City Commission Bios
Mayor Kenneth W. Bradley
Elected Mayor in March 2009, Mayor Bradley is currently serving his first term.
Mayor Bradley was raised in Winter Park and is dedicated to working with both residents and business owners to make his home town the very best it can be. His parents have been Winter Park residents for over 50 years.
Mayor Bradley is campus CEO of Winter Park Memorial Hospital, a Florida Hospital, which is one of the largest hospitals in the United States. He also serves as a senior vice-president for Florida Hospital and is on the Board of Trustees for the Southwest Volusia Hospital Corporation. He brings 23 years of Central Florida healthcare experience to his leadership role, with his professional roots in human resources management. His family has served Florida Hospital for four generations with over 158 years of total service collectively.
Mayor Bradley received his Master’s of Business Administration from the University of Central Florida and his Bachelor of Arts degree from Southern College of Seventh-day Adventist.
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
- 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:
- 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.
Vice Mayor Karen Diebel
Elected City Commissioner (Seat 3) in March 2007, Commissioner Diebel is currently serving her first term as City Commissioner.
Commissioner Diebel is an executive in a Fortune 50 company with a proven track record of sound decision making. She has a master's degree in business administration with a background in finance.
Having lived in Winter Park for the past 10 years, she recognizes the importance of the city’s parks, lakes, and heritage. Her successful seven-year campaign helped to establish the Howell Branch Preserve, Winter Park's newest passive park and wetland oasis. Her vision for the city includes the revitalization of Winter Park, improvement of communication with residents, and fiscal responsibility. Commissioner Diebel has three young sons, Conor, Liam, and Nicholas. They are active members of Saint Margaret Mary Catholic Church in Winter Park.
Commissioner Phil Anderson
Elected City Commissioner (Seat 1) in March 2008, Commissioner Anderson is currently serving his first term.
Commissioner Anderson served as chief operating officer for CNL Retirement Properties, a leading senior housing finance company, until October 2007 when the company was sold in a 5+ billion-dollar transaction. Prior to CNL, he was a senior vice president at Classic Residence by Hyatt® in Chicago. In both companies, he focused on financing and acquiring or developing senior living communities. Throughout his career, Commissioner Anderson developed a reputation for team leadership, consensus building, intelligent negotiation and disciplined financial transactions. He has demonstrated an ability to listen to all views, define win-win solutions and make reasonable, informed decisions with clarity.
Commissioner Anderson graduated from Georgia Tech with a bachelor's in civil engineering. As a co-op student, he worked his way through school with the Alabama Power and Georgia Power companies. Upon graduation, Commissioner Anderson joined Georgia Power as an engineer on various power plant projects.
In his volunteer work, Commissioner Anderson serves on a variety of national and international organizations that focus on senior housing and senior living issues. Locally, he serves at the First United Methodist Church on the finance committee. He and his children have enjoyed Indian Guides, helping to build a Habitat for Humanity® home in Winter Park and participating on a recent mission trip to Costa Rica. Commissioner Anderson has served on the University of Central Florida/Shakespeare Festival Board and secured sponsorships for several Christmas performances.
Commissioner Anderson’s family has its roots in Florence, Ala., but he grew up in the Philippines as a missionary kid. Commissioner Anderson and his wife, Jennifer, have four children and a supportive extended family in the region.
Commissioner Margie Bridges
Elected City Commissioner (Seat 4) in March 2007, Commissioner Bridges is currently serving her first term as City Commissioner.
Commissioner Bridges grew up in Winter Park and has a vast knowledge of the area. She has served on various citizen advisory boards including Planning & Zoning Board, the Tree Preservation Board, the Park Acquisition Task Force and the Historical Preservation Board and Task Force.
She also continues to be involved with the Neighborhood Council. Commissioner Bridges is committed to maintaining the feel and heritage of Winter Park and sitting on the city commission will be her full time job.
Commissioner Bridges raised four wonderful children with her husband in Winter Park and has four generations of her family living here.
Meeting Notices
Commissioner Beth Dillaha
Elected City Commissioner (Seat 2) in March 2008, Commissioner Dillaha is currently serving her first term. Commissioner Dillaha earned her bachelor’s degree in business administration from Ohio State University in Columbus, OH.
Beginning in 1994, she began working on Winter Park city advisory boards including Code Enforcement, Keep Winter Park Beautiful, the Parks & Recreation and Tree Preservation. She served as president of the Forrest Hills Neighborhood Association and is currently a board member of the Friends of Casa Feliz.
Prior to her community work, she had a career in sales, sales management and retail management with three major U.S.-based corporations in the pharmaceuticals, cosmetics and nutritional industries. Most recently, she assisted in the start-up of her husband’s Winter Park-based company, Performance Matters, a technology corporation in the education arena with an emphasis on improving student performance and student achievement in school districts throughout the United States.
Commissioner Dillaha is dedicated to listening to the citizens of Winter Park and to the establishment of growth management policies to ensure our quality of life is maintained and enhanced. A fiscal conservative, she is committed to making sound financial decisions on behalf of the taxpayers.