City Commission Bios
Mayor Kenneth W. Bradley
Elected Mayor in March 2009, Mayor Kenneth W. Bradley is currently serving his first term.
Mayor Bradley was raised in Winter Park and his parents have been Winter Park residents for over 50 years. He is dedicated to working with both residents and business owners to make his home town the very best it can be.
Mayor Bradley is Senior Vice President and Administrator of Winter Park Memorial Hospital, a Florida Hospital, which is one of the largest hospitals in the United States. He formerly served as Chief Executive Officer for Florida Hospital Kissimmee, Chief Operating Officer for Florida Hospital Celebration Health, and Chief Operating Officer for Florida Hospital Kissimmee. In addition, Mayor Bradley previously worked in human resources as the Wage and Benefits Analyst, Compensation Manager and Assistant Director. He has been with Florida Hospital for 25 years, and four generations of his family have served Florida Hospital more than 160 years collectively.
Mayor Bradley received his Master’s of Business Administration from the University of Central Florida, Orlando, and his Bachelor of Arts degree from Southern Adventist University, Collegedale, TN.
As a community builder and dedicated volunteer, Mayor Bradley serves on the boards of several organizations:
- Board member of the University of Central Florida Foundation
- Southwest Volusia Health Care Corporation Board of Trustees
- Rotary Club of Winter Park member
- Member of the American College of Healthcare Executives
- Appointed by the State of Florida CFO in 2006 to serve on the Florida Medical Malpractice Joint Underwriting Association
- 2007 graduate of Leadership Florida.
- Appointed in May 2006 by the Orange County Commission to the Metroplan Regional Transportation Citizen’s Advisory Committee
- 2004 chairman of the board, Winter Park Chamber of Commerce
- 1999 board chairman of Community Vision of Osceola County
- 1995-2001 Heart of Florida United Way Board member
- State Executive Committee member at Seventh-day Adventist for 12 years
Mayor Bradley has received numerous awards and recognitions including:
- 2010 Orlando Business Journal's Most Influential Businessman in Healthcare
- 2009 winter Park Chamber of Commerce "Citizen of the Year"
- 2007 Orange County Public Health Department “Healthcare Hero”
- 2007 finalist for Florida Medical Business “Best Hospital CEO”
- 2004 Orlando Business Journal’s Ten Most Influential Businessmen
- 2000 Leadership Osceola’s “Distinguished Leader” Award
- 2000 Kissimmee/Osceola Chamber Hispanic Business Council “Amigo” Award
- 1999 Orlando Business Journal “Forty under Forty” Award
During his spare time, Mayor Bradley enjoys golfing, traveling and spending time with his wife, Ruth.
Commissioner Carolyn Cooper

Elected City Commissioner (Seat 3) in March 2010, Commissioner Cooper is currently serving her first 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 and 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 ambience 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 Steven Leary
One of six children, Commissioner Leary was raised in Rye, N.Y. and attended The Brunswick School in Greenwich, Conn. He graduated from Washington College, Chestertown, Md., in 1989 and began working in the advertising business in New York City shortly thereafter. Commissioner Leary has worked for NW Ayer, Ammirati & Puris and J. Walter Thompson, among others, for clients such as De Beers, Miller Brewing Company®, Unilever, United Parcel Service®, Compaq Computer and Merrill Lynch.
In 1998, Commissioner 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 moved to Winter Park, Fla., to join his brother Bill, a longtime Winter Park resident. Together they own Leary Management Group. With 40 employees, they manage a group of family-owned properties across Central Florida. Their portfolio includes a community of 925 homes in Kissimmee, Fla., historic landmarked properties, and over 100,000 sq. ft. of Florida retail space between Orlando, Kissimmee, Mt. Dora, Haines City and Winter Park.
Commissioner Leary’s various leadership positions in large and small companies, managing budgets in excess of $100 million, and experience in restructuring and launching new divisions in New York, California and Florida should serve him well in helping to oversee and steer the City of Winter Park. Also, as a fairly recent transplant to the area and as someone that has spent years working within creative enterprises, the Commissioner believes that the best ideas for our city can come from anywhere - whether you have lived here for five days or five generations, whether you live on the Westside, Eastside or lakeside. He will engage residents, businesses, city staff and guests to develop and implement plans to maintain the charm, character and quality of life that originally attracted him and his wife to Winter Park.
Commissioner 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, Winter Park Chamber of Commerce and multiple youth activities in the area
Commissioner Tom McMacken
Elected City Commissioner (Seat 4) in March 2010, Commissioner McMacken is currently serving his first term as City Commissioner.
Commissioner McMacken has been actively involved in the city since moving to Winter Park 19 years ago. During that time he has served on and chaired four city boards: Planning & Zoning, Tree Preservation, Public Art Advisory and Historic Preservation. He has also served on the Park Acquisition Task Force and assisted the city in updating the landscape and irrigation codes. In addition, Commissioner McMacken has served on the Winter Park Autumn Art Festival since moving to Winter Park.
A landscape architect, Commissioner McMacken has been involved with the design of numerous projects in Winter Park including Winter Park Village, the Park Avenue streetscape and the park at Orwin Manor.
Commissioner McMacken and his wife Ann have a daughter Emily and he is a member of The First United Methodist Church of Winter Park.
Commissioner Sarah Sprinkel
There is an air of excitement that surrounds Commissioner Sprinkel and everything she does. Perhaps it is because of her belief that educating children should be exciting. Perhaps it is because of the tangible results her extensive knowledge of early childhood education has produced for many thousands of students.
In her current position as Senior Associate of Florida Services for Florida Virtual Schools (FLVS), Commissioner Sprinkel generates a new enthusiasm for the potential of online learning. Her assignment includes planning goals, objectives, activities and timelines for FLVS’ launch into elementary education. To perform that job, she brings insights gained as both a classroom teacher and a program manager. Prior to joining FLVS, Commissioner Sprinkel provided oversight of early childhood programs for Orange County Public Schools for 23 years. She is equally proud of the 10 years she spent teaching at the kindergarten level.
Additional previous assignments include, creating childhood development centers for
Walt Disney World®, creating family outreach programs for the Orlando Museum of Art, serving as a vice president for the YMCA, and providing private consultation services for social service agencies. She also lobbied with the Florida State Legislature on behalf of the needs of students.
Commissioner Sprinkel is constantly motivated by a desire to educate young people. Her commitment to her students and her profession finds the perfect setting in a virtual school dedicated to excellence. She earned her Master of Arts degree in Early Childhood Education from Rollins College in Winter Park. Her Bachelor of Science degree in Elementary Education was awarded by Lipscomb University in Nashville, Tenn.
Always a dedicated volunteer in her community, Commissioner Sprinkel has served on numerous boards, professional associations and committees over the years. She and her husband George have three children: Clark, Caroline and George. Her free time is spent enjoying the golf course and tending to her gardens