Winter Garden Commission Candidate Q&A: Robert 'Bobby O' Olszewski, District 3

Robert 'Bobby O' Olszewski is one of two candidates running for Winter Garden Commission District 3.

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  • | 12:16 a.m. February 11, 2021
Courtesy Robert 'Bobby O' Olszewski
Courtesy Robert 'Bobby O' Olszewski
  • West Orange Times & Observer
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Age: 43

Family: Wife, Allison, and 4-year-old daughter, Reagan

Education: Dr. Phillips High School; University of Central Florida; Master’s degree, Rollins College; Master’s degree, Embry-Riddle Aeronautical University; Ph.D., Northcentral University

Experience: Former Winter Garden commissioner for District 3; former state representative in the Florida House of Representatives; chair of the Orange County Community Action Board; managing principal of Emerson Management and Consulting Group, Inc.

Why do you want to serve as District 3 commissioner?

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 on this quality with preservation of our natural resources by listening to residents and not developers in managing our growth, while investing in green spaces and our environment.

If you are elected, what do you hope to accomplish as a commissioner?

Drive down Beulah Road and you will see a great example of development encroaching into our residential communities. This is what happens when developers have too much influence on our Winter Garden Commission without regards for the unique charm and feel of our neighborhoods. I will ethically manage the city’s budget and future growth by focusing on maintaining a sense of community in making development decisions that put residents in charge and not the developers and special interests. We can still maintain our standing as the top destination along the West Orange Trail while strengthening the sense of community in our neighborhoods for our residents with revitalization efforts in those areas that need extra attention. I will continue to promote Winter Garden as a viable solution for businesses to thrive well into the future by always looking at the long-term impact for our residents first and foremost. I will additionally make sure we fully fund our police and firefighters who are on the front lines daily, keeping our communities and properties safe.

Why should District 3 residents vote for you?

My passion and dedication to our Winter Garden community is genuine. By the time this is in print, I will have personally knocked on over 2,500 doors in District 3. Our residents deserve ethical leadership in all matters related to all of our city’s communities. I have never voted for a tax increase or raised the (millage) rate for Winter Garden residents. I do not own any land that needs to be developed. I will not make a dime off of any vote that will come before the Winter Garden Commission. My record is rooted in dedication to the residents through ethical service to our community through smart, managed, community-principled and resident-centered growth. I have solid relationships with leaders in the state legislature, as well as in Orange County. … These relationships can only benefit our residents and help Winter Garden thrive into the future.

What are your thoughts on Winter Garden’s approach to managing or accommodating growth within the city?

Our community will not solve its problems counting on government, but instead from the innovation and ingenuity of its own local private businesses and residents by demanding accountability. It is important to have the faith of the people, as I will foster a positive culture on our Winter Garden Commission to make sure you are the top priority while engaging all residents and the communities in the decisions that affect our well-being, not the special interests. There is a right and wrong: A project fits our unique charm and feel of our community, or it doesn’t. We take pride in our quality of life by having a safe community, promoting education within our local schools, and building a community for current residents as well as future generations. 

What are some potential solutions for managing traffic conditions in conjunction with the city's growth?

When we develop future plans, we need to implement multiple modalities of transportation instead of a reliance on just automobiles. In the immediate downtown area, as well as the new plans for Dillard Street, we do see solid walkable and bike-friendly solutions. Unfortunately, most of Winter Garden does not have access to modes of travel other than their cars. We are not getting any commuter rail service, so we have to focus on making sound transportation decisions when it comes to our future development. Developers have only one place to build in Winter Garden, and that is up. We need to ensure that we are not growing with vertical towers that do not fit the unique charm and feel of our communities, increasing traffic and congestion.  

What are the top challenges you believe the city of Winter Garden faces? What are some potential ways to address them?

First and foremost, we need to be sure we are leading our way through the COVID-19 pandemic. We must keep our residents and visitors safe. There is a balance of making sure that we can get our community vaccinated while at the same time ensuring that we have a thriving economy to help provide for our families. Having solid relationships with local Orange County government leaders, the state Legislature (and) the governor's office, we will be able to collectively work together to rise stronger from the pandemic. We also need to be sure that we have ethical and transparent leadership working with neighboring municipalities and Orange County to solve our collective issues. 

If you had a magic wand, what three issues for Winter Garden would you change immediately?

One of the great things about living in Winter Garden is being so close to Walt Disney World and Universal Studios where we really do have access to magic wands! The first issue would be the complete revitalization of the east Winter Garden community as the anchor for the entry into Winter Garden from the 429. Next, with our city rapidly approaching 50,000, I would increase diversity and equitable representation with the involvement on our volunteer boards and city operations. Lastly, I would create official city of Winter Garden social media accounts on multiple social media platforms to promote our entire city, events and business beyond Plant Street. Since I have a magic wand, I am going to add a fourth: I would work with Orange County Commissioner Nicole Wilson to clean up the Windermere Crossing neighborhood lake that has been neglected for years.

If elected, how will you ensure transparency and open communication with residents?

Throughout my public service, I have prided myself on being extremely responsive to my constituents. I have always given out my personal cell phone and have been active on social media. Transparency is critical for any public servant to have the trust of the people they serve. I have no personal financial interests that will be a conflict of interest in votes coming before the Winter Garden Commission. I serve the people and not the special interests and I will always put “Residents and Community First.”


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