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Looking Back: The Story of the Casino in Montauk

Wild nights with rich socialites gambling in Montauk.

It’s a warm summer night.

It’s after dinner and your car is pulling up to a guardhouse. The attendant looks into the vehicle and sees everyone is in swank black tie attire and waves you in. As the valet opens the doors to your car you smile noticing the long line of limos off to the side. Before you walk through the large double doors as you take one last look at the stars, the huge yachts, and the brand new docks so nearby. As you enter the luxurious edifice you hear the band playing live dance music, you see huge gambling tables. Dice tables for craps, blackjack tables, huge roulette wheels spinning, as people place their bets. The bar is eight back with black tie dressed men and glamorous evening gowned women. And on the dance floor the dancing flows in step to the live music with cigarette and cigar smoke hovering over it all. You hear the sounds of gambling winners screaming as their card come in they number hits or their dice bring up the lucky numbers.

If it sounds like Monte Carlo, it was meant to, but it is Montauk in the 1920s at the Star Island Casino opened and constructed by the Montauk legend Carl Fisher. It was located next door to the Montauk Yacht Club and near where the Star Island Marina is today not to far from the United States Coast Guard Station, all on Star Island.

Mr. Fisher personally supervised the wine list, the spirits, and even the music. The amazing thing was that the whole scene with 200 to 300 nightly guests, with black tie required, was all illegal! Yet even one night New York City Mayor Jimmy Walker had to be spirited away quickly before a raid by the Town of East Hampton Police arrived. (Which at that time was done rarely and friendly). A senior fishing gentleman friend of mine who went to the casino said, “It was wild, with beautiful famous glamorous socialites, including Vanderbilt’s, Astor’s and Whitney’s. All enjoying their visit to Montauk, for gambling. The jewelry was unbelievable. All I did was dance and drink, I never gambled. The buffet was amazing and free.”

The aftermath and effects of the stock market crash of 1929 eventually bankrupted Mr. Fisher and his various properties ended up into the hands of banks and smart investors. The Star Island Casino was purchased and ran by a syndicate who also owned casinos in Miami and Cuba. The casino survived the hurricane of 1938 and it remained in their control until a final New York State Police raid and its consequences closed down the operation permanently in the very late 1940’s. The building for a while was converted to house employees of the Montauk Yacht Club and eventually was destroyed by fire although the guard house that was at the entrance of the road still exists out there by Star Island Marina and The Montauk Yacht Club.

The visionary Carl Fisher who blasted open Montauk Lake to the Block Island Sound and then dredged the lake to create a harbor enabling deep keeled sailing yachts of the time to enter and tie up at the casino only tasted the tip of the success . His whole concept of making Montauk a resort town besides just being one of the great fishing villages in the United States is now a reality. His vision was for the beautiful people to go to Miami in the winter and Montauk in the summer.

So in the roaring twenties during prohibition, in the era of the “speak easies “ before World War Two, the bath tub gin was flowing in Montauk, The Hamlet was the destination of the late night social crowd of Southampton, East Hampton and other nearby towns and villages. The drive down the Napeaque stretch on Route 27 even then was an adventure. As my senior sailing buddy recalled, “There was no Long Island Expressway back then so it wasn’t a weekend crowd. Very rich people came out and stayed all summer arriving with huge trunks either off private railroad cars or yachts. And at night after regal dinners, at the clubs or mansions, the drive to Montauk was an adventure, in opened aired limos or regular cars. Everyone knew everyone .” So in a way Montauk was like Monte Carlo.

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