Monday, February 19, 2024

Prohibition’s most audacious con

old newspaper headline

By Dave Waite

In October of 1919, Congress passed the Volstead Act, legislation enforcing the ban on alcohol in the United States. With Prohibition enacted, enforcement became a part of the daily work of state and federal police across the country. In New York, the sixty-four-mile land border with Canada offered nearly unlimited opportunity for those on foot, horseback, and motorized vehicles to transport illegal alcohol for delivery to major cities through New York and the East Coast. Called Bootleggers, a term first used during the Civil War for soldiers sneaking liquor in their boots, these men, and occasionally women, risked fines, jail, and even death to carry their cargo south.

When federal and state enforcement agencies endeavored to stem the tide of this illicit activity, the criminals would 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.

In what seemed at the time simply another effort by the government to fight the flow of illegal alcohol, in the summer of 1921 two members of the United States Federal Constabulary showed up in Upstate New York. Traveling on a motorcycle with a sidecar, Third Lieutenant Henry K. Fielding, commander of Troop 75, accompanied by Trooper William L. McArthur, approached the Sixty-Fourth infantry as the detachment of foot soldiers, cavalry, mule-drawn wagons, and accompanied by a band, moved from Camp Meade, Maryland, to their new post in Plattsburgh.

When they were taken to the commanding officer, Major R. John West, Fielding announced that they had been sent to act as guides and regulate traffic for the regiment. With well-tailored gray uniforms, regulation sidearms in belts bearing the initials “U. S. C.” and official-looking photo identification cards, Major West sent them to the head of the column to lead the way. Arriving in Plattsburgh, the two officers were treated as honored guests and entertained at the base Officer’s Club. What the Army did not know is that Fielding and McArthur were con men who had concocted a scheme to infiltrate the ranks of law enforcement and use the illusion of authority to obtain illegal liquor as it came across the border of Canada.

The name Conmen is a shortening of the name coined in the 1840’s “Confidence Men.” These bold con men even fooled a United States customs agent who encountered the two soon after they had waylaid a bootlegger. After showing identification and telling the agent that they had been “instructed to assist in putting down rum running,” they even offered to turn over the prisoner, but were assured that as it was their arrest they could continue. These were impostors who took on an air of authority to gain an advantage over others. In this case, taking on the role of federal representatives to steal from bootleggers.

old newspaper headline about bootleggers

For nearly a year the two fake federal officers patrolled the north country stopping bootleggers as they crossed into the United States. Once detained, the criminals were taken before another con who posed as a local justice of the peace and relieved the bootleggers of their money and illegal liquor. In what was a well-thought-out method of perpetuating their work, the bootleggers were then admonished to no longer bring booze across the border and released to leave in their own vehicle.

As bootlegger after bootlegger was successfully robbed, the two conmen expanded their operation into the Mohawk and Hudson Valley and deputized local residents into their federal force. One of these volunteers was Saratoga Springs bar owner Michael J. Sweeney. He had become acquainted with the two con men in the fall of 1921 when they had escorted the Sixty-Fourth through Saratoga Springs on their march north. He later met up with the two in Plattsburgh and was brought into the force a few weeks later.

Their elaborate scheme began to unravel on March 14, 1922, when the two conmen, accompanied by Sweeney, waylaid a bootlegger near Schroon Lake. During the stop, a United States customs agent out on patrol made an appearance. Showing their identification, they were allowed to continue with the arrest. Not knowing what to make of his encounter with these constabulary officers, the agent began investigating and soon realized that they were impostors. Continuing to pursue his inquiry he located the driver of the car that had been stopped that night and convinced the man to press charges as he had been robbed of one hundred dollars. The three were arrested on March 28th while driving their touring car with federal license plates from Plattsburgh to Saratoga.

old newspaper headline

With the presumption of innocence in play, Fielding was released on one thousand dollars bail and McArthur paroled into the care of a Plattsburgh Army officer. At this time Sweeney was also released on bail. When the hearing date came all three were no-shows before the United States Commissioner in Plattsburgh. While Sweeney had requested an adjournment by mail, Fielding and McArthur had fled to parts unknown. Unable to question the two conmen, the case was dropped without any further action towards Sweeney.

While Michael Sweeney may well have been just one of many who fell for this con, it is also possible that he saw through the ruse and participated for his own advantage. Less than six months before the three were arrested he had been fined five hundred dollars for keeping a gambling room. During the trial, it was revealed that earlier he had pleaded guilty to smuggling liquor and paid a fine of one hundred dollars, with his attorney saying that proof of his innocence was that he had stopped bootlegging months before. Finally, only three months after the hearing in Plattsburgh he was charged with possessing intoxicating liquors when his bar, the Adirondack Inn, was raided and five quarts of whiskey and other bottles of prohibited alcohol were found.


Two Thieves Form Federal Constabulary, Syracuse Journal April 20, 1922

Court Move Bares Prize Fraud Stunt, Knickerbocker Press April 20, 1922

Say Sweeney Had “Commission,” Saratogian April 8, 1922

Sources for this article include the newspaper archives at and

Dave Waite has had a lifelong interest in the Adirondacks and often spends time exploring the park and learning about its history. His stories about Adirondack and Upstate history have been published by several historical societies including those in St. Lawrence, Warren, and Saratoga counties. Dave recently published his first book, Thrilling Attractions and Weird Wonders, which brings together over 30 of his stories from Saratoga County and Upstate New York. 

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The Adirondack Almanack publishes occasional guest essays from Adirondack residents, visitors, and those with an interest in the Adirondack Park. Submissions should be directed to Almanack editor Melissa Hart at

3 Responses

  1. Wayne Miller says:

    Great piece!
    For more on prohibition in the North Country, the best (only?) book is
    Rum across the border : the Prohibition era in northern New York
    Format: Books
    Author: Everest, Allan Seymour.

  2. Joel Rosenbnaum says:

    Reminds me of the old folksong we used to sing in Northern New York (Chateaugay):
    To the tune of “The Wabash Cannonball”:

    It was on a Monday morning when we traveled to the North,
    On a road we often traveled when going back and forth,
    Across the wide St Lawrence and up to Montreal,
    We’d loaded up our Packard with beer and alcohol,
    Loaded up with whisky, and topped it off with ale,
    We had to pass the customs and knew we couldn’t fail,
    They signaled us with flashlights and a rifle call,
    But we drove right through those customs with our load of alcohol.
    Got to Moira, Brushton and Malone,
    The only way to cut us off was by the telephone,
    Got to Turner’s Crossing, with a train across our road,
    So boys, we left our Packard,
    our Packard and our load.
    They took us to the courthouse and threw us into jail,
    We had a lot of friends in town but none would go our bail.
    Now we’re out on bail, I guess we lost it all,
    Waiting for our trial, scheduled next Fall.
    So come all you young sinners and never take the chance,
    To carry that precious water that makes you sing and dance!

    • Joel Rosenbnaum says:

      Sorry. I left a couple of lines out:

      They signaled us with flashlights and a rifle call,
      But we drove right through those customs with our load of alcohol.

      The border policemen soon took up the chase,
      But we were doing 95 and steady held our pace,

      Got to Moira, Brushton and Malone,
      The only way to cut us off was by the telephone,

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