‘Bobby’ Olszewski files for Orange County Commission D1 seat

Winter Garden Commissioner Robert “Bobby” Olszewski filed Tuesday to run for Orange County Commission District 1.  

“I am excited to put our ‘Residents and Community First’ as I continue my passion for public service by representing our communities in District 1 as an Orange County Commissioner,” said Olszewski.

Olszewski Head Shot Print (4)“Orange County District 1 deserves genuine leadership as together we place the ‘Residents and Community First’ in Bay Lake, Dr. Phillips, Gotha, Horizon West, Hunter’s Creek, Lake Buena Vista, MetroWest, Oakland, Ocoee, Orlando, Tildenville, Williamsburg, Windermere, and Winter Garden,” said Olszewski.

“In Orange County growth is inevitable, but how you manage that growth is critical.   Look at all of the great things we have accomplished in Winter Garden with smart growth by putting our ‘Residents and Community First’ in the decisions that we made.”

Olszewski, who has lived in Orange County District 1 since 1980, was previously elected to two terms as a Winter Garden Commissioner, first elected by defeating the incumbent in a three-way race by 70% and winning his second term without opposition.   

Community Involvement:

Commissioner Olszewski has current/past affiliations as: Orange County Community Action Board Chair, MetroPlan Orlando Municipal Advisory Committee Vice-Chair, MetroPlan Orlando Regional Leadership Council, Roper YMCA Family Center Board Chair, Roper YMCA Scholarship Campaign Chair, FL League of Cities (FLC), Vice Chair-Finance, Tax, and Personnel FLC Policy Committee, Growth Management and Economic Affairs FLC Policy Committee, Advanced Institute for Elected Municipal Officials (FLC) Graduate, West Orange Chamber of Commerce Board, Full Sail University Sports Marketing & Media Board, UCF Alumni Government Relations Committee Knights Advocate, Leadership West Orange Graduate, Orange County Public Schools (OCPS) Leadership Orange Graduate, Winter Garden Citizen’s Police Academy Graduate, Tri-County League of Cities Advocacy Committee, Business Force Central FL Political Leadership Institute Graduate, West Orange/South Lake Transportation and Economic Development Task Force Board, FCSL Winter Garden Squeeze Advisory Board, James Madison Institute Central FL Board of Advisors, Tiger Bay Club of Central FL, OCPS Montessori of Winter Garden Charter School Board, Rotaract Club of Metro Orlando, Winter Garden Fire and Police Pension Board, Winter Garden Heritage Foundation Board, Florida Citrus Sports, Winter Garden Rotary, and the Downtown Athletic Club of Orlando Board.


Commissioner Olszewski earned a Ph.D. in Business Administration from Northcentral University and two master’s degrees in Management (M.S.) from Embry-Riddle Aeronautical University, and Corporate Communication & Technology (M.A.) from Rollins College.  He is an undergraduate double major from the University of Central Florida in Radio/Television (B.A.) and Organizational Communication (B.A.) where he is a Knight for Life UCF Alumni Association member.  Olszewski is a product of Orange County Public Schools (OCPS) graduating from Dr. Phillips High School.  


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