My Uncle Was a Bootlegger…Jacksonville 1923



So the story goes, my maternal grandmother had a very tragic early life. She was 9 years old when her mother and a brother died in the 1918 Flu epidemic. John Miller Dugard had six children without a mother, and a few years later, another showed up on the doorstep. The oldest son, Clarence, got into the liquor-selling business for local bootlegger, Buford Simmons. He left home so he wouldn’t endanger the family, and took up residence in the somewhat dubious shanty town called Jacksonville, on the upper Cave City Road, or what we now know as Lexington Drive.
Eleven years back, Henry Royse had a morning program on his radio station called the Archives, where he would talk about things that happened on this day 10, 20, 30, and so on, years ago. He read from an article dated in the summer-fall of 1923, that showcased the local law enforcement’s crack-down on notorious bootleggers. It had a picture of a display of liquor confiscated, matching amounts to the bootlegger who had possession of it at the time of arrest. Warren Tobin’s name was attached to a case of fifth whiskey bottles. Another’s name was attached to a moonshine jug. Clarence Dugard’s name was attached to a half-pint bottle.
Henry was puzzled at this one small bottle attached to such a notorious man, who was known to have outrun the Hart County Sheriff’s officers in a high speed chase. I laughed and told Henry it was a joke on Clarence, because he stood about 5 feet tall in his socks, and weighed about 100 pounds soaking wet. The reason his working for Buford Simmons turned out so well as long as it did was that Clarence could get behind the wheel of Buford’s car, escort Buford’s pretty wife around town, and Clarence looked like a young boy, as he could barely see over the steering wheel. They kept the liquor concealed behind false panels in the car doors. And you should be able to guess that the liquor came in half-pint bottles!
Keep in mind that this was the Prohibition era, and Barren County has always been dry, meaning that it has never allowed the sale of alcohol until only a few years back, when Glasgow was voted “moist”, to allow alcohol by-the-glass, in restaurants that seat more than 100 people.
What I know of events of 8 December 1923, I have obtained from newspaper articles, Clarence’s death certificate, and eyewitness accounts of family members and associates. It was a messy situation, and I’m sure that Clarence, as well as the others involved, knew this. My grandmother told me that what little she knew of the situation was that Clarence was at Buford’s house, trying on his wedding clothes. At the time of this writing, I still have been unable to find out the name of the girl he was to marry. But several people have corroborated this.
My mother’s aunt, Katherine Abston Gass, told me quite a bit more. Katherine’s mother, Janie, was Buford Simmons’ sister, and she was called out there after the incident. Katherine was a small child at the time and she distinctly remembered the whole incident. Janie told her when she got older that “the boys” had been arguing and fighting amongst themselves, and one of them had a very personal problem with Clarence. They all assumed the young man who actually killed Clarence, was sweet on the girl Clarence was to marry.
Buford Simmons was fed up with their shenanigans, and decided to leave for town – Glasgow – and he left Buford Wood in charge, telling him to let them “fight it out.” Clarence had been Buford’s right hand for some time, and he had a reputation for being a dirty fighter. He usually carried a concealed derringer, and also a stiletto knife in his right boot, which he could draw and throw faster than a man could draw a pistol. He also packed a nasty pair of what were called “horse pistols.”
But things went south fast while Simmons was gone, and Wood had stepped outside for some fresh air. Clarence had gotten his clothes on and was sitting down in a chair, reaching for his boots to put them on, all the time talking with the young man who was so very angry at him, for exactly what reason we will never know. When the young man saw Clarence reach for his boots, the boy’s nervousness got the best of him, and he drew a gun and fired on Clarence, shooting him twice before anyone there could wrestle him to the floor and disarm him.
The damage was done – Clarence died a short time later from a gut shot and a chest wound. Buford Wood was horrified by the situation, and told someone else to take care of the guilty young man, who shall remain unnamed here. Needless to say, he was also under Buford Simmons’ protection, and his patience had worn thin over the young man’s problems with Clarence, as Clarence was a favorite. When Simmons returned, and was told what had happened, he got back in his car and went to the Sheriff’s office. The following is an abbreviated account of an article from the Glasgow Times, dated Thursday 13 December 1923.

Clarence Dugard shot through the body 3 times at the home of Buford Simmons.
“I shot Clarence Dugard,” declared Buford Simmons as he stepped into Sheriff Shaw’s office Saturday evening at dusk.
“How badly is he shot, Buford?” asked the Sheriff. “Sorry, but I killed him,” was the reply.
Investigation led to the finding of Dugard’s lifeless body at Simmons’ home at Jacksonville, the bootleg colony of Glasgow. He had been shot 3 times – once through the stomach, once in the chest, and the third a slight flesh wound. Dugard’s pistol, said to have 3 blank shells in it, was found by his side.
Simmons and Dugard were friends and associates, Dugard having been a liquor-runner for Simmons. Both were bootleggers and went armed, and the killing was a natural result of their calling. Simmons gave no reason for the killing except to remark to jailer Mansfield that he shot in self-defense. Simmons is out under $1000 bond for his appearance in an examining trial here next Tuesday. Mr. BG Ellis signed his bond.
Dugard, like Simmons, has often been in trouble. His last offense was an escape from Hart County officers when they arrested Warren Tobin on a charge of having liquor in his possession. He was later freed of all charges in this case and turned loose to further prey on society.

* * * * * * * *

One of the 3 wounds listed as Clarence’s was actually Buford Simmons’ – the flesh wound. I was never able to determine from other sources how Simmons received the flesh wound, but he claimed self-defense to the jailer. I was able to find out the pistols belonging to Clarence had disappeared earlier in the day and led to Clarence’s argument with the young man who killed him. The young man thought Clarence was going for his knife, and his jumpiness had went to full-blown panic. When confronted by Buford Wood, and later Simmons, the young man claimed self-defense, although everyone knew he was angry at Clarence already, and they were pretty sure he had taken Clarence’s pistols earlier that day.
This particular young man had had mental problems most of his life, and it wasn’t long after Clarence had died and Buford Simmons went off to the penitentiary for a murder this young man committed in order to protect his fragile state of mind, that the young man was committed to Western State Hospital in Hopkinsville. He died there in 1945 at the age of 41.
Buford Simmons spent several years in the penitentiary, but he had been out for some time when he died in 1955. His son, Bill Simmons, ran Simmons Drug Store on the Square for many years.
Clarence is buried in New Salem Cemetery in an unmarked grave, near his parents, a brother, and a sister. He was 22 years old when he died.
On a final note on Jacksonville, another excerpt from the Glasgow Times, dated Thursday 20 December 1923.

Bootlegger Row stretches along Cave City Road just outside Glasgow City Limits (AN: This is actually Lexington Drive, or Old Munfordville Road).
A bootlegging colony exists at Jacksonville, where Simmons makes his home; members of that colony were Dugard, for whose murder Simmons was being tried, Simmons himself, the Tobins, Bledsoes, Ballards, and a host of others of lesser light.

* * * * * * * * *

Please note that these were the words of the journalist of the time and not mine.
And lastly, the house that Clarence Dugard was shot and killed in is still standing, on Lexington Drive, shortly before you get to the Pebble Drive subdivision. It has been used as an outbuilding as far back as I can remember, but still stands as a reminder of a bygone era of booze, gambling, and other nefarious deeds that law enforcement spent many years and man hours trying to suppress.
Now, it’s just another Urban Legend… that my uncle was a bootlegger!
On the following map, Buford’s old house is in the middle with a barn with a metal roof close to it.,-85.916235&spn=0.002476,0.003449&hnear=Lexington+Dr,+Glasgow,+Kentucky+42141&gl=us&t=h&z=18


About Gclee

I am a long time genealogy and local history hunter from Barren Co., KY. I have many stories to share that may be of interest to other local genealogists and history buffs. I enjoy this as a hobby and hope I can be of encouragement to others. I also hope everyone enjoys my stories as much as I have enjoyed learning about them.
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2 Responses to My Uncle Was a Bootlegger…Jacksonville 1923

  1. Debbie Perkins says:

    I would like to talk to you about your research. My grandfather, Willie Bunch, had at least 2 experiences with a headless woman on the Kino Road.

  2. Gclee says:

    Don’t know how much more I can add at this time. I still haven’t found out who she may have been, but most of the families that lived out there – Bunch, Dugard, Groce, Bailey, etc. – have claimed to have seen her at some point while they lived out there.

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