Crooked little Gay Street looks like the perfect place to open a speakeasy.

So it’s hardly a surprise to learn that one existed here in the 1920s.

Called the Pirate’s Den, the illegal bar was run out of number 12, a Federal-style house built in 1827—back when Gay Street was just a slender stable alley in up-and-coming Greenwich Village.

See the metal arch placed in front of the building? It supposedly marked the bar’s basement entrance.

Located near other Village speakeasies, such as Julius’ on West 10th Street and the Red Head on Sixth Avenue, the Pirate’s Den was more of a tourist trap than a place for locals.

“[It featured] clanking chains, clashing cutlasses, ship’s lanterns, and patch-eyed buccaneer waiters,” writes George Chauncey in his book Gay New York.

Twelve Gay Street isn’t only known for its liquor joint rep. After the Pirate’s Den closed down, Mayor Jimmy Walker, a notorious partier and playboy, moved his showgirl mistress here, turning the house into kind of a second Mayoral home.

Could he be the mysterious figure in a top hat and tails, dubbed the Gay Street Phantom, who is said to creep around the stairs at night?

“The historic Gay St. property, on the corner of Waverly Place, is rumored to be inhabited by a restless spirit who walks the creaking floorboards at night,” states a 2009 New York Daily News article.

[Top photo: Streeteasy; bottom, NYPL Digital Gallery]

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Tags: 12 Gay Street, alleys of New York City, Gay Street NYC, Gay Street West Village, Greenwich Village bars, Mayor Jimmy Walker, New York during Prohibition, New York speakeasies, Speakeasies of Greenwich Village