Prohibition days in Saugerties

Legs Diamond

Legs Diamond

In 1929, Prohibition-era gangster Jack “Legs” Diamond bought a house in Acra, in Greene County, just west of Cairo. He moved in with his wife and his mistress, each of whom was wildly jealous of the other. They walked around the house armed, just waiting for the other to try something. But unbeknownst to them, neither of them may have been the other’s biggest problem.

Legs was sneaking out on both of them, to visit a girlfriend in Saugerties, on Montross St.— perhaps when he came to town to buy meat at Rinaldi’s Meat Market, at the foot of Partition St. The girlfriend was Myrtle Whitaker, and she survived the wild days to become quite a local fixture. Younger folks like Steve Dawson, growing up on MacDonald St. in the ’60s and ’70s, remember her well. And Don Hackett, who bought her house from her in 1989, remembers her as “a very sweet woman.” She died in 1995.

The Roaring Twenties were a roaring old time in Ulster County, thanks in great part to Legs Diamond. He had an aqueduct constructed under the streets of Kingston: a beer aqueduct, running from his brewery at Barmann and South Clinton avenues in Kingston down to the river, where barrels of beer were filled and loaded onto barges. One rumor has it that Judge Joseph Force Crater, who stepped out of a night spot in midtown Manhattan and was never seen again, may have been buried in Legs Diamond’s brewery.


Ulster County had its own Flying Squad of Prohibition agents, like the one made famous by Eliot Ness in Chicago, and newspapers of the day carried stories about the agents busting up a still in Glasco, or making a raid on a widow in Centerville who was selling booze out of her kitchen. There doesn’t seem to be much about raids on any of Legs Diamond’s major operations, so it may be that these guys weren’t completely untouchable.

There were no shortage of Legs Diamond sightings in Saugerties, even beyond the house on Montross Street. He was said to have tossed back more than a few at the Mount Marion Inn (rumor has it he may have been a part-owner), and at a speakeasy on Rt. 32 near the site of the current Howard Johnson’s.

Saugerties certainly had its share of speakeasies. The venerable Exchange Hotel, whose roots go back to the mid-19th century, was owned in the 1920s by Glen Robinson. Robinson saw no reason to discontinue a generations-old tradition of serving fine (and plain) libations just because an aberrant law said that they should, and as a result it was raided with some regularity. Its head was bloodied but unbowed, and it remains proudly on the corner of Main and Partition, a Saugerties landmark.

Frank’s Hunting Lodge served beer and pizza to more than one generation of Saugertiesians well into the 21st century, before finally giving way to progress, first in the form of Mirabella’s. Currently, after that establishment moved to its new quarters across the alley, it’s between functions. But back in the twenties, a speakeasy stood on that corner, and it, too, saw its share of raids.

Joe Zmiyarch recalls his grandfather, who tended bar at a couple of different speakeasies back in Prohibition days. One was at Brassy Point, off Dock St. The other was at 11 Jane St., which in more recent times was home to Debra Lavaggi’s Laughing Bear Batik. One newspaper item from 1927 describes a raid by Prohibition agents who padlocked the back door at 11 Jane. Why only the back door? Well, apparently they had raided the place a couple of weeks earlier and padlocked the front door, but had missed the back. And it’s possible that all of the padlocking was an exercise in futility. The story goes that there were secret tunnels leading into and out of the basement, which connected to another speakeasy on Partition St. If one establishment was raided, patrons could use the tunnel to escape to the other, where they could go on partying.

The elder Zmiyarch was, according to his son, ideally suited for the job of bartender at a rowdy speakeasy. He stood 6’ 6”, and supplemented his income from the mill and illicit bartending by prizefighting in local club fights. He was undefeated except for one bout in which his opponent floored him with a rabbit punch. A rematch was scheduled, but the guy never showed up. It’s easy to understand why not.

There were other ways to make money off of Prohibition. One local garage owner made an arrangement with a certain somebody— it was never exactly made explicit who that somebody was, but it was pretty well understood that the individual’s name had “Legs” somewhere in it. The garage owner was to leave his truck by a crossroads near Tannersville, with the key in the ignition— or the crank under the seat, if it was an older truck. The next day, the truck would be there with an envelope full of money. Or perhaps, if there’d been a mishap, just the envelope, with enough money to buy a new truck.

Perhaps it might be easier to list the establishments that weren’t speakeasies in the twenties. Not quite every tavern or eatery in Saugerties succumbed to the temptation of Prohibition bucks. Henry Wilgus in High Woods ran his general store and held off selling beer until repeal. The Crystal Lake had chocolate parties. Then there was the place at 253 Main St., now the Old Dutch Ale House, with its beautiful mural over the bar of Saugerties in colonial days. But we’re not going back that far. Only until the day that Prohibition ended, when the tavern opened, innocent and legal. But if it was really so innocent and legal, how was it that the day the Volstead Act was repealed, it was completely set up and ready to go, with a full complement of liquor, beer, taps and fittings?