Candidate Bio

Steven Leary

Steven LearySteve Leary, Vice President of Leary Management Group, Inc., joined the firm in 2004 when he moved Winter Park. He is responsible for strategic planning and customer relations.

Leary was elected to the Winter Park City Commission in 2011 and was appointed Vice-Mayor by Mayor Kenneth Bradley. Leary has resigned his post as Commissioner in order to run for mayor, but will finish out his current term on the Commission. Depending on the outcome of the March 10 election, Leary will either succeed Bradley as Mayor of Winter Park or, if defeated, he will step down. 

Leary was raised in Rye, NY, and attended The Brunswick School in Greenwich, CT. He holds a Bachelor of Arts degree from Washington College in Chestertown, MD, is a licensed Real Estate Agent in the state of Florida, and is a graduate of Leadership Orlando Class #64. He served on the board of the Hamilton Holt School at Rollins College. Before moving to Florida, Leary worked in New York advertising for such firms as NW Ayer, J. Walter Thompson and Ammirati&Puris. 

His wife Caroline is founder of the architecture and design firm Studio Blue House. She and Leary have 10-year-old triplets. 

The Leary family supports Make-a-Wish, Community Coordinated Care for Children (4Cs) and Give Kids the World. They are active members of St. Margaret Mary Church, the Winter Park Public Library and the Winter Park Chamber of Commerce. 

Q: Why are you running? 

A: Winter Park is at an important juncture and our next Mayor, as the city’s CEO,needs abusiness background, an ability to bring people together as well as the ability to get results.  That’s who I am and that’s partly why I’m running.  I’m a business owner who employs 26 people. As Vice-Mayor, Ihelped craft fiscally conservative budgets, led the development and passage of Winter Park’s first-ever Urban Forestry Plan to preserve and protect our tree canopy for generations, helped secure $12 million in state funds to underground Winter Park power lines and $400,000 in state funds to revitalize Lake Lillian in Mead Gardens. The other reason I’m running is for our future generations. As the only member of the City Commission with school-aged children, I live with our future every day and believe we must make decisions with them in mind. 

 Q: What will you as mayor do differently? 

A: I will maintain our strict fiscal discipline. The city is in the most secure financial shape in its history, and I will ensure we do not go backwards.  As the driving force on the Commission behind the City’s recent and first ever Urban Forestry Management Plan, I will continue to push the implementation of the plan so this asset thrives for future generations.  I will strengthen our investment in our corridor plans so that regardless of where anyone enters our City they will feel like they are in the Winter Park we all know and love.  As the father of 9-year-old triplets, my family and I use almost every park and facility in the City on a regular basis.  I will expand our efforts to ensure each of these facilities, parks and buildingsis up to Winter Park standards.

 Q: What are the three most important planks in your platform? 

A: (1) Fiscally responsible budgeting

(2) Maintain a quality community through healthy trees, clean and less cluttered corridors and safe parks.

(3) Effective Community Involvement that gives a place at the table to the entire community in determining the future direction of the city. 

Q: What three things do you wish to change? 

A: (1) I would like a review of City Hall processes that impact the public to ensure that the processes are “citizen friendly” and transparent. 

(2) I will enhance our regional presence so that we have a “seat at the table” to ensure that Winter Park’s interests are protected in Central Florida’s growing region.

(3) I will engage the next generation of Winter Park leaders and connect them with today’s experienced leaders in a mentorship manner to ensure continuity across generations.

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