FNN Politics and Power: Getting to Know Winter Park Mayor Steve Leary

WINTER PARK, Fla. (FNN NEWS) – Nestled in a treelined historic area just west of Downtown Orlando is the beautiful City of Winter Park. There you will find Winter Park Mayor Steve Leary, who was elected in 2015. But if you’re like me, you want to get to know about the person behind the title. Let’s get to know Mayor Leary–his rise, his family, his career, and why public office?

Mayor Leary, one of 6 children, grew up in Rye, New York and describes his upbringing as “blue collar.” His maternal great grandfather and girlfriend, who eventually married, immigrated from Italy as teenagers with little to no money, family or really much more than the shirts on their backs. In addition to his father working a variety of jobs and his mom becoming a nurse, he learned early on the value of a dollar and the importance of a strong work ethic.

At age 13, Leary began working after school and during summers to help plan and pay for his education. Fortunately, he received a partial scholarship to attend a private school for the final three years of high school. which helped advance Leary to later attend Washington College in Chestertown, Maryland. After graduating Leary moved back to New York, working in the advertising industry with such brands as Miller Brewing Company, United Parcel Service and Merrill Lynch.

Leary quickly excelled in advertising, working with arguably one of the most successful advertising agencies in the world, J. Walter Thompson, focusing on the emerging digital age. Leary eventually became bicoastal, landing a job in San Francisco as he continued to build his career and his resume.

Leary, 52, currently co-owns property management company Leary Management Group with is brother Bill, with twenty-five employees based in West Orange County. The two also co-own and run Flange Skillets International. They manufacture and sell gasket positioning devices primarily to the sub-sea segment of the pipeline industry. Mayor Leary has two patents and commercial divers use their products to seat gaskets in oil pipelines on the ocean floor and in other compromised environments–a far stretch from the world of advertising, but clearly an interesting industry at a time when our oceans and the environment are passionate issues for all Americans.

Mayor Leary ventured into politics and was elected to the Winter Park City Commission (Seat 1) in 2011 and reelected with no opposition in 2014, a clear testament to his community-minded approach to serving the people of Winter Park. In a highly contentious race in 2015, Leary was elected Mayor and reelected in 2018 with 72% of the vote. That too was a pretty impressive win.

So why politics? “I decided to run for office in Winter Park after attending a few City Commission meetings. I realized that younger families were not being represented at City Hall,” said Mayor Leary. “I decided to run to better represent my peers and bring more of a balance to the City Commission. Over the course of my tenure on the commission, we’ve made sure to respect our history, manage our present and plan our future.”

In recent years, that ambition caused Winter Park to pervade the news as the city’s struggle to grow clashed with its desire to maintain its charm as a majestic family destination.

“We’ve increased the number of historic homes, removed billboards, improved our corridors, implemented our first Urban Forestry Plan to proactively manage our tree canopy, increased our electric underground program to harden our utilities against weather incidents, removed the most dense zoning from our comprehensive plan, added parkland, invested heavily in our civic assets by improving our community center, golf course, football stadium, neighborhoods, library and civic center, and many more,” explained Mayor Leary.

Many might think these improvements would come at a high cost to Winter Park residents, but Mayor Leary added, “We did all of this without raising our millage rate in 11 years while at the same time we’ve increased our general fund reserve to almost 30% of our annual budget.”

Former Orange County Mayor candidate, entrepreneur and longtime Winter Park resident Rob Panepinto has great respect for Mayor Leary. “I had the opportunity to get to know Steve pretty well over the last few years. I’ve always appreciated how accessible he was in the community.” Residents and community leaders often comment on the Winter Park Mayor’s accessibility. Panepinto continued, “Even though the Winter Park mayor position may be technically a part-time job, Mayor Leary is always available and always listening to different people’s thoughts and opinions. And trust me, in Winter Park, there are always opinions….as people are very passionate about the community.

“I appreciate that while he definitely has real convictions and ideas, his approach is always balanced, listening to multiple sides of an issue. And of course, I don’t think I’ve ever had a conversation with Steve where at some point, we [don’t] start to talk about wives and families.”

Photo courtesy of former Orange County mayoral candidate and Winter Park businessman Rob Panepinto (pictured).

Photo courtesy of former Orange County mayoral candidate and Winter Park businessman Rob Panepinto (pictured).

“Mayor Leary has been a strong advocate for home rule and for local elected government’s right to self governance. [He] serves on the Florida League of Mayors Board of Directors and he succeeded me as Chairman of the Orange County Council of Mayors,” said former Windermere Mayor Gary Bruhn. “We had the pleasure of working on many local government issues and he was always a pleasure to work with in his commitment and dedication. I consider him a friend.”

Former Windermere Mayor Gary Bruhn. Former Windermere Mayor Gary Bruhn. Photo courtesy of the Town of Windermere.

Former Windermere Mayor Gary Bruhn. Photo courtesy of the Town of Windermere.

Mayor Leary met his wife Caroline in 2001, at which point Leary’s brother was living in Winter Park, which just happened to be her hometown. After Leary’s brother offered him a position to help run his property management company, Leary and his wife moved to Winter Park in 2004. In 2005 they were blessed with triplets: Alexandra, Jack and William.

“My family is the most important thing in my life. Helping make our community a better place to live, work and thrive are at the core of who I am as a husband, father and community leader,” Mayor Leary expressed.

Mayor Steve Leary and his family. Photo courtesy of Mayor Leary.

Mayor Steve Leary and his family. Photo courtesy of Mayor Leary.

When asked about his future political aspirations, Leary responded, “Right now I’m focused on finishing up my final term as Winter Park Mayor. I enjoy public service. So I rarely say never to future opportunities that would allow me to work with others to help protect our regions past and plan it’s future.”


Randy Ross is a radio host and political contributor for Florida National News. |

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