Caldwell enters city race focused on service

In his 25 years as a mete­o­rol­o­gist, Jim Caldwell helped peo­ple in small towns weath­er storms and look for­ward to brighter days. Now he wants to do the same as a Winchester city commissioner.

Caldwell, who is orig­i­nal­ly from Eastern Kentucky and began his radio broad­cast­ing career in his teens, is best known as a for­mer mete­o­rol­o­gist at WKYT in Lexington. He is now the pub­lic rela­tions and mar­ket­ing direc­tor for the Kentucky Educational Development Corporation (KEDC), where he works along­side school dis­tricts across the state to sup­port stu­dents, edu­ca­tors, and communities. 

He makes his home in Winchester with his wife, Terri, who works in nurs­ing, and their teenage son, Storm.

“Winchester isn’t just where I end­ed up, it’s where I chose to be,” Caldwell said. “I saw some­thing spe­cial in this com­mu­ni­ty, and I want­ed to be a part of it.”

He wants to give back to his home­town by serv­ing in its government.

“While this is my first run for pub­lic office, serv­ing the pub­lic has always been at the heart of what I do,” Caldwell said.

He said that in his years in tele­vi­sion, he had a “front row seat” to observe what hap­pens when things go right and when they go wrong.

“I’ve seen cities across Kentucky deal with growth chal­lenges, com­mu­ni­ca­tion break­downs, and moments of real chaos. Sitting behind the desk, you find your­self think­ing, ‘There’s a bet­ter way to han­dle that.’ You’re coach­ing from afar, but you’re not in a posi­tion to actu­al­ly fix it. Now I am,” he said.

Caldwell said he is run­ning for city com­mis­sion­er because he cares deeply about Winchester and its future.

“I chose to build my life here because of the peo­ple and the sense of com­mu­ni­ty, and I want to help pro­tect and grow that,” he said. “I don’t see this as pol­i­tics, I see it as service.”

“What I bring to the table is real-world expe­ri­ence in com­mu­ni­ca­tion, prob­lem-solv­ing, and work­ing with a wide range of stake­hold­ers,” Caldwell said. “I’ve had to take com­plex infor­ma­tion and make it clear, calm, and action­able, often in high-pres­sure sit­u­a­tions. That mat­ters in leadership.”

“I also bring a fresh, inde­pen­dent per­spec­tive. I’m not tied to the old ways of think­ing, and I’m will­ing to ask ques­tions, lis­ten, and focus on what’s best for the peo­ple of Winchester,” he remarked.

Caldwell said he sees the biggest issues fac­ing Winchester as smart, respon­si­ble growth, eco­nom­ic devel­op­ment, and qual­i­ty of life.

“Winchester is grow­ing, and that’s a good thing, but it has to be done the right way,” he said.

The city needs to ensure its infra­struc­ture — includ­ing roads, util­i­ties, and pub­lic ser­vices — keeps pace with its growth.

“That means thought­ful plan­ning, work­ing close­ly with devel­op­ers, and mak­ing sure we pro­tect what makes Winchester spe­cial while still wel­com­ing new oppor­tu­ni­ties,” he said.

Caldwell said Winchester needs to con­tin­ue attract­ing busi­ness­es and jobs while also being a place where peo­ple want to live, not just work. That includes sup­port­ing local busi­ness­es, improv­ing recre­ation­al oppor­tu­ni­ties, and mak­ing sure the com­mu­ni­ty remains safe, vibrant, and fam­i­ly-friend­ly, he added.

“Strong schools, strong work­force con­nec­tions, and com­mu­ni­ty part­ner­ships all play a role in that,” he said. “That’s some­thing I see every day in my work with KEDC, and I want to bring that same mind­set here locally.”