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When Montauk Was a Bootlegger’s Paradise

August 15, 2025
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When Montauk Was a Bootlegger’s Paradise
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Good morning. It’s Friday. Today we’ll look at Prohibition-era bootleggers on Long Island and the rapper who is a great-grandson of a lawyer who defended them.

What if a crooked state trooper hadn’t had to report the loss of his uniform, his badge and his gun — filched by Prohibition-era bootleggers who beat him up?

In that case, a Brooklyn lawyer named Rufus Perry Jr. probably would not have been hired by a rival bootlegging crew that was in league with the trooper.

And the rapper Freedom Williams wouldn’t have had a very personal reason to go to an exhibition about Prohibition-era rumrunning on Long Island, 100 miles from where Perry lived in Crown Heights and where Williams lives now.

Perry, Williams’s great-grandfather, is one of nine people highlighted in the Montauk Historical Society’s exhibition “How Dry We Weren’t.” It makes the case that Montauk, before the surfers and the expensive houses in the dunes and the status-conscious New Yorkers, was rife with rumrunning.


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The post When Montauk Was a Bootlegger’s Paradise appeared first on New York Times.

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