Greenport - Recently, New York City mayor Michael Bloomberg signed into law a bill effective May 23, 2011, which will prohibit smoking in and on all New York City parks, beaches, boardwalks, pedestrian plazas and other public spaces. Smokers and lobbyists against the legislation have been up in arms, claiming that the law meddles in the private lives of the public.

Bill Claudio, Jr., the present owner of Claudio's, and the infamous trap door. (Hamptons.com File)

In light of this controversy, I'd like to take a look back at another controversial law which most felt interfered in the private lives of the public: The 18th Amendment in conjunction with the Volstead Act. Commonly called Prohibition, the law went into effect at 12 midnight on January 17, 1920 and lasted 13 years. The law made it illegal to produce, import or consume alcoholic beverages on U.S. soil, and while Mayor Bloomberg's NYC cigarette laws have not gone quite as far as the Volstead Act, is it easy to see how the latter is reminiscent of the former.

In the case of both prohibition, and Mayor Bloomberg's first piece of smoking legislation, which prohibited smoking in bars and restaurants, citizens continued to partake in use of the illegal substances in the months following the law's passage. It is assumed that this same thing will occur in New York City after May 23 of this year.

Eventually though, in the case of prohibition, which outlawed a substance in its entirety, the lackadaisical enforcement of the law came to an end, and born out of prohibition, came a booming industry of rum running and bootlegging across the United States. As a result of its close proximity to New York City, access to water, and isolation, Eastern Long Island became a hub for the illegal trade.

Opportunists from all over the world recognized prohibition's potential as a moneymaker, and flocked to enter the trade. Cases of rum were purchased from the West Indies and Caribbean, while whiskey and other liquors were purchased in Canada and Europe. Ships would then float three miles off shore just outside of U.S. waters at what they called the "rum line," and wait for Long Island fisherman, lobstermen and whalers to arrive, pick up the goods and transfer them back to land. In 1924, an act of Congress extended the rum line to 12 miles out.

This new breed of local outlaws who helped smuggle in the illegal booze were one of the contributing factors that led to the success of bootlegging on Eastern Long Island. Their knowledge of local waterways was unparalleled by the Coast Guard, and they consistently outmaneuvered those looking to stop them. Oftentimes they brought in the goods under the cover of a heavy rain or thick fog, and would sneak cases of alcohol in through secret passageways and storage rooms.

Once the alcohol was on land, it was hidden in secret compartments in trucks and cars, and transported to NYC for distribution. After a few years, rum running became more dangerous, as gangsters like Dutch Schultz began hijacking the alcohol from other rum runners. The king pin of bootlegging on Long Island, Schultz was a force to be reckoned with, and those who crossed him did not live to tell the tale.

Greenport thrived during prohibition, and Claudio's Restaurant, the oldest family owned and run restaurant in the country found its way into the illegal spirits business, as the downstairs of the building became a fine French restaurant while the upstairs served as a speakeasy.

Captain William "The Real" McCoy. (Courtesy Photo: Outlanderssc)

A dumbwaiter to the downstairs allowed diners to get in on the action by sipping on "water glasses." Claudio's sat on stilts and boats would race into the harbor and head underneath the building where the alcohol was offloaded through a trap door. One trap door still exists to this day. Claudio's ceased participating in rum running activities in 1926 after a car transporting liquor to New York City was hijacked and and the driver shot.

Montauk also played a huge role in the bootlegging business. Perhaps due to the fact that it, like Greenport, is very far east and isolated. Also like Greenport, Montauk was full of skilled sailors who welcomed a way to put extra money in their pockets. These sailors would drift at the rum line and await a fleet of Nova Scotian, English or Cuban ships to get the goods.

One of the best-known liquor boats was the Arethusa, captained by William or Bill McCoy. McCoy gained a reputation for carrying good, non-watered down booze for a good price and as a result became known as "The Real McCoy." Some credit the Bill McCoy/prohibition story as the creditor of the popular phrase, which we still use to this day.

In Montauk, the Wyandannee Hotel was a popular storage place for the booze, while the Island Club, a monumental nightclub and casino on Star Island was the most popular local speakeasy. Many notable guests visited the Island club including Jimmy Walker, Ernest Hemingway and John Barrymore.

In Riverhead, Tweed's Restaurant and Buffalo Bar, which traces its roots back to 1886 still stocks traditional liquor brands such as Plymouth Gin, Gordon's, Cutty Sark and Four Roses. During Prohibition, liquor was moved through a series of dumbwaiters and trap doors into the restaurant.

Prohibition, or "The Noble Experiment" as it was later called was repealed and completely abolished by the government on December 5, 1933, as a result of the crime and corruption it causes across the country. Recently, with smoking laws infiltrating New York City, Prohibition era drinks and style have been revived, especially in New York City. Many faux speakeasies have been built to provide drinkers will the proper venue to enjoy their classic cocktails. While the rum running businesses heyday is long past, the legacy left behind by the bootleggers and participating restaurants and bars have left their mark on the East End to this day.