Corlears Hook was once a middle-class neighborhood on the Lower East Side of Manhattan which in the 1820’s began its descent into a den of crime, vice and sin. It was once a Native American Settlement and then an industrious shipyard, the neighborhood was about to become a red light district filled with violence and thievery.

The Brooklyn Daily Eagle would describe it as “the Five Points of its day and the inhabitants were the vilest of the vile, male and female.”

During the early part of the 1800’s an influx of poor German and Irish immigrants who were looking for work and housing paved the way for cheap and poorly built wooden tenement buildings, that became crowded with sometimes 10 – 15 people per room. Describing Corlear’s Hook, the New York Times would say, “…many daring deeds of villany have been consummated in its malarious slums…”

With sailors indulging in the numerous saloons along the waterfront, prostitution became prevalent. Corlears Hook was home to some of the most notorious streets in Manhattan’s streets, Water Street, Cherry Street & Walnut Street. All of which had their own characteristics, Walnut Street was essentially a row of brothels where the women of the night plied their trade and would administer “knock out drops” to unsuspected customers, who would wake up later minus their possessions. Water Street where the Wickedest Man in New York, John Allen ran his saloon and Kit Burns had his infamous Sportsman’s Hall or the Rat Pit as it was known. On Cherry Street was Tommy Hadden’s Shanghai Hotel, where sailors and unsuspecting victims would have a knock out drop or two put in their drink and wake up far out to sea after Hadden had fulfilled an order from a ships captain who was in quick need of some sailors.

However Corlear’s Hook was known for its gangs of river pirates, who would terrorize its waterfront and the shipping companies that used it, the river pirate gangs made Corlear’s Hook one of the most bloody area’s in Manhattan. The river pirates would fight, rob, and murder anyone, looting of arriving ships was common, these colorful gangs who left a trail of dead bodies in their path.

Probably the most dominant river pirate gang of that era was the Patsey Conroy Gang who were based in the Corlears Hook section of the Fourth Ward. Conroy formed the gang in the 1870s. The Conroy Gang consisted of many experienced criminals from the area Denny Brady, Larry Griffin, Pugsey Hurley, Bum Mahoney, Kid Shanahan & Johnny Dobbs, many of which would remain high profile criminals throughout the late 1800’s, Larry Griffin & Denny Brady would become joint leaders of the Conroy gang also.

The Charleton Street Gang were one of the earliest gangs of river pirates, they were led by a semi-folklore character Sadie “The Goat” Farrell, though she was semi-folklorish there are many stories and accounts about her. The gang began raiding cargo ships in the North River of New York Harbor, overtime the dockyards became so well protected the gang had to start moving further to find ships to rob. The gang moved to the Hudson River, Harlem River and as far away as Albany. Under Farrell they came up with new tactics, taking men, women and children hostage for ransom. But soon the people who lived along the rivers formed vigilante groups to combat the pirates, they would attack the pirates as they moved up the rivers. After a while the gang were resigned to the fact that piracy wasnt as profitable and disbanded.

Under Pier 57 was the hangout of the murderous Short Tails Gang. The Short Tails were a particularly nasty gang of criminals who terrorized the Lower East Side and the docks of Corlears Hook. By the 1910s, this sinister gang had been absorbed into other street gangs. They often committed crimes on vessels along the water front. The unfortunate members of the Young Men’s Cathedral Association learned this the hard way during an river outing in 1886. “Some members of a notorious gang, calling themselves the Short Tails, smuggled themselves on the boat, got drunk and began to fight.”

The gang was certainly no match for the police. One officer in the 1880s, avenging a friend killed by a Short Tail, stormed right into their headquarters “without club or firearm of any kind” and personally throttled a great number of them, “grabbing two of the more notorious by their coat collars” and dragging them to jail.

The Daybreak Boys were probably the greatest of the East River pirate gangs, they were known for sabotaging and robbing boats in early morning hours, they are rumored to be responsible for up to 40 murders in a two year period. The Hook Gang were the last of the river pirate gangs. They number about 100 and were known to hijack ships while blocking off streets leading to the docks.  With the newly formed Steamboat Police Squad in 1876, the Hook Gang and the era of river pirates came to an end.


Carl Sifakis – Encyclopedia of American Crime
Herbert Asbury – The Gangs of New York
Legends of America
Old Salt Blog

Owen Forsyth

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