Moonshiner Jack: A Modern Jack Tale

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Moonshiner Jack
Jack and his brothers hid their moonshine still in a cave.

As I wrote a blog post about Jack Tales, I was motivated to try my hand at writing a Jack Tale of my own. Drawing from literary descriptions of Jack, local moonshiner stories, and a neighbor’s tale of a mash-consuming, drunken bear, I put together a short tale about Jack, a drunken bear, and a sheriff.

Most of us are familiar with the tale Jack and the Beanstalk, about an English boy who bested a giant. What’s less well-known is that English Jack had an American cousin (also named Jack) who lived in Carroll County, VA. Our story takes place in 1931 when the Great Depression and Prohibition were in full swing. But those calamities had little effect on Jack. You see, Appalachian Jack was a moonshiner, and business was booming.

The Whiskey Business

The moonshine operation was well organized. Jack’s two brothers, Tom and Will, distilled liquor in a well-hidden, well-ventilated cave. Jack drove and made deliveries.

One day, three Chicago mobsters came to town and placed a huge order for moonshine whiskey. The brothers were thrilled with the large order but worried about fulfilling it. Sheriff Berrigan was coming down hard on moonshiners. Many of Jack’s colleagues had been shut down, jailed, and their stills destroyed.

Jack Tale drunken bear
The drunken bear created havoc in the town

Plus, the brothers had a new problem: A big black bear had discovered where they stored their used corn mash and had become very fond of the sweet (but alcoholic) mash. The often-drunk bear had already caused trouble, prowling the woods and venturing into town, creating chaos and fear.

Jack and his brothers had to find a way to produce sufficient whiskey, evade arrest, and deliver their goods to Chicago. If they didn’t, they faced jail time, retribution from the mob, or both.

So, they devised a plan: they would run the still 24/7, adding more sugar to the mash to boost the alcohol content, and then cut it with creek water to adjust the alcohol level and quantity. The hooch would be bottled in stoneware demijohns labeled “maple syrup.” Jack would carry the demijohns down the mountain by mule and store them in several barns, where he would pack the hooch into shipping crates and deliver them to the N&W train station in Galax for transport to Chicago.

The Sheriff

Unfortunately, the Bureau of Investigation had been watching the mobsters. They tipped off Sheriff Berrigan that some heavy hitters from Chicago were coming his way. Berrigan knew they would be buying from Jack, which meant trouble. Jack was a slippery fella: he drove a souped-up Model A Ford that could outrun any car the Sheriff had. Jack knew the dirt roads through the hills and hollers better than anyone in the county. Catching him would be tough.

Jack’s Clever Plan

Seeing an opportunity to outwit the Sheriff, Jack set a trap. He gathered a large amount of corn mash and spread it from the storage spot to a barn where Jack placed barrels full of mash. He fortified the mash with whiskey to ensure the bear would be extra crazy. Then, Jack hid and waited for the lawmen to arrive.

Jack Tale Sheriff
The sheriff and his deputies ran from the drunken bear.

The Bear Encounter

The bear, attracted by the smell, followed the trail of corn mash to the barn and began knocking over barrels and devouring the mash. Meanwhile Sheriff Berrigan and his deputies, thinking Jack was cornered, aggressively charged into the barn. What they found was a drunk and aggressive bear. Chaos ensued. Deputies scattered, screaming, and climbing into the loft. Jack seized the moment, closed the barn door, and locked it.

Jack’s Triumph

With the Sheriff thoroughly distracted, Jack hopped into his loaded Ford and headed to Galax. He reached the train station without a hitch. The crates of whiskey were loaded, and the contract with the mobsters was fulfilled. Jack couldn’t help but let out a satisfied chuckle as he imagined the Sheriff’s bewildered face when he realized he’d been outsmarted again.


Embarrassed by the bear incident, Sheriff Berrigan became the subject of local jokes, earning the nickname “Sheriff Bear-Bait.” Jack and his brothers continued their moonshining operation, outsmarting the Sheriff at every turn and maintaining their reputation for producing the finest moonshine in Carroll County.



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