The pirates of Long Island

From Captain Kidd to alcohol bootleggers, Long Island was once known as a hotbed for piracy situated between major East Coast ports up until the early 20th century.

Historian and author Bill Bleyer discussed Long Island’s pirate history during a lecture at the Fire Island Lighthouse on July 25, which is part of the Fire Island Lighthouse Preservation Society’s “Two Anniversaries, One Story” lecture series celebrating the 250th anniversary of the United States and the 200th anniversary of the lighthouse.

Bleyer described Long Island of the 17th and 18th centuries as a center for “mom-and-pop smuggling,” for those looking to sneak goods past the port of New York.

In his lecture, Bleyer focused on two famous pirates who visited Long Island: Capt. William Kidd, known for burying treasure on Gardiner’s Island, and Joseph Bradish, who organized a mutiny and also tried to hide stolen goods.

Born in Scotland in 1654, Kidd started out “with a very respectable life,” as the son of a Southern Presbyterian minister, Bleyer said. Kidd moved to New York City and became a privateer, a legal pirate who made his money capturing empty vessels in the Caribbean.

In 1695, Kidd received a royal commission, and The Crown and Kidd agreed to work together in their business ventures. Kidd later set sail on a new ship from the Caribbean, Adventure Galley.

After launching from New York, pressure grew on Kidd since he and his crew would only receive rewards from The Crown if he captured enemy vessels, which he wasn’t finding enough of, Bleyer said.

After not having much luck, Kidd managed to capture the Armenian vessel Quedagh Merchant, which allegedly had French protection and crewmembers, making it a legitimate prize. Soon after capture, though, the crew staged a mutiny against Kidd, and the privateer was seen more as a pirate for capturing a non-legitimate vessel.

Kidd fled to Oyster Bay and hired a lawyer to relay messages to his wife in New York City and officials in Boston to plead his innocence. The royal governor, Lord Bellomont, the same person who granted his privateer license, was in Boston and affirmed his support of Kidd should he come to the city.

On his way to Boston in 1699, Jonathon Gardiner would famously give Kidd permission to bury a chest full of treasure on his island. After arriving in Boston, Kidd would face capture and trial, and the buried treasure on Gardiner’s Island was seized by authorities. Today, a stone marks the spot where Kidd buried his treasure on the island, and a piece of gold- and silver-threaded silk cloth Kidd gifted to Madame Gardiner is still on display.

During his trial, Kidd was not allowed to present evidence that the crew on board the ship he captured was French, with the documentation coming forward years after his guilty verdict and hanging in London in 1701. For three years, Kidd’s body dangled next to the River Thames as a warning against would-be pirates.

Bradish, a squint-eyed pirate with a “nasty” pock-filled face, was born in Cambridge, Mass., in 1672, and unlike Kidd, would initiate a mutiny aboard the Adventure bound for Borneo in 1698 by sailing off when the captain and some crew were offshore.

Upon sailing back from Asia in 1699, Bradish landed in Southampton and was spotted by Lt. Col. Henry Pierson, a local elected official. Bradish lied to the curious Long Islanders about his story, claiming he was en route to Philadelphia from London and needed resupply. Pierson received guns, powder, and a jewel for helping Bradish get sloops and sail to Block Island, where the Adventure sank and its crew fled. Bradish was later captured in Boston and would arrive in London with Kidd and be hanged alongside his fellow pirates.

Over 200 years later, Long Island became a hotbed for a different kind of piracy—bootlegging during the Prohibition Era. Soon after selling alcohol was criminalized in 1920, bootleggers came to a realization.

“New York and all the other states have a three-mile territory limit,” Bleyer said. “So prohibition is only in effect technically out three miles. If you’re 3.1 miles off the shore in international water, you can do whatever you want.”

Entrepreneurs like William McCoy would set up shop smuggling whisky and rum from the Bahamas or Canada, where it was legal, and selling them along “Rum Row” off the coast of Fire Island and New Jersey.

Word spread about McCoy’s business, and soon, fishermen and tavern keepers from Long Island quickly bought every spirit available, making McCoy a $15,000 profit after his first gig, allowing him to expand his business. McCoy also earned a reputation for not watering down drinks, instead selling the “Real McCoy.” With criminals wanting a piece of mom-and-pop bootleggers in the water, McCoy would later install a machine gun on his boat, aiming near anyone suspicious.

In 1923, McCoy was arrested for alleged conspiracy to break the law, but earned a folk hero status. And thanks to some clients, including law enforcement agents and congressmen, he served only nine months in a Washington, D.C., prison, and was allowed to wander around the city during daytime, receiving complimentary meals from his fans. After his release, McCoy moved back to Florida with his brother and revived the boat-building business he had to quit when business was bad a few years earlier.

The Fire Island Lighthouse Preservation Society, with funding by the Robert David Lion Gardiner Foundation, will be hosting more local history lectures at the lighthouse on Saturday nights through August. For more information, visit fireislandlighthouse.com.