Ahoy Matey, Did You Know Pirates Once Sailed Along the Hudson?

September 19 is “Talk Like a Pirate Day,” but once upon a time, the Valley had its own piratical heyday.


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Most everyone celebrating “Talk Like a Pirate Day” today will do so with a Johnny Depp-like saunter in their step and myriad inflected “yars” throughout the day. Instead, how about talking like a post-Civil War knickerbocker?

While the idea of pirates tends to conjure up images of the Caribbean and large merchant vessels, the Triangle Trade and perhaps even a modern-day set Tom Hanks film, the late 19th Century was actually a highly active time of piracy up and down American rivers. The Hudson River, intrinsic to New York City trade, was no exception.

Most of these “pirates” were street gangs who would pilfer cargo and other goods from ships docked along the riverfront, and occasionally those in open water. Groups such as the Hook Gang and Patsey Conroy Gang ransacked New York City’s ports from about 1866-1877. The groups were professional, well organized, and consisted chiefly of Irish-Americans and Irish immigrants.

The most prominent group, however, was the Charlton Street Gang, which peaked in 1869 under the leadership of folklore villain Sadie “the Goat” Farrell. According to legend, Saddie was a mugger in New York’s Fourth Ward with the modus operandi of charging and head-butting a man in the stomach while her accomplice robbed him, who lost her ear in a feud with (the most likely real) six-foot female bouncer Gallus Mag. Witnessing members of the Charlton Street Gang fail to forcibly board a sloop, she offered her services and was made the group’s leader.

Within days they successfully hijacked their own boat, raised a Jolly Roger flag, and began a summer of pillaging villages and farm houses up and down the Hudson, traveling as far as Poughkeepsie and even Albany. Saddie the Goat led robberies of several area mansions and orchestrated a number of kidnappings, holding men, women, and children for ransom. She is even reported to have forced several male captives to “walk the plank.”

The Charlton Street Gang had a very profitable summer, stashing booty along the banks of the Hudson to slowly and inconspicuously fence at later dates. Following a number of murders, however, locals formed a vigilante group and began fighting back, firing on the gang and killing several of its members. The group, Saddie supposedly included, abandoned their boat and returned to New York City where the “Queen of the Waterfront” and her gang returned to street crime until the group's dissolution some time around the end of the decade.

River Piracy in New York dried up after 1876, when NYC Police Sergeant George W. Gastlin put together a “steamboat squad” — really — of armed policemen in an organized crackdown. By the following year, the gangs had mostly disbanded or been arrested.

This year, instead of peppering burrito lunch orders with a hardy “yo-ho,” consider having dinner on the riverfront, renting Gangs of New York, and talking like Leonardo DiCaprio.

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