miniature metal bicycle, its coin-operated wheels marked with numbers from 1 to 24, was encased in a wood-and-glass housing. Deidamia Bettencourt recalled in her 1972 booklet, “Come Tour with Me,” “Both wheels are numbered, the slot at the side took nickels, the bell would ring, a lever would be tipped and the wheels spun around. If they both stopped on the same number, the men won a cigar. If the ladies won, they received an ice cream cone.” The device was originally kept in Fred Bunker’s ice cream parlor on Main Street, Edgartown. Sometime after Bunker’s 1896 arrest for liquor sales, the nickel-in-the-slot machine was incorporated into bicycle-enthusiast Leroy Tilton’s newspaper and ice cream store on Main Street, later run by Irving Willoughby, who in turn eventually loaned it to the museum temporarily. (Restored by the museum staff, visitors fed it nickels to watch it operate. Remarking on “the regular whirring of its wheels all summer,” a 1980 Intelligencer noted, “Of all the exhibits in the room, it is the one that is most universally exclaimed over.”) 

Soon, modern slot machines arrived. “I played the slots in Tilton’s drugstore, served by Big Hutch,” recalled John Canha of Vineyard Haven, referring to Kenneth (“Big Hutch”) Hutchinson, a popular clerk at H.L. Tilton’s drugstore in Vineyard Haven (later Yates). “I lost about $5 once, and it bothered me for weeks. It was during the Depression. It was in the mid-’30s.”

By the 1930s, Boston newspapers were full of stories of murder and crime associated with the “growing racket” of the “slot machine syndicate” committed by “slot machine gangs” in Boston and other cities. In 1933, District Attorney Warren Bishop declared a “War on Slot Machines.” “Every nickel in a slot machine during the Depression robs a baby of a glass of milk,” declared one editorialist.

Walter Renear of Vineyard Haven told this story: “Fred Hall ran the general store on Cuttyhunk the summer I worked there. He was a rather profane person, and outspoken in his general dislike for mankind. There was a soft drink hangout that we young people referred to as the ‘Night Club.’ At this location there was a one-armed-bandit (slot machine); there was also another at the Allen House (a Sunday lobster dinner and boarding house). Someone reported these machines to the mainland authorities, and they sent two State Police officers to the Island at night and via the Coast Guard. While one of the officers went to the ‘Night Club,’ the other went to the Allen House. At the Allen House, not seeing any slot machine, the officer asked for a lobster sandwich. After Clarence Allen took the order to the kitchen, he asked the officer if he would be interested in some amusement. The officer responded in the affirmative, whereupon Clarence whipped away a closet curtain and revealed the slot machine. Clarence was actually trying to teach the officer how to operate the machine when the officer called a halt and made his arrest; poor Clarence, as you may have gathered, was not exactly of sound mind, was put in handcuffs and taken to jail in Edgartown. The next morning there was a funeral wreath on Fred Hall’s front door; someone thought he had called the cops. I don’t know, but I think he was capable of it.”

Late one evening in August 1933, the State Police raided the Martha’s Vineyard Country Club in Oak Bluffs. While 150 couples danced, 18 state and local police officers (including eight Vineyard cops) seized two slot machines and roughly $500 of liquor from the club. (Prohibition would not be repealed for another three months.) The club’s manager, Marston Flanders, was arrested and a $500 bail set. (The liquor raid, which followed an undercover operation, also included two Oak Bluffs hotels and three private homes the same night.) Flanders, a Vineyard native and a dropout of Yale’s finance program, soon left the Island to become a resident of West Palm Beach.

But the raid did little to stem the popularity of the machines on Martha’s Vineyard. Four years later, in 1937, after weeks of complaints by residents, police warned proprietors of establishments across town to remove the gambling machines from the Island or face arrest. Some did. Others were visited by plainclothesmen, evidence quietly collected, and search warrants secured. Then, in late July, the State Police staged a fresh raid across Oak Bluffs — this time exclusively for the illicit machines. Led by Oak Bluffs Police Chief Gus Amaral and a contingent of State Troopers, six men were arrested at four locations, and nine slot machines seized. 

Plumber Jack Hughes and his partner Sanford Webb, who held the three-year lease on the bathhouses at the town beach, were arrested. Here at the bathhouses, “the most valuable machine” was taken, according to news reports. An English immigrant, Hughes ran a plumbing shop for many years on Circuit Avenue. (His son, John, helped out at the bathhouses and the attached pavilion, and fondly told stories of his time there up until his passing last fall at the age of 99.) Webb, the 28-year-old son of Dukes County Registrar of Motor Vehicles Harry Webb, worked off-season as a chauffeur and auto mechanic.

At the Oak Bluffs bowling alley, Raul Maciel was arrested. An Azorean immigrant from Fayal who spent much of his life as a Vineyard Haven farmer, Maciel also ran the bowling alleys underneath Cromwell’s hardware store in Vineyard Haven (occupied today by the Green Room).

At the Tivoli Taxi office, Roy Danforth was arrested, and four machines seized. On Oak Bluffs Avenue, William H. Jones and William Wilson were arrested, and three machines seized. Wilson ran a store and billiard hall in Oak Bluffs, but also worked as an employee of Danforth.

“There are no gambling slot machines operating in Dukes County,” the Boston Globe quoted the police after the arrests, in an article subtitled, “Racket Declared at End in Dukes County.”

But of course, they returned. Historian Arthur Railton described the officers’ quarters at the Naval Air Base (today the Martha’s Vineyard Airport) during World War II, which included “a recreation building, complete with slot machines, off-limits, of course, to the ordinary sailor.”

Horserace gambling was legalized in Massachusetts in 1934, and the state lottery was established in 1971. But outside of the state’s three state-sanctioned casinos, slot machines remain illegal in the Commonwealth, unless they are privately held, at least 30 years old, and not used for gambling.


  1. Great story, Chris! Bob Hughes never told me the part about the bathhouse gambling, although he did say his father owned them!

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