Rewind: January 15, 2024 – “Tales from Warren County’s Bootleg Trail”

Rewind:  January 15, 2024

“Tales from Warren County’s Bootleg Trail”

by Dave Waite

In October of 1919, the passage of the Volstead Act granted the power to enforce the 18th Amendment to the Constitution, what we remember today as Prohibition, which had been enacted 9 months earlier. With the prohibiting of the production, transportation, and distribution of alcoholic beverages across the United States, illegal booze soon began pouring in across the 64-mile land border between Canada and New York State. As border crossings were often left unattended at night, when darkness fell hundreds of bootleggers on foot, horse, and motorized vehicles entered our country and headed south along what became known as the “Bootleg Trail.” With the limited number of suitable roads through northern New York and with many of the destinations due south, these shipments were often carried on roads that in 1927 became Route 9, a main thoroughfare running through small and large communities, including those in Warren County, for its 320 miles from Manhattan to Plattsburgh and on into Canada.

When federal and state enforcement agencies endeavored to stem the tide of this illicit activity, the criminals would either attempt to outrun the law or simply abandon their vehicles and flee on foot. Rarely did they put up violent or deadly resistance when cornered. This changed over the years as criminals realized that waylaying the bootleggers and relieving them of their load was more profitable than carrying them across the border themselves. The country even took up a slang term for these thieves: High Jacker, likely a shortening of “Highway” combined with the word Jack, which carried the meaning of “one who robs.” These criminals, sometimes posing as law enforcement officers, were willing to use violence and had no concern over endangering innocent lives.

To respond to this threat, bootleggers were soon accompanied by armed escorts, with shootouts on the roadways an inevitable result. Even the populated areas along the bootleg trail were not immune to these dangers, with caravans of high-powered cars speeding through communities and gunfights even erupting as far south as the outskirts of Saratoga Springs. As these battles endangered the local population, police began running the routes followed by bootleggers in hopes of ending the ambushes. As we will see, the results would sometimes turn deadly for those on either side of the encounter.

The Death of Trooper Donivan

On the night of October 8, 1923, Trooper Roy Donivan and three other plain-clothed officers were traveling out of Glens Falls on Route 9 into the Saratoga County Town of Wilton in hopes of trapping hijackers, when they were confronted by an armed man whose automobile was blocking the road. With a flashlight shining on the troopers’ car, the high jacker commanded them to “stick um up!” to which Donivan responded by stepping out of the car and firing his gun towards the light. The response was return fire from the back of the bandit’s car, mortally wounded Trooper Donivan.

Of the men who participated in the murder, one was Matthew W. Slavinski, who when arrested did not yet know that Donivan had died, and quickly gave up the names of the other two. One of these, 20-year-old George Haupt, had been shot as they fled and was later left in Watervliet by his partners. Once he was released from the hospital, Haupt was quickly arrested and charged with first-degree murder for the death of Trooper Roy Donivan. The third man, William C. King, had disappeared during their escape south and was never found.

Over the following months, trials for both Haupt and Slavinski were held. Haupt was acquitted on the First-Degree Murder Charge and released back to Elmira on a parole violation. A verdict of guilty of manslaughter was given to Matthew Slavinski, and he was sentenced in Saratoga County Court to six years in prison.

Incidents in Warrensburg & Schroon Lake

Early one morning in the spring of 1924, two automobiles were seen racing along Main Street in the village of Warrensburg, quickly followed by the sound of squealing tires and a resounding crash. A bootlegger attempting to flee from a revenue officer lost control and collided with a telephone pole, tearing the roof off his automobile, and sending bottles of ale and wine smashing to the street. The driver, identified as E. J. Johnson of Schenectady, was taken to Glens Falls Hospital and soon after charged with transporting illegal alcohol. In a newspaper report of the accident published in the May 21, 1924, Glens Falls Times, onlookers were seen holding some of the intact bottles, though they likely were unable to benefit from their find as the police were standing nearby.

With headlines in newspapers across the regions that included “Seeks Thrill Bootlegging,” and “Girl Bootlegger,” in June of 1924 the public was introduced to the short-lived criminal career of eighteen-year-old bootlegger Georgia O’Neil. Heading south near Schroon Lake with O’Neil at the wheel of a liquor-filled truck, state troopers were alerted by a woman’s loud cry of recognition as they passed each other on a backcountry road. Giving chase, the police soon pulled alongside the bootleggers, who responded by locking their brakes and jumping from the moving vehicle. O’Neil quickly fled into the woods, with her partner heading off in the opposite direction. Hampered by the thick underbrush, Georgia was quickly apprehended and brought back to the road badly bruised and clothing torn. When later asked to explain her actions, she shared that it had come from her “Love of Excitement.” With fifty-two cases of Canadian Ale found in the truck, both O’Neil and her partner Charles Howfer were held on $1,000 bail, soon to stand before a Federal Grand Jury.

Bootlegger Roy Brown Loses His Life

For our last look at Warren County bootlegging, we will consider an encounter that has all the makings of an action scene from an early “B” grade movie.  On a winter afternoon in December of 1924, three New York State Troopers were on routine patrol heading north out of the hamlet of Horicon on the Brant Lake-Graphite Road. A short time after they left Horicon, they encountered the first part of a fast-moving caravan of automobiles traveling south. The troopers stopped just north of a tight curve locally known as the “Elbow Turn,” where the men spread out across the road and attempted to stop another pack of four high-powered Packard automobiles as they came into sight. The drivers responded to their demands with increased speed, so the officers fired their weapons at the tires and radiators of the passing vehicles. The last automobile in line, seeing the fusillade that the cars ahead had passed through, obeyed, and pulled off the road.

When approached by the troopers, the two men in the car quickly explained that they were not with the other autos but were only following in their wake. When questioned further, one of the men, Don Judge of Plattsburg, revealed that the leader of the group of bootleggers was his brother Carl. In an action that seemed to defy any logic, the police seemed uninterested in this news and responded by admitting that their Ford automobile was not fast enough to catch the caravan and they continued north on their patrol. The police that day were not aware that bootlegging was a Judge family business, with Don, Carl and their father Frank having been previously convicted of transporting illegal liquor, and another family member, John, a lawyer who was always available to represent them in court. What the police also did not know was that one of their shots had hit home and Roy Brown, the last bootlegger to pass them, was lying near death only a short distance south of where they stood.

When Judge and his companion left the police and came around the curve they were confronted with a wrecked Studebaker and the driver collapsed in an adjacent field. Wounded in the back by a bullet that had deflected as it passed through the car, Brown had somehow kept control around the curve and then leaped from the moving vehicle. As he fled, the car traveled another 250 feet, finally crashing into a guardrail. When they got to the scene, Don Judge and his companion William Hicks quickly carried the mortally injured bootlegger to their car. Judge then drove Brown to Chestertown, leaving his companion behind to deal with the wreck. Not wanting to lose the load, Hicks had the damaged Packard towed to Horicon, repaired, and driven to Chestertown where the bootleg liquor was removed.

Roy Brown either died at the scene, or on the way to help, as when they arrived at Chestertown the doctor immediately pronounced him dead. As questions arose concerning Brown’s death, on January 21, 1925, the Warren County Grand Jury heard testimony and quickly refused to indict the three State Troopers involved in his death. During the investigation by the jury, it was revealed that Brown had fired three times at the officers, and tried to run one of them down before they opened fire at his car. It also came to light that in the coroner’s opinion, Brown might have lived if he had not jumped from his car and ran, which likely increased his heart rate and bleeding.

In the years after Roy Brown’s death, increased patrols and enforcement of Prohibition laws greatly reduced the flow of illegal alcohol into New York. Prohibition ended on December 5, 1933, with the ratification of the Twenty-First Amendment, and with it, the bootleg era of the 1920s.



New York Times, October 9, 1923, Road Bandits kill a State Trooper

Knickerbocker Press, June 5, 1924, Seeking Thrills

Catskill Mountain News, December 26, 1924, Dead Man Victim

Research materials for this article include the book Rum Across the Border, by Allan S. Everest as well as the online newspaper archives at and



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