MEET THE CANDIDATE: Robert "Bobby" Olszewski

Robert "Bobby" Olszewski is one of four candidates for Orange County Commission District 1.

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Editor's note: These are the complete, unedited answers from Orange County Commission District 1 candidate Robert
"Bobby" Olszewski.

AGE: 38
FAMILY: Wife, Allison (West); expecting baby daughter, Reagan Lynne
EDUCATIONDr. Phillips High School; University of Central Florida, Double Major in Radio/Television (B.A.) and Organizational Communication (B.A).; Rollins College, Corporate Communication and Technology (M.A.); Embry-Riddle Aeronautical University, Management (M.S.); Northcentral University, Business Administration (Ph.D.)
Commissioner-City of Winter Garden, 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 Florida Political Leadership Institute Graduate, West Orange/South Lake Transportation and Economic Development Task Force Board, Florida Collegiate Summer League (FCSL) Winter Garden Squeeze Advisory Board, James Madison Institute Central FL Board of Advisors, Tiger Bay Club of Central Florida, 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.
Fraternal Order of Police (3,000 Orange County Law Enforcement Officers); BusinessForce (Central Florida Partnership and Chamber of Commerce); Save Orange County; Ministers Association of Central Florida; Florida State Senate President Andy Gardiner; Apopka Mayor Joe Kilsheimer; Windermere Councilmember John Armstrong; Windermere Councilmember Bob McKinley; Windermere Councilmember Jim O’Brien; Windermere Councilmember Al Pichon; Ocoee Commissioner Rosemary Wilsen; Apopka Commissioner Diane Velazquez; Clermont Councilmember Timothy Bates; Former Orange County Clerk of Courts Eddie Fernandez; Former Winter Garden Commissioner Charlie Mae Wilder; Former Winter Garden Commissioner Gerald Jowers; Immediate Past President of the Hunters Creek Community Association Bob Anders; Former General Manager (26-years) of the Hunters Creek Community Association John Rasnic
Winter Garden Commissioner Colin Sharman; Ocoee Commissioner and former Ocoee Mayor John Grogan; Florida State Rep. Randolph Bracy; Florida State Rep. Rene Placencia; Former Florida House Speaker Will Weatherford; Former Florida State Rep. Steve Precourt; Former Ocoee Commissioner Angel de la Portilla

This race is one of the most competitive in Orange County, and it also happens to be one of the most important to West Orange residents. There have been several negative advertising pieces sent to District 1 residents by more than one candidate. Evaluate yours — and the other candidates’ — campaigning processes. 
From day one, my campaign has been an issues-based and results-oriented campaign that lays out a vision for how we can put our “Residents and Community First” back in Orange County District 1.  I have detailed how together we will protect our economy, our community, our neighborhoods, our resident's pocketbooks, and our quality of life.  My opponent has been grasping at straws to try to derail our positive vision for Orange County, but that is to be expected based on the positive results our campaign has generated.  No matter what other candidates or groups do, I will continue to focus on our vision for Orange County and how we will put “Residents and Community First. “

Advertisements sent to District 1 residents have questioned your attendance record regarding the MetroPlan Municipal Advisory Committee. Please explain these absences.
The MetroPlan Municipal Advisory Committee (MAC) is just that, an advisory committee that does not have any actionable voting authority or power.  In fact, the last MAC meeting that I attended, I served as the MAC's Vice Chair.  When I learned that an elected official and fellow MAC member was using their vote on this committee to benefit their personal paycheck and benefit their clients, I was appalled.  I brought this to the attention of MetroPlan employee and MAC staff liaison Virginia Whittington and next I had a discussion with MetroPlan executive director Harry Barley.  I can only assume that Mr. Barley discussed this directly with MetroPlan Board Chair and Orange County District 1 Commissioner Scott Boyd.  Since the ethical voting concerns I had with the MAC fell on deaf ears, I contacted our Winter Garden Mayor John Rees and City Manager Mike Bollhoefer and informed them that I could no longer attend MAC because of this breaching the public's trust and they agreed. I can assure you when I am elected, we will stop the cronyism and corruption in every shade and color in Orange County and hold elected officials accountable as we put "Residents and Community First" back in District 1.

Editor's note: For more on this issue, see our story here.

West Orange County is one of the fastest-growing communities in the country. How do you balance that growth? What is smart growth?
When we put “Residents and Community First,” we make sure that smart growth is quality development that maintains the unique charm and feel of our neighborhoods.  We have an outstanding record in Winter Garden where our city has become the envy of the state, and even throughout the country, because of our community development efforts with a sense of place and purpose for our citizens.  Winter Garden residents have enjoyed the highest property value growth increase in Orange County over the past two years and that is achieved with planned, smart, and balanced growth.  As an Orange County Commissioner, I will ensure that development works proactively with residents in the community, much like we have done in Winter Garden where as a Commission, 99% of our votes have been unanimous because of the effort that goes into ensuring the projects will be beneficial to residents prior to voting on them. We truly make conscientious efforts for residents working directly with staff, developers, and community members. Additionally, part of balanced growth is making sure that we have parks and green space with interconnected trails, giving us a more walkable, connected, and inclusive community. Our community can trust that I will always look out for their best interest because my family does not own any land in the district that needs to be developed nor does my employer make a dime off any vote I make as I will always put “Residents and Community First.” I am proud to have the endorsement of Save Orange County which strives for smart, balanced, and planned growth in all of the communities in our county.

What would you do to maintain safety in West Orange as it continues to grow?
We unfortunately have seen first-hand tragedy in Orange County from senseless violence at Pulse as we continue to pray for the victims, their families, and our community under this intense international spotlight.  The most fundamental role for a local government is to protect the security of the communities it serves.  Having a sound and effective sheriff and fire departments benefit all communities to provide opportunities that can lead to success for our Orange County residents, guests, and businesses.  It is imperative that we continue to be proactive rather than reactive working closely with all of our local municipalities, along with state and federal agencies by supporting community policing programs.  We need to ensure that we give law enforcement all of the resources they need to keep us safe, including investing in body armor.  I am the only candidate in this race who is endorsed by over 3,000 brave men and women in law enforcement in Orange County through the Fraternal Order of Police. I am a graduate of the Winter Garden Citizen’s Police Academy and, as a Winter Garden Commissioner, our WGPD now handles all of the dispatch services for Windermere, Ocoee, and Oakland because of our strong public safety results and resources.

What would you do to increase jobs in West Orange? 
I have the academic, professional, and political experience to create new opportunities for West Orange County residents.  I am proud to have the endorsement of BusinessForce, the political arm of the Central Florida Partnership and Chamber of Commerce, as the pro-business candidate for Orange County District 1.  Having worked with a number of agencies in diverse business development activities, as well as a college adjunct business professor, it is imperative that we focus on creating a community that can attract businesses and jobs to West Orange County.  As a Winter Garden Commissioner, I worked closely with the cities of Apopka and Ocoee in our Tri-City Partnership to increase economic development outcomes for our corridor.  For example, look at what we have accomplished in Winter Garden with Florida Hospital by adding a large employer, which has created many new jobs, as well as new small businesses in the medical field which fits the unique charm and feel of our community. Florida Hospital Apopka is currently under construction just a few miles away on the 429.  Additionally, Orlando Health continues to expand at Health Central with their new tower, in addition to starting construction on a new hospital in Horizon West. By working proactively with large employers, we expand our opportunities for increased jobs and new small businesses.  Also, with my background in higher education, I will work proactively with the University of Central Florida, Valencia College, and Orange County Public Schools to ensure educational opportunities are available right here in our community so our residents have access to highly skilled training and increased opportunities for our skilled workforce.  

After tourism, what should be the second-largest economic driver in West Orange?
Together we must manage Orange County resources by focusing on maintaining a sense of community in making development decisions. The focus from our latest business trends in West Orange is on healthcare.  There is no question that tourism is vital to our community as this true economic development engine creates more opportunities for healthcare services for our residents and visitors alike.  However, we can maintain our standing as the top tourist destination in the world while maintaining the sense of community in our neighborhoods for our residents. We do not have to sacrifice quality of life in our neighborhoods while we attract new businesses into Orange County by focusing on healthcare services with all of the hospital expansion in our community from both Florida Hospital and Orlando Heath. There are many small businesses coming to West Orange because of our community’s investment in healthcare. 

What is the greatest problem facing District 1, and what are your solutions to that problem?
Crime, Congestion, and Cronyism.  Orange County must ensure that we will continue to work together with our sheriff and fire departments and all municipalities in the county to ensure the safety of our family and property. It is always distressing to hear about a crime against a resident or business that could have been prevented. As an Orange County Commissioner, I will work to ensure the protection, security and safety of our residents and property. Safety also means keeping our commutes to and from our homes safe by being proactive rather than reactive.  I will ensure that decisions will be made to avoid seeing how many more cars we can fit into already over-crowded roads, because I serve the people. I do not have any voting conflicts benefiting my employer or land that is owned by my family and friends as I will always put “Residents and Community First” in Orange County. As an Orange County Commissioner I will do everything in my power to stop the cronyism and corruption by giving our community a voice providing a more transparent local government. 

Communication between the Orange County Commission and the Orange County School Board will continue to be important as West Orange continues to grow. As District 1 commissioner, how would you work to ensure the two entities cooperate and communicate?
I am a proud graduate of Orange County Public Schools (Dr. Phillips High) in addition to being an OCPS Leadership Orange program graduate for community leaders.  My wife Allison is a Teacher and Reading Coach at Independence Elementary in Horizon West and my mom Rosie, just retired after 30 years with OCPS teaching at West Orange High and at Dr. Phillips High since it opened.  My father Bob was the Electrical Engineer for OCPS when he passed away.  Suffice to say, OCPS has played a large role in my family’s life and I have a great working relationship with our OCPS School Board Members and staff.  Education is important to me as I have two master’s degrees and a Ph.D. in addition to serving as an adjunct college professor.  I hear daily the issues that face our children as we need to ensure that we are working together proactively doing what is best for our children.  I had a front row seat when my constituents at West Orange High had their children eat lunch at 10:30 AM because of an overcrowded school because elected officials were playing both sides of the issue regarding the relief high school.  I will work proactively with OCPS and Orange County staff to ensure that we get schools out of the ground faster while maintaining new schools share the unique charm and feel of our neighborhoods.  With my strong academic background, Orange County residents can be assured that I will do everything I can to ensure our children have a positive learning environment in which we all can flourish for generations to come.

Evaluate the work of outgoing District 1 Commissioner S. Scott Boyd. If you had to assign Boyd a letter grade (A to F), how would you grade him? Why?
I truly thank Commissioner Boyd for his service in Orange County District 1.  In his first term, Commissioner Boyd performed admirably.  Unfortunately, the vast majority of his second term he was too focused on anointing his successor as well as setting himself up to become Orange County Property Appraiser before he dropped out to now run for Orange County Mayor.  Additionally, too many municipalities and unincorporated areas did not get the attention they deserved because of his emphasis on an area of our district with all of the well-funded development interests.  It is not just how you start, but also how you finish, so I would give him a C.

If you were elected, what would stay the same under your leadership?
The Orange County District 1 boundaries are not changing as it will be the same geographic district that we have seen for the last eight years.  I look forward to putting “Residents and Community First” as we keep our community safe and maintain the unique charm and feel of our neighborhoods.

If you were elected, what would change under your leadership?
As an Orange County Commissioner I will work proactively with communities and homeowners associations to ensure that we are working through issues before they are problems.  I would not transmit projects just because a developer has asked me to and then have multiple community meetings pretending to get community input when the deal is already done.  I will put “Residents and Community First” and work proactively with residents, listening to their concerns, and developers to ensure that we maintain the unique charm and feel of our neighborhoods with planned, smart, and balanced growth.

What differentiates you from the other candidates for this position?
I have the political, professional, and academic experience to hit the ground running to best serve as your next Orange County Commissioner in District 1.  I have my own record of accomplishments where I do not owe any individual or group any special favors.  My concern is always with the people who elected me, ensuring that we put “Residents and Community First” in Orange County District 1. 

What qualities or skills do you bring to this position?
My compass is always pointing North.  I strive to do the right thing for everyone as a man of Faith.  I am a good communicator, who lives his life openly and honestly, and whose heart is on their sleeve.  If I can help, I will, if I cannot, I will let you know why and where we might be able to find some help. I am an elected Winter Garden Commissioner serving diverse communities and working with many different groups to make our community a better place.  Political, professional, and academic experience matters as I will ensure that our community’s needs are met by placing “Residents and Community First.”

Why are you the best candidate?
This community is my home. I have lived here since I was two growing up in the Dr. Phillips and Windermere communities and plan on raising my family here in Winter Garden.  My deep roots in the community help guide my decisions because I want to make sure all choices we make continue to make District 1 such a special place.  I am running on my own record and have already been tested as a Commissioner for the city of Winter Garden, the third largest city in Orange County with almost 40,000 citizens.  I have had political, professional, and academic leadership positions in which to draw upon years of experience to put “Residents and Community First” immediately when elected as our next Orange County Commissioner for District 1.  I would be honored for your vote on August 30 and please visit for more information.


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