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Winter Garden

He struck out at the county and state levels. Now Bobby O is back to re-claim the District 3 city commission seat he resigned in his quest for higher office

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Norine Dworkin

Sunday, March 7, 2021

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Paul Morrison/VoxPopuli

District 3 candidate Bobby Olszewski: "If I wanted higher office, everything was open [in 2020]. I said no."


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To sit with Bobby Olszewski — known as “Bobby O”; he doesn’t make anyone struggle with Olszewski (pronounced ole-shev-ski) — is to watch a seasoned politician at work. 

Even during our interview on a Starbucks patio, Olszewski works his brand of retail politics. He excuses himself to call out to people he knows, asking after their spouses. He shares that he’s knocked on nearly 1,000 doors, as of our meeting, speaking with voters face-to-face. He makes sure I know that he was endorsed by Orange County District 1 Commissioner Nicole Wilson. He tells me that he ran for Orange County Commissioner, skipping over the part where he quit Winter Garden’s city commission to do so, forcing the city to hold a special election to fill his empty seat. Olszewski stays relentlessly on message. There are points he wants to make about his opponent, Commissioner Mark Maciel, and he works them into our conversation at every opportunity he finds.

But between throwing barbs at his opponent, Olszewski also discussed planks of his platform — ethical leadership and public safety — along with getting businesses to comply with Covid-19 rules, smart growth and whether he still dreams of launching another run for higher office.

Norine Dworkin: So, how did you first get into politics?

Bobby Olszewski: I’ve always enjoyed following politics and I’ve always been involved in my community. I just got a bug, probably around 2008/2009, I started getting real involved. I started attending every Winter Garden City Commission meeting for three years before I ran. I got elected, defeated an incumbent [Commissioner Harold Bouler in 2012], and the rest is history.

In 2016, I ran for the Orange County Commission in District 1 and was very close, even though we were out-raised by all the developers and special interests. We came up a little short to Betsy VanderLey. [Olszewski vacated his Winter Garden District 3 commission seat to challenge VanderLey for her seat on the Orange County Commission.]

Then there was a special election in 2017 for the Florida House of Representatives, and I won that race. [Olszewksi served the last year of state Rep. Eric Eisnaugle’s term after he resigned to accept an appointment to the 5th District Court of Appeals.]

ND: Then you ran again for re-election?

BO: I did and came up 1 percent short. [Olszewski was defeated by Democrat Geraldine Thompson.]

ND: Why are you running again for city commission. Why not take another run for the Florida House or higher office?

BO: A lot of people have encouraged me. The one thing that has come up is I’m running for higher office, I’m ambitious, I’m a go-getter. Look at what just happened in 2020. We had every Orange County office open. Every one of them, from tax collector to election supervisor to sheriff to property appraiser. Val Demings’s seat for U.S. Congress was open. My old seat in House District 44 was open. Orange County Commission District 1 was open. So anyone saying that I’m running for higher office or I have that ambition, if I wanted higher office or if I wanted to climb the ladder, everything was open, and I said no.

I think when you’re at that level in Tallahassee and you’ve been almost at the county level, you see how you can help your community better as a city commissioner. You don’t have the partisan politics. It’s all about what’s best for the city. And the fact that I get to go home to my wife and daughter every day and know I’m making the community better for them, my brother and my three nieces who live in Winter Garden, it’s a special opportunity.

What really made me decide was … go down Beulah Rd. and you see all the development that’s happening in residential areas. The number one thing we heard in the Orange County Commission race and in the state house race was traffic, growth and development is out of control.

We saw it in our Orange County District 1 race. No one expected an incumbent Orange County commissioner [Betsy VanderLey] to lose the way she did. I think it’s because the development and special interests are influencing people. That’s why my campaign is focused on residents and community first. Yeah, it’s a tagline for a campaign, but it’s the truth and it’s what’s in my heart.

I never, ever had to recuse myself from any vote on the Winter Garden commission or in the state house because I had a financial matter in the vote. It’s shocking to me that someone could say I’m here to serve the people, and they’re recusing themselves from votes. I’m not a developer. I don’t have a land acquisition company. I’m not recusing myself on votes on the Winter Garden commission. I’m here to serve the people.

[See VoxPopuli’s Q&A with Olszekski’s opponent Commissioner Mark Maciel for his responses to these statements.]

There’s nothing wrong with growth. But it has to be smart growth. When an investor comes in and buys a piece of land, and they want to develop something, that’s great. We’re going to work with you to make sure it matches the unique charm and feel of our communities and make sure we’re putting residents and community first. Not seeing how big of a building we can have on a small parcel because you chose to make that investment. There’s a cabal out there that has their tentacles in these races, and they’re out for themselves not for the people. I’m proud of my record and my commitment has always stood for the people I’ve served as an elected official.

ND: To be clear, the Florida Legislature has no allure for you?

BO: I lost the race by 1 percent. It was a rough race. I looked at it hard. People wanted me to do it again. I did my own analysis of the situation, that district and what’s going on in Orange County and the politics at large in the nation, and I decided early on that the race wasn’t for me and my family.

I cherish the experience and the relationships that I have in the Florida House and the Florida Senate. I have a wonderful relationship with the current Speaker and the next two speakers — the speaker designate was my roommate. I think that having those relationships at the state level, being able to pick up the phone and get that phone call returned, helps Winter Garden.

ND: One of the biggest projects in District 3 right now is the revitalization of the historically Black neighborhood East Winter Garden. Plans call for new, affordable housing and a small commercial district in the heart of East Winter Garden at Center and Tenth Streets. As commissioner, what would you do to bring new businesses into East Winter Garden?

BO: I think it’s all about the relationships you have to open up opportunity. In the past, we’ve had groups come in, like Matthew’s Hope and West Orange Habitat for Humanity to help individual residents. We have a lot of churches in East Winter Garden. But we do need some commercial projects.

The one thing I believe is that government can invite opportunity, but then it has to get out of the way and let the people who run the businesses help themselves and run their communities. At the same time we need to have that infrastructure in place. We have to incentivize the residents and businesses to come into Winter Garden, particularly if the city owns property, and they do in East Winter Garden. We have to make sure we have the right businesses and the right residential projects coming in that raises all boats.

ND: Let’s talk about your platform.

BO: The four issues I think are important are ethical leadership, fiscal responsibility, lower taxes and public safety.

The most important thing a government can do is keep their community safe. We’ve seen in the last year, a few more incidents than normal coming out of East Winter Garden, and that’s distressing. Being a private citizen, I haven’t been able to have the phone calls with [Police] Chief [Steve] Graham and other folks. But we have to make sure we’re investing in our police and fire to keep us safe because we are growing. When you are increasing your population and increasing your taxable base, not only residents but businesses and revitalization, that’s additional revenue coming into the city and that needs to be reinvested back into public safety and keeping our community safe.

My commitment has always been for law enforcement and making sure we’re fully funded and making sure law enforcement has what they need because we have a changing dynamic at all times as we’re growing and we need to be able to meet those challenges. Winter Garden is a safe community. I’m just noticing a couple more incidents in the past year in East Winter Garden.

ND: I did a story about East Winter Garden recently, and I asked Chief Graham about the corner at Center and Tenth Streets since that’s the focal point of the revitalization project. That’s also where people tend to congregate. He says there’s no real crime, nothing of note that goes on there.

BO:  That’s just a congregation point, and it’s actually gotten better than what it was when I first got into office. It’s a lot more discarded furniture and makeshift lounge areas and so forth. It’s gotten better, but it’s still the congregating point of that community.

ND: You’ve been walking through East Winter Garden. Do you see any other place to congregate?

BO: Not like that. No ma’am.

ND: So absent a place like Plant Street Market, the Crooked Can, Pilars or the Whole Enchilada or any place else for adults to gather and sit down and chat with each other, there’s really no other place for grownups to gather and socialize, is there?

BO: Right.

ND: It goes back to the revitalization project to put in some businesses where grownups can get together.

BO: That is true. One of the things I did as commissioner is I got the Zander Park playground there with swing sets. That’s something I heard a lot when I first ran, that they did not have any swings. I was the one that got that in there for them.

ND: I see that policing is a big part of your platform. As we’ve seen over the past year, there’s been increased focus on police brutality, particularly after the murder of George Floyd. I just heard on NPR, an officer in Ohio was responding to a non-emergency call. He saw a Black man coming out of his own garage holding up a cell phone and he shot him. Then the officer handcuffed him when he was down and refused to render aid. The officer has been charged with murder. I’m for protecting our community as well. I’m from New York City. I was there when the towers came down, so I have mad respect for first responders. But when I see police shoot unarmed Black men and pepper-spray a 9-year-old Black girl, handcuffed in the back of a police car or slam a Black high-school girl to the concrete floor, that makes me wonder about the kind of people we are allowing to serve on police forces.

BO: I think it makes us all sick when we see these stories, whether it be rogue police officers or rogue teachers or rogue politicians or rogue factory workers —

ND: But we’re not seeing rogue teachers, we’re seeing police officers.

BO: I don’t recall an incident in Winter Garden, and I will be the first one if a police officer is wrong to be against them. But I’ve not seen that being a problem in Winter Garden.

We talked about why I’m running — because you can impact your local community better. We don’t need Washington style politics coming in here to Winter Garden. Those issues are national issues and they need to be addressed. At the same time, you can only manage what you can manage, and as a Winter Garden commissioner I’m going to pray that on both sides of the aisle, I mean on both sides of the situation, for the victim and for the police officers — because there are police officers who are attacked too, it’s not a one-way street.

But I’m grateful that we live in Orange County, that we live in Winter Garden, that we haven’t seen the kind of stories that we’ve seen across the nation and that’s a good thing. But that doesn’t mean we rest on our laurels. We have to be ever-vigilant to be sure our police officers are getting the funding, and when I say funding, it’s not toys, it’s training and making sure we have the opportunity to help them deal with situations so they don’t ratchet it up.

I feel we do have a good police force, we do have a good fire force, and I have not heard of that problem ever as a Winter Garden commissioner, in the Orange County race or as a state house member, thank God. But it only takes one.

ND: I ask because of your emphasis on policing.

BO: It’s the fourth thing I list. My emphasis is on ethical leadership. That’s the most critical issue that we have in the Winter Garden commission race. I’ve given myself to public service. I don’t come from money. My parents weren’t politicians. They weren’t anointing me. I’m not a trust-fund baby. Everything I’ve gotten has a been because my mom and dad loved me and gave me the tools to go out on my own. I think that’s important because we see a lot of folks in government, what I call “silver spoons." They’re carrying on the legacy, “My Dad or My Mom Was the Mayor of …”

ND: Sure. Just look at our ex-president. He got everything from his father and he blew it all several times. And brought his own kids into politics, into the White House. Your point exactly.

BO: I wish I had that opportunity to have a safety net. But I think it stops good people from running. Again, I’ve never recused myself from a vote on the Winter Garden commission nor in the state house because I had a financial interest in the business coming before the elected body I was elected to serve on. Like I said, I’m not a developer. I’m not a land acquisition company. I think we have a big lesson with what happened in our Orange County commission race in 2020. People just don’t have the appetite for developers serving on elected boards.

ND: I think after four years of the Trump Administration, I think the country at large has lost its appetite for corruption.

BO: I would agree.

ND: Let’s talk about Covid-19. Winter Garden is in the position of so many cities across the country, trying to balance the needs of its businesses with the safety of its citizens. We’re kind of stuck between a rock and a hard place because of the rules that Gov. Ron DeSantis has imposed in terms of mask-wearing and on-premise dining. I know the city worked very hard to build Plant Street to make it the kind of destination it is. In city commission meetings, there’s a commissioner who always says how proud he is that no businesses on Plant Street closed during the pandemic. And yet among Winter Garden residents Covid-19 cases are rising. If you’re elected commissioner, what can you do to keep residents safe?

BO: You brought up two points. You mentioned one commissioner who was proud of the fact that on Plant St. there were no businesses closed. That was always my frustration on the Winter Garden commission. I’m a Winter Garden commissioner. I serve the people of Winter Garden. I don’t just serve the people in one district or who have their businesses on one street. That’s always been frustrating. You can’t live and die from what happens when you go to one place and your little bubble is going from your house to Plant St. to City Hall and that’s all you see. That’s a sad commentary.

I wear my mask in public. I’ll wear my mask during city commission meetings. The most important thing that comes up in local races is home rule. Home rule is allowing the cities and municipalities closest to the people make the rules that are best for them. And I think Jerry Demings has done that on the county level [with the mask mandate], saying, “This is what we need to do.”

When I go to downtown, I see the signs. I see what the rules are. I think it’s getting the businesses owners to commit to keeping their customers safe. Ultimately, the business owners, working with city government, need to decide what they want to do.

ND: And what of the business owners who won’t comply? Or who only do a token attempt of complying?

BO: That’s where the problem lies. The government sets the level playing field and allows the businesses to compete in the open market, but that’s not right when we have a company or business purposely violating what’s county law. I would have the ability to talk to Jerry Demings, working with [Winter Garden] Mayor [John] Rees, working with our city manager trying to find what the best scenario is. If a citizen brings me that problem, it’s my responsibility to find a solution. Since I’ve not been in the trenches, I need to get up to speed on what’s been done, and more importantly, look to the future to make it better, not just accepting the status quo and rubber stamp it.

ND: Commissioners make appointments to the committees and boards that help the commission run the city. These committees and boards are largely white and mostly male, while Winter Garden is now 53.6 percent non-white. How would you work to bring more diversity to these committees and boards?

BO: We can get more folks involved. I know there are a lot of folks in East Winter Garden that are fired up, that love their community that we could include. And I think when those spots become open, we as the commission can be made aware of that. I know when I was on there a lot of times you didn't know there’s even an opening or an appointment until you saw it in the agenda packet that’s set by the mayor and the city manager. So we need to encourage that.

I’ll make you a promise, when I’m sworn in on March 11, I will make sure I say that I want to encourage all minorities, people of color, females, and that we need more representation of the great diversity of the city of Winter Garden.

ND: When the City Charter came up for review, no one of color was on that committee and there were only a handful of women.

BO: You’re hitting on my number one point: ethical leadership. They have a good ol’ boy system. They’ve been after me in every race because they didn’t anoint me. My mom and dad weren’t members of the country club with them. We didn’t own an orange grove with them. They don’t like people that they didn’t “make” to use a mafia term. I’ve always been for the people. I’ve always been for what’s right.

When people ask why would you go back into this, I genuinely miss the service. When you have a constituent call you and say "I have a problem,” and they say “I’ve been trying for weeks or months and you’re the first person who’s called me back,” that's rewarding. And that’s what it’s about. It’s about public service. We’ve seen the good ol’ boy network, and we’ve seen it in Orange County, and we’ve seen it in Winter Garden, and we have to have ethical leadership.

The people of District 3 know Bobby O. They don’t know how to spell it, and I’ll sell you a few vowels if you’re buying. I’ve always been the one to fight for the little guy. I don’t have a huge house. I don’t drive a Mercedes. I love my family. I go to work. I try to make my world a better place and be a good son and brother and friend. But you’re an elected servant and you’re there to serve the people.

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