John T. Diamond, also known as Jack, was familiar to his friends as “Legs” for his dancing prowess. It is unclear if his enemies called him that and got away with it.

Diamond was one of the biggest whiskey and beer bootleggers in the Northeast of the Prohibition Era. Biographies have been written about him. And he was cold to the point of freezing, like his last name. Depending on the source, more than 25 murders can be laid at his feet.

Diamond lived in Cairo for a time and became a local hero. They called him “Champion Against the Drys” for his obsessive defiance of Prohibition. One of his final addresses was a cell in the Greene County Jail.

Now, the old Greene County Jail on Bridge Street in Catskill is passing into history, just as Jack T. “Legs” Diamond passed into legend. And not everyone is happy about it.

Demolition of the 112-year-old jail is bittersweet. Cost comparisons show it would be $3 million more to tear it down than to rebuild it. So this was the fiscally responsible path to take for county taxpayers already footing the bill for the county’s new jail in Coxsackie.

On the other hand, the demolition represents a historical loss to the community. The jail and sheriff’s office, also scheduled to be razed, were integral components of an architectural group at the corner of Main Street and Bridge Street: The Greene County Courthouse, the jail, the sheriff’s office, the Catskill Public Library and the banks were all built in the early 1900s.

They expressed an architectural theme important for the Main Street Historic District and soon this large section will be gone. Plans for the new open space are not finalized, but word is it will become a parking lot. Tons of brick-and-mortar history are going to be trucked away forever. A parking lot doesn’t seem to be a fitting tribute to what has been lost. Besides, what would Legs Diamond think?

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Johnson Newspapers 7.1


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