Return your Vote By Mail Ballot OR on March 9th VOTE HERE at WG Fire Rescue HQ at 1 E Cypress St. just off Dillard St.
Robert “Bobby O” Olszewski (Ol-shess-key) is proud to call Winter Garden home. "Bobby O" is a former Commissioner for the City of Winter Garden and a former State Representative. He has lived in West Orange County since he was two-years old where he was a product of Orange County Public Schools (OCPS).
"Bobby O" learned the value of education and integrity from his parents. His late father Bob was a former Captain in the United States Army and the Electrical Engineer for OCPS as well as a former Little League president and coach. His mother Rosie was a public school English teacher, formerly at West Orange High School and Dr. Phillips High School, retiring after 30-years with OCPS.
Much of Bobby’s childhood was spent playing sports with his brother Matt, also a Winter Garden resident, who is a former Orange/Osceola County State Attorney and a practicing lawyer. Bobby’s wife Allison (West), a lifelong West Orange County resident, is an OCPS Writing Coach and Teacher at Independence Elementary, previously serving at Spring Lake Elementary, where she won Teacher of the Year, and at Palmetto Elementary, helping move the school from a “F” to an “A” in one year.
Bobby and Allison volunteer at the Basilica of the National Shrine of Mary, Queen of the Universe and attend Resurrection Church in Winter Garden. Bobby and Allison additionally donate their time, treasure, and talents to numerous West Orange and Central Florida nonprofit and community service organizations. Bobby and Allison are the proud parents to their 4-year-old daughter Reagan.
"Bobby O" previously served as a Winter Garden Commissioner for the same District 3 from 2012 to 2016. He was elected in a special election to the Florida House of Representatives representing District 44 from 2017 to 2018. Olszewski is the former Chair of the Orange County Community Action Board and Vice-Chair of the MetroPlan Orlando Municipal Advisory Committee.
Olszewski is a graduate of the Winter Garden Citizen's Police Academy and, prior to being elected to the Winter Garden Commission, served on the Winter Garden Police and Fire Pension Board. He is a graduate of the Florida League of Cities' (FLC) Advanced Institute for Elected Municipal Officials and served as Vice-Chair for the FLC's state-wide Finance, Tax, and Personnel Committee. In 2018, the Florida League of Cities honored Representative Olszewski as one of only 17 (out of 160) state legislators with a Legislative Appreciation Award for his support of Home Rule and advocating for local cities (see next section).
Olszewski was the Chair of the Roper YMCA Board of Directors after serving two years as the Scholarship Campaign Chair. He additionally served Winter Garden on the board of directors of the Winter Garden Heritage Foundation, OCPS Montessori of Winter Garden Charter School Board (now Innovation Montessori), and the West Orange Chamber of Commerce, where he was a graduate of their Leadership West Orange program. He is also a graduate of the Orange County Public Schools (OCPS) Leadership Orange program.
"Bobby O" is truly homegrown, after graduating from Dr. Phillips High School he earned an undergraduate double major from the University of Central Florida in Radio/Television (B.A.) and Organizational Communication (B.A.), as well as two master’s degrees in Management (M.S.) from Embry-Riddle Aeronautical University, and Corporate Communication & Technology (M.A.) from Rollins College. Bobby also earned a Ph.D. in Business Administration from Northcentral University.
Bobby additionally served as an Adjunct Professor, teaching management, business, communication, and marketing courses for UCF, Valencia College, Rollins College and Barry University (among others) both in the classroom and on-line, having taught thousands of students throughout his career.
"Bobby O" is a business owner leading the Emerson Management & Consulting Group, Inc. as Managing Principal. He has 25-years of leadership and organizational management experience specializing in strategic partnerships, marketing communications, and economic development.
He has held influential leadership positions within numerous organizations and agencies as these opportunities have offered him the opportunity to work and partner with a wealth of outstanding leaders, brands, and companies in a variety of diverse industries throughout the United States.
I am enthusiastically running for Winter Garden Commission because of my passion for service in my hometown community. Together with our collective efforts, Winter Garden enjoys an incredible reputation but we are seeing development encroach on our quality of life. We improve this quality with preservation of our natural resources by putting residents and community first in managing our growth. I do not own any land in the city that needs to be developed and I will not make a dime off of any vote that will come before the Winter Garden Commission. I humbly ask for your vote on Tuesday, March 9th as together we make Winter Garden even better by putting "Residents and Community First."