The “OLE” Kentucky Bar-Daytona Beach, Florida

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Ray Hahn

The “OLE” Kentucky Bar

Daytona Beach, Florida

On Sunday morning, March 10, 1918, the Hopkinsville Kentuckian [published by Charles Meacham in Christian County, Kentucky, from 1889 to 1918.] reported news from the area draft board. The board announced, as they did in those days, lists of names of young “registrants” who were expected to report for duty. And, as was the practice at the time, the names appeared in the newspaper in two separate lists – the first was of approximately 40 “white” men, the second was a list of over 120 “colored” men.  That Sunday, one young resident of “the city” named Raymond Ennis Wiley found his name near the end of the “white” list.

Raymond – who later used only his middle name – was the son of a Hopkinsville carpenter named Elbert Wiley. Elbert was apparently a successful businessman and enjoyed a congenial family life with his wife Lucy and their daughter Mary and three sons Howell, Ennis, and Gus.

No account has been found that reports the results of that March 1918 “call to duty” but it can be assumed that the quota of 150 men was met. Nevertheless other military records, from that era, make it clear that Ennis Wiley served in the U. S. Navy and for a brief time he served aboard the USS Kansas, from mid-1918 to early 1919. Navy personnel records add that while in the navy Ennis was, for unknown reasons, a patient in Breast, France, Naval Base Hospital #5 until April 1919.

Mr. Wiley was discharged from the hospital and returned to his home and married Grace Morse on May 8, 1919.

Federal census records track Mr. and Mrs. Wiley through the next three decades. In 1920 they lived in Hopkinsville. He drove a taxi and she was a sales lady in a dry-goods store. Sometime in the next few years they moved to Texas and in 1930 he was working as a plasterer, and it seems that by the end of that decade their lives changed again, and this time quite significantly – they moved to Daytona Beach, Florida.

It was in Daytona Beach that Ennis and a fellow named Silas Cunningham bought a restaurant named the Centurian. Ennis and Silas renamed the restaurant the Ole Kentucky Bar and Silas managed it for at least one year, but then Silas completely disappeared from public records.

The postcard below comes to Postcard History to have its history told from March 1939.   

Most postcard dealers will concede that cards like this are the ones that remain unsold for years unless a collector comes along with a keen interest in interior views of spaces for social or entertainment events. This card was found in a “to be filed” box in a paper ephemera dealer in a Virginia antique shop. It was mailed in March 1939 from Daytona Beach, Florida, to Mr. & Mrs. Peterson of Park Avenue in Richmond, Virginia.

The message reads: This is the life! We are thriving and this is where we seem to spend most of our time!

The caption reads: “Meet me at the OLE Kentucky Bar at the corner of Main and Coats Streets, Daytona Beach, Florida. Free dancing every evening. Beer, sandwiches, wine, and liquors. Telephone 9109. Wiley and Cunningham, proprietors.

As the card was examined the names Wiley and Cunningham “called” to me. My first thought was of the poem High Flight by John Gillespie Magee, “Oh! [they] have slipped the surly bonds of Earth, And danced the skies on laughter-silvered wings; that is if they were adults at the end of the 1930s. So, I pulled on my genealogist’s cap and went to work.

Mr. Raymond E. Wiley died at age 71 on February 1, 1960; his wife Grace outlived him by more than a dozen years, she died at age 76 on June 5, 1973. They rest side-by-side in Riverside Cemetery in Hopkinsville, Kentucky.

The research process started with a call to the historical society in Daytona Beach. I talked to Jamie and shared what I knew about the card and the research that I had completed. He was interested immediately, for he had no knowledge of the Ole Kentucky. However, like any good researcher with a long run of R. L. Polk City Directories he was able to identify Silas Cunningham. Jamie also found among his regular patrons someone who remembered the name of the establishment after Wiley and Cunningham were out of the picture. That would have been sometime prior to the 1950 census. The new owner renamed the place Uncle Tom’s Tavern, and it remained so until at least 1965.

[Postcard History thanks the historical society in Daytona Beach and salutes Jamie for his help in preparing this article.]

And, what is it today?

The building is still in use as a restaurant and grille and as it was in 1939 there is a good chance it is still a place that people will talk about and say, This is the life! We are thriving and this is where we seem to spend most of our time!

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The card looks like the photo of the bar that my grandfather’s family had in New York City. His job as a kid was to deliver pails of beer to local workers. It was the “take out” of the time, delivered by a kid. I wonder if this bar provided that service.

I noticed an advertising sign for Pabst Blue Ribbon beer above the bar. I’m guessing that that brew was on tap at the OLE Kentucky Bar.

In addition to Travel and Transportation themed cards, these type of scenes inside old time businesses are some of my favorite. To me they really help to capture a sense of the times back then. I have several RP cards of people inside their butcher shops, barbershops, drugstores etc. Nice backstory on this card as well. Thankyou for sharing this.

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