MIDWAY, Ky. — He thought he would be the mayor of Midway for the next two and a half years, but a Kentucky law may upend his tenure.

“There’s a strange little quirk in Kentucky’s law where, if a vacancy happens a certain amount of time from an election, it actually triggers a special election in that next November’s ballot. Well, we didn’t know about that,” explained Grayson Vandegrift, who currently serves as mayor of Midway.

He was appointed mayor by the city council back in May, with the plan being to fill the term of his vacating predecessor.

“So, when the council appointed me to fill an unexpired term back in May, I like … they thought that they were appointing me for two years and seven months, the remainder of that term,” he said.

Now, Vandegrift faces an unforeseen dilemma. He wants to keep his job, but because he missed the filing deadline to be a candidate, his name won’t be on the ballot in November.

“Typically, you’re going to have your name on a ballot and you go up to the ballot and you vote and you vote for who you want. But in this sense, the votes will only count for who will serve as mayor the next two years, starting Jan. 1, 2025 through Dec. 31, 2026. They’ll only count if you write the name of your candidate in, and it’ll only count if that candidate filed to be a write-in candidate,” he explained.

So where one opportunity ends, another begins. The mayor’s only option is to be elected to his current position by mounting a write-in campaign.

“So, in reality, it’s actually an opportunity to now go and have the people directly elect me for the next two years. I don’t know that I’ve ever written in a candidate,” he explained.

A challenge that Vandegrift hopes will rest with a pen in the hands of voters this coming November.