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Cairo and the Time 
of Prohibition

by Robert Uzzilia
Cairo Town Historian

Originally published in Daily Mail November 2, 2003

For many people in the town of Cairo during the 1920’s, autumn in the Northern Catskills meant crisp mornings, colorful leaves, barn dances, hayrides and apple picking. For others it meant business. Big Business. 

The Prohibition movement in this country, which began with just a handful of states in the mid 19th century, had culminated with a constitutional amendment and the attempt at a dry nation, beginning January 1, 1919. This prompted the establishment of an illegal industry, in which a handful of powerful men, vied for control of massive profits and prestige. 

One such man was Jack “Legs” Diamond, a former bodyguard for powerful labor gangster Arnold Rothstein. Diamond had been run out of New York City for a number of illegal activities and found a haven in the rolling hills of Greene County. Here he felt powerful, in control and yet respected. He purchased a home on route 23 (then called the Mohican Trail) in Acra with his wife Alice. Greene County would eventually become a channel for booze distribution from Canada to New York City. While statistics on this and other illegal trade naturally don’t exist, suffice it to say local demand existed, as well as downstate, and not everyone wanted to run the likes of Diamond out. Locals now reveal that he provided much economic stimulus, at a time when many were struggling. Diamond was known to have assisted needy families at Thanksgiving, anonymously purchasing turkeys at the local “A&P,” attending Sunday Chicken dinners at the Traveller’s Rest (behind present-day Masonic Temple). He contributed to the building of St. Edmund’s Chapel in Acra, assisted with several delinquent mortgages and routinely tossed coins to village children. He once tipped Kiskatom farmer Matt Story fifty dollars just for changing a flat tire. 

So, despite his ties to an illicit bootleg operation he was viewed by the public as a “champion against the dries,” according to Dr. Gary Levine. In his 1995 book, “Anatomy of a Gangster.” Levine also described gangsters in general as “self-reliant, diligent, successful and romantic individualists who were always persecuted by the establishment.” So it is no surprise that as bootleg whiskey was produced and distributed locally during this colorful period, that dichotomous anti-hero figures like Diamond were in subtle ways, protected by the locals. The trucking firm of Fred Spohler would sometimes discover a vehicle was missing but would mysteriously re-appear the next morning. They assumed it was Diamond, or Shiffer, one of his many aliases. Nothing was said, just a simple notation in the ledger. For farmers, the normal apple yield would have been partially wasted if the local demand for applejack dried up. Hence, stills could be found all over the back woods of Cairo, in cellars and even an occasional bathtub. It would be trucked to local establishments at off hours and stored in unmarked crates. The drinking would go on if you knew where to go and who to ask. The term “speakeasy” most likely originated from the idea of keeping your voice down when asking for liquor. 

Local law enforcement tried their best to keep things under control. They assisted in several raids to Diamond’s home and occasionally busted up a still in cooperation with state officials, but it would take years of evidence gathering, subpoenas and shootings from rivals to finally bust up Diamond’s stronghold and the bad publicity was taking its toll on a town that then thrived on summer tourism. Eventually even the local Chamber of Commerce made a formal statement condemning the illegal trade and appealed for the public’s help in eradicating the venom. A locally formed chapter of the WCTU (Women’s Christian Temperance Union) assisted by illustrating the evils of intoxicating liquor and praying for those tortured souls who were in its grasp. 

With or without liquor, however, a favorite escape of the pressures of “modern life” was dancing to live music. While Paul Whiteman’s orchestra, Al Jolson and others entertained the masses on the ever-expanding medium of radio, it was live bands providing the fox trots and Charlestons at local dance halls. One such establishment was called “The Ritz,” a converted barn located on the Finch farm (near present-day Stewart’s Shoppe) offered dining and dancing. Nearby was the Aratoga Inn, run by Jimmy Wynne, who offered six beautiful dancing girls as part of the entertainment. Another popular nite spot for those on either side of the liquor issue was Baldwin’s Hotel in Purling which sported a nicely polished dance floor for its patrons. Other resorts, like the High View House and Acra Casino Boarding House would add dance halls for their guests.

When Prohibition finally ended in the early 1930’s and the gang of “Legs” Diamond had been all but eliminated, a violent but fascinating period faded into the obscurity of legend. Decades later though, the echoes of shots fired still reverberate in this rural Catskill Mountain town.

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