Mayor Steve Leary
Term ends March 2021

Mayor Steve LearyOne of six children, Mayor Leary was raised in Rye, N.Y., and attended The Brunswick School in Greenwich, Conn. Steve graduated from Washington College, Chestertown, Md., in 1989 and began working in the advertising business in New York City shortly thereafter.

In 1998, Mayor Leary helped launch the interactive marketing group digital@jwt. From there, he was recruited to San Francisco in 2000 to help restructure a technology start-up, eventually moving back to the NYC area. In 2004, he and his wife Caroline chose to move to Winter Park to start their family.

Mayor Leary is the Owner and President of Flange Skillets International, a local small business that manufactures and markets gasket positioning devices to the oil & gas pipeline sector. Steve is also a partner with his brother Bill in Leary Management Group. With 26 employees, they manage a group of family-owned properties across Central Florida.

Prior to being re-elected Mayor in 2018 for his second term, Mayor Leary was first elected to Seat 1 of the Winter Park City Commission in 2011, reelected in 2014 with no opposition, then served his first term as Mayor in 2015.

Mayor Leary and his wife Caroline are the proud parents of Alexandra, Jack and William, triplets born at Arnold Palmer Hospital in 2005. They are also active members of St. Margaret Mary Church, Winter Park Public Library, Community Coordinated Care for Children (4C’s), Winter Park Chamber of Commerce and multiple youth activities in the area.

Commissioner Marty Sullivan
Term ends March 2023

Commissioner Marty Sullivan

Commissioner Sullivan is a 5th generation Floridian and professional engineer, as were his father and grandfather. He grew up in Tampa and moved to Winter Park in 1982, where he and his wife raised their daughter who was on the crew team at Winter Park High School. His wife, Maura Smith, is a lawyer and now retired from service as a judge on the Ninth Judicial Circuit Court. Commissioner Sullivan is retired from environmental and geotechnical engineering, having worked as a lead engineer on over 250 projects for private clients, as well as cities and counties across Florida.

Commissioner Sullivan earned an undergraduate degree in physics from the University of South Florida, and master’s degrees in economics at Florida State University, and engineering at the University of Central Florida. He is also a Unites States Navy Veteran.

Commissioner Sullivan’s service to Winter Park includes serving as chair of the Utility Advisory Board, Stormwater Board of Appeals, and Pedestrian & Bicycle Advisory Board as well as serving on the Transportation Task Force and Lakes & Waterways Advisory Board. His service to the metropolitan area includes being a member of the Orange County Public Works Advisory Board, MetroPlan Orlando and chair of the MPO Bicycle & Pedestrian Board. Statewide service includes serving on the Florida Conservation Coalition Steering Committee, Statewide Natural Resources Director and League of Women Voters of Florida.

Commissioner Sullivan’s hobbies include building kayaks, paddleboarding and camping the wilderness coasts of Florida, fishing, music and civic activities.

Commissioner Sheila DeCiccio
Term ends March 2023

Commissioner DeCiccio

Commissioner DeCiccio is an attorney, community volunteer, wife and mother who has lived in Winter Park for 37 years.

Commissioner DeCiccio earned her law degree from the New England School of Law. She began her legal career in Boston as an Assistant District Attorney handling felony cases.  As an ADA, Commissioner DeCiccio honed her skills of digging into the facts and conducting in-depth research to prepare for trial.

In 1982, Commissioner DeCiccio and her husband Dan moved to Florida. Sheila joined the Lowndes Law firm where she became the firm’s first woman partner.  At Lowndes, Commissioner DeCiccio was a litigator who worked in state and federal courts.

In 1993, Commissioner DeCiccio joined her husband at the law firm of DeCiccio & Johnson Law on Morse Boulevard.  She has enjoyed practicing law as well as her role of being a small business owner in Winter Park.

Commissioner DeCiccio is a member of the Winter Park Rotary, Winter Park Land Trust, Council of 101 with the Orlando Museum of Art, Albin Polasek Museum & Sculpture Gardens and Winter Park History Museum. For the past decade, Commissioner DeCiccio has served on numerous Winter Park city boards including the Planning & Zoning Board, Economic Development Advisory Board, chair of the Code Compliance Board, and Avenue Overlay Redevelopment Task Force.

Commissioner DeCiccio and her husband Dan have two grown children, Emily and Daniel.  She and Dan enjoy the lakes, parks and overall charm of Winter Park where they chose to raise their family.

Commissioner Carolyn Cooper
Term ends March 2022

Commissioner Carolyn CooperElected City Commissioner (Seat 3) in March 2010, Commissioner Cooper is currently serving her fourth term.

In her early career, Commissioner Cooper served as a Department of the Air Force civilian financial manager and project manager. Later, as Director of Contracts for Martin Marietta Data Systems, she negotiated multi-million dollar contracts and managed a staff of professionals.

Most recently, she has served on the Winter Park Planning & Zoning Commission and was a member of the Comprehensive Plan Task Force.

Commissioner Cooper has extensive professional education, including training in zero-based budgeting and cost/schedule control systems from the Air Force Institute of Technology. She holds a master’s in systems management from the University of Southern California, a master’s in guidance and counseling from Troy University, and a bachelor’s in management from the University of West Florida.

Growing up in a military family and working in the defense industry, Carolyn has traveled extensively and lived in major metropolitan areas. When she first visited Winter Park in 1988, she recognized the value of the charm of this community. She cares deeply about Winter Park and is dedicated to ensuring it grows in a manner that protects the ambiance of our historic downtown. She is committed to redevelopment of our underutilized commercial corridors, enhancement of our family neighborhoods, and protection of our historic resources.

Commissioner Cooper and her husband, Ned, have raised three of their five children in Winter Park. The family is active in the First United Methodist Church of Winter Park.

Commissioner Cooper will use her skills to mitigate risks and make disciplined decisions on behalf of Winter Park citizens.

Commissioner Todd Weaver
Term ends March 2022

Commissioner Todd WeaverCommissioner Weaver was elected to the City Commission (Seat 4) in April 2019.

As the fifth child of 10 children, Commissioner Weaver honed his skills for negotiation and compromise at a young age. Born in Dayton, Ohio, he spent his childhood in rural South Carolina and moved with his family to central Florida in 1972. Before enrolling in college full time, Commissioner Weaver spent four years as a tradesman and certified automotive technician.

Commissioner Weaver earned his Engineering degree at the University of Central Florida, graduated in 1983 with double majors in Mechanical and Aerospace Engineering.  He attended the University of Florida’s College of Veterinary Medicine from 1989 to 1991.

While the bulk of Commissioner Weaver’s career has been in the aerospace (airframe, rocket and gas turbine engines) and commercial aviation industries, he has a broad array of experience outside of aerospace.  His varied design projects include flight-training and entertainment simulators, clean-room factory design and construction management, the tornado for Universal’s Twister attraction, rooftop solar systems, and a space shuttle-borne lab experiment apparatus launched in 1996.  Commissioner Weaver authored multiple patents in the fields of aerospace and municipal infrastructure.

Commissioner Weaver founded and serves as president of two Winter Park-based companies: Weaver Engineering, Inc., a 23-year old engineering and consulting business, and TruGrit Traction, Inc. which engineers and manufactures wheels and traction devices for underground piping inspection robots.

As a 20+ year resident of Winter Park, Commissioner Weaver has volunteered his time and talents over the years to his community on the Orange County’s Lakes Advisory Board for four years and Winter Park Lakes and Waterways Board from 2010-2016; the last two years as chairman. One of Todd’s proudest accomplishments is the restoration of Lake Bell.  After the crash of the lake ecology in the late nineties, he provided the neighborhood leadership needed to restore the lake to a thriving wildlife habitat.

Commissioner Weaver holds a Florida Certified General Contractor license and has managed and built numerous construction projects. Among his many hobbies, he is a fruit and vegetable gardener and beekeeper.

Commissioner Weaver is an active member of Winter Park Rotary and the University Club of Winter Park as well as several other local and national organizations.

Scroll to Top