James Bowman, a military veteran and young entrepreneur, says he’s running for city commissioner because he’s invested in his community and knows what it needs to thrive.
He not only wants to attract new businesses, but keep those that are here, work with developers to provide incentives for affordable housing, and help make his city a place that offers opportunities for work and leisure.
“I’m running because I got tired of hearing that ‘there’s nothing to do in Winchester’ and seeing nothing change. So I did something about it,” the 31-year-old owner of High Speed Collectibles said in a candidate survey.
“I took the risk, invested my own money, and built a business that brings people into this city instead of sending them somewhere else,” he said.
“That’s the difference I bring. I’m not a career politician. I’m someone who has actually built something here. I know what it takes to start from nothing, survive the early stages, and create something that lasts. I’ve seen businesses fail here, and I’ve proven what it takes to succeed.”
Bowman said his military and project management background taught him how to lead under pressure, manage large budgets, and deliver results when it matters.
“I’ve worked on projects worth hundreds of millions of dollars where there’s no room for excuses. Winchester doesn’t need more ideas. It needs execution,” he concluded.
Bowman is a lifelong Winchester resident. He graduated from George Rogers Clark High School in 2012 and has been married to his high school sweetheart, Bree, for 13 years. They have two kids, Jayden, 12, and Rylan, 8.
He earned an associate degree in business from Columbia Southern University and served in the military for more than a decade.
For five years, Bowman was on active duty in the Marine Corps as a facilities manager and substance abuse control officer, and for six years, he served in the Air Force Reserve as a structural mechanic on KC-46 aircraft. During that time, he also worked in project management roles supporting federal operations.
“Professionally, I’ve worked in construction and project management on projects exceeding $300 million, managing teams, budgets, and deadlines where failure wasn’t an option,” he said.
For the past five years, Bowman has owned and operated High Speed Collectibles, a game card and collectibles shop in downtown Winchester, which has become a destination for people from across Kentucky and other states. Earlier this year, he and his wife also opened the Book Nook on Main, a bookstore that specializes in fantasy romances.
Bowman says he stays involved in the community by mentoring students, supporting teachers and schools, donating to and supporting local food and toy drives, working with local organizations, and helping families in need.
His top priorities for city government include building a lasting local economy and promoting growth, especially affordable housing development.
“We don’t just struggle to attract businesses, we struggle to keep them,” he said. “Too many open and close within six months. That’s not random. That’s a system problem.”
Right now, he said, the city offers short-term financial help, which is useful, but “doesn’t fix why businesses fail.”
“Most people aren’t prepared for what it actually takes to survive here,” he said. “We need to focus on preparation, not just support. That means helping business owners understand the local market, set realistic expectations, and learn from people who have already made it work.”
“Strong businesses need a strong downtown; empty storefronts don’t,” he added.
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Bowman said Winchester has an opportunity to grow, but it’s not set up to take advantage of that opportunity.
“I’ve spoken with developers who want to build here, especially affordable housing, but many walk away because the process isn’t worth the risk. That’s a missed opportunity,” he observed. “We need to be proactive, not reactive. Work with developers. Create incentives that make sense. Make Winchester a place where growth is possible.”
At the same time, he said, growth only works if people feel safe. Cutting law enforcement positions sends the wrong message. First responders are essential, and supporting them has to be a priority, he insisted.
“If we want people to live here, invest here, and stay here, we have to give them a reason to,” he said.

