Winter Park City Commission candidate Steve Leary says he's ready to present a positive vision for the city's future.
WINTER PARK – Sometimes the urge to jump into the political arena is motivated by anger, frustration, outrage – the burning desire to stand up and insist you’re fed up with the status quo.
For Steve Leary, his campaign for the Winter Park city commission was born out of an entirely different attitude. He loves the city, thinks it has a great future, and is positive about the place where he lives. He’s also positive on the campaign trail.
“I’ve been knocking on doors, and I love it,” Leary said on Tuesday afternoon, while enjoying a sandwich and iced coffee from one of his favorite Park Avenue hangouts, Palmano’s.
“I’ve met so many really good people,” he said. “That’s been real refreshing. And people I don’t know have decided to grab one of my signs. They know I’m more positive.”
At a time when politics seemed fueled by anger – over taxes, government spending, unemployment – Leary is hoping to sway voters with an approach that emphasizes optimism, not pessimism, the desire to succeed rather than a quick jump to tear something down.
“I’m a positive guy,” he said. “I love being here. I’m going to be pro, not no. That’s always been my approach.”
Leary is running to replace Commissioner Phil Anderson, who is not running again for the District 1 seat. Voters will decide on Tuesday, March 8 between Leary and attorney Scott Callahan.
Leary said his upbeat vision for the city doesn’t mean he isn’t looking for some changes in the way the city does business, or that he hasn’t found fault in the way the commission has operated recently. Several issues prompted him to run, including the matter of dog poop.
He felt the commission wasted time and money on a proposed $40,000 plan to educate voters about picking up dog waste from city sidewalks.
“I want to get the city commission back to discussions on the future of Winter Park, not worrying about picking up dog poop on the sidewalk,” he said. “People that have dogs know how to pick up after their dogs. It was a waste of money.”
Leary is a businessman who operates the Vista del Lago manufactured home community on U.S. 192 in Four Corners, one of the earliest housing developments in an area now booming with new commercial plazas, residential subdivisions and timeshare developments. He also runs a Winter Park property management firm and has properties in Haines City’s historic downtown.
Leary, who moved to Winter Park in 2004, has won over a healthy number of endorsements while out on the campaign trail, including nods from the Orlando Regional Realtors Association, Mayor Ken Bradley, state Rep. Dean Cannon, Orange County Commissioner Ted Edwards, Winter Park Fire and Rescue, and the organization Save Our Parks. He credits that to his plan to help reshape the way the commission operates.
“I didn’t like what was going on,” Leary said. “I think the city commission was dragged into the day to day operations of city government, and that’s not what they’re supposed to do.”
The commission began micromanaging the city, refusing to allow the city manager and municipal employees to do their job.
“The city staff is demoralized,” he said.
Rather than manage, the city commission needs to sit back and work on a long term vision, he said.
“When I worked in New York, I ran advertising accounts,” Leary said. “I’m used to dealing with enterprise-level groups with $220 million budgets. I want constructive engagement. I want the city not being run by a small vocal minority that tells people how to think and how to act.”
With his business background, Leary wants to work with the business community, to hear their ideas and figure out what they need to succeed.
“We need to engage the citizens of the town,” he said.
That doesn’t mean he wants to change the basic character of the city, including the downtown around Park Avenue.
“I want to keep the downtown looking the same,” Leary said. “I love it here, it’s one of the reasons I moved here. But look at the Ravenous Pig,” he said, of the “American Gastropub” restaurant on Orange Avenue in Winter Park.
“It’s one restaurant that’s slowly transforming that block,” Leary said. “We should be providing incentives to the businesses that need help.”
Leary also believes a growing commercial base on roadways like Fairbanks Avenue, Orange Avenue and Lee Road could expand the city’s tax base and allow residents to get some property tax relief in the future.
“Seventy-five percent of our revenues come from individual property taxes,” he said. “We should be looking to diversify that number. If you’re going to revitalize Fairbanks, Lee Road, Orange Avenue, their taxes will help alleviate residential property taxes.”
He also wants the city to take a calm, measured approach to the $16 million unfunded pension liability, saying there’s time to work out a reasonable solution.
“The pension plan is 80 percent funded,” he said. “I wish my mortgage was 80 percent funded. I want to sit down and listen to people and figure this out together.”

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