Winter Park Mayor Steve Leary has quietly undertaken the transformation of that city from being Orlando’s most venerable suburb to being perhaps Central Florida’s most admired city for its future prospects and has done so in one of the toughest political environments in the region.
Leary ranks as the 23rd-most powerful elected official in Central Florida, in Florida Politics’ debut survey of Central Florida’s Most Powerful Politicians.
Along the way, Winter Park has begun efforts to expand and improve its parks and greenspace system with a huge new preserve purchase; spent millions to acquire and bury utility lines to harden against future hurricanes; passed a $30 million bond referendum for a new library and events complex; tightened zoning codes to all but eliminate high-density developments; cracked down on billboards, and preserved the Park Avenue downtown district.
All of that has come as development pressures and property values have kept Winter Park one of the region’s tightest markets, with powerful interests wanting in. The library relocation and development of “The Canopy” community center, downtown parking issues, and billboards all have sparked community controversies.
Somehow Leary has gotten through it all with enormous popularity. A commonly cited attribute: people like him.
“Mayor Steve Leary is an immensely popular mayor in a town known to be one of the toughest political landscapes in Central Florida,” said Dana Loncar, public affairs specialist at Consensus Communications. “He has proven there is a winning formula in Winter Park by balancing sensitive issues, getting things done, and not raising taxes.”
Leary, 52, who owns an oil and gas pipeline supply company and a property management company, was first elected to the City Commission in 2011 and was elected Mayor in 2015 in a close race. In 2018 he was re-elected in a crushing landslide over Jim Fitch that had shaped up largely as a contest between those wishing to strongly embrace Winter Park’s past and those wishing to follow Leary into a future.
This is Leary’s city to lead now. It’s going his direction.
“Steve Leary has been a true leader to the Winter Park community with a leadership that has embodied conservative values,” said Orange County Republican Chair Charles Hart.
In a region where Republicans are losing ground everywhere and an established generation of Republican politicians are aging out or battling each other over priorities, Leary is seen as a rising hope.
“Undoubtedly, more voters will learn about Steve Leary in the years to come,” Hart assured.