A town divided: Tennessee-Kentucky matchup creates interesting divide for border town

Middlesboro, Ky. shows how being on the border between Tennessee and Kentucky mixes allegiances.
Published: Oct. 16, 2020 at 6:00 PM EDT
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MIDDLESBORO, Ky. (WVLT) - Middlesboro, Kentucky rests on the border between the Bluegrass State and the Volunteer State.

Nearly two hours from Lexington, and an hour and a half from Knoxville, in this town there are fans of both Tennessee and Kentucky.

In the corner front window display of Henry’s Flower Shop, you can see the inner struggle of a city divided.

“We have a great time in the district here. You can see people in their orange and some in their blue, and different little things, we’ll have different little contests and different bets, we have a good time with it, it’s wonderful,” said Waylon Allen, Superintendent of Middlesboro Schools.

Allen has both sides of the aisle on his staff, and three times a year, things get interesting.

“If we win, which happens to not be much, but I will say the last two times we won I happened to be at the game, I make sure to rub it in and I’m not as nice as they are,” said Sheila Smith an instructional coordinator for Middlesboro Schools.

Smith and Allen have to work side by side with Vol fans like Jon Shipley and Zach Massengill.

“As long as I can remember {I’ve} been a Tennessee fan, mom and dad are Tennessee fans, some more family members are Tennessee fans, it’s just kind of born and bred into us,” said Shipley.

In this town of nearly 10,000, even little league football games get moved for Kentucky vs. Tennessee.

“We take it seriously around here. I know there were some middle school games that we actually moved because it conflicted with the kick-off,” said Massengill.

In this family, there are side bets, games, and everything you can think of to keep things interesting, but for roughly four hours, a couple of Saturdays a year, it’s no laughing matter.

“The texts will start rolling in tonight and they’ll go through the game tomorrow and then somebody’s feelings will get hurt tomorrow afternoon, but hopefully it’s the Kentucky fans,” said Massengill.

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