Five takeaways from Winter Park’s election

Five takeaways from Winter Park’s election

Five takeaways from Winter Park's election

Big turnout and big money helped drive this year’s elections

March 21, 2024

By Beth Kassab

Winter Park elected a new mayor and sent two of the Seat 2 candidates into a run-off set for April 16. Here’s five takeaways from the results:

1. Glass ceiling shattered. Sheila DeCiccio wasn’t the first woman to run for mayor in Winter Park, but she is the first to win the post in the city’s 142-year history. DeCiccio, an attorney who has lived in Winter Park for nearly 40 years, joins Eatonville’s Angie Gardner and Oakland’s Kathy Stark as the only other women mayors currently in Orange County. Orlando, the county’s largest city, hasn’t had a woman at the helm since Glenda Hood left office in 2003. DeCiccio, who was first elected to the Winter Park City Commission in 2020 and took more than 71% of the vote on Tuesday, said she is thrilled to bring a new era to the city. “I ran based on my experience and I didn’t make an issue out of being the first woman, but yes, it’s great to break the glass ceiling — it always is and I’m happy I was able to do it.”

2. Party politics not a sure thing. With the Republican presidential primary on the same ballot as the city elections for Republican voters, party politics might have seemed like a good strategy. Afterall, Donald Trump easily won every precinct in Winter Park. But the candidates who tried to seize on that tactic fared the worst. Registered Republicans slightly outnumber Democrats in the city (8,300 R’s vs. 7,700 D’s plus 5,200 registered with another party or without any party affiliation) but that didn’t translate to wins for those who tried to align themselves with the right. Stockton Reeves, who had text messages sent out by the state GOP touting him as “your OFFICIAL Republican nominee” in the nonpartisan Seat 2 race and who also sent out mailers that called out “higher prices and inflation” came in third out of three candidates. Michael Cameron, who ran against DeCiccio, used hashtags like “red wave” and “conservative” in some social media posts and spent most of his tiny campaign account on a Republican political consultant. The other thing Reeves and Cameron had in common? Neither showed for public candidate forums — perhaps an indication that talking directly to voters matters more than party in local politics.

3. The money matters. The size of a candidate’s campaign chest doesn’t always determine who wins, but it can count for a lot. In the Seat 2 race, Craig Russell was the top vote getter by 8 points with 42% of the vote and also spent the most or had the most spent on his behalf. Russell, a teacher at Winter Park High School, raised $64,000 and the political action committee affiliated with the local Chamber of Commerce raised another $22,000 to spend on mailers and other activities to support his candidacy. That’s a combined $86,000 compared to $45,000 raised by Jason Johnson, who received 34% of the vote. The two will head into a runoff on April 16 since neither captured more than 50%. But if money were the only deciding factor, then Reeves, who loaned himself more than $50,000 and raised another $20,000, would be in the runoff since he outraised and outspent Johnson. He took just 24% of the vote. In the mayor’s race, DeCiccio far outraised Cameron — more than $41,000 compared to less than $7,000, according to the latest financial reports.

4. Winter Park knows how to turn out. The city has a reputation for being among the most civically active in the county and that held true again. Overall turnout across the mostly blue county dipped by 8 points to 18% since the Democrats opted against a presidential primary vote in Florida (in 2020, the last time both parties had presidential primaries in March, countywide turnout was more than 26%). But Winter Park turnout held fairly steady at 31% compared to nearly 32% in 2020. Only the much smaller cities of Oakland and Eatonville brought out a higher rate of voters for municipal races this time around. In Winter Garden, municipal race turnout was just 8% while Ocoee and Apopka each showed 14%. And while Winter Park is Orange’s fifth largest city with 30,000 people, it saw the most voters with nearly 7,000 people casting a ballot. That figure included the highest percent of Democrats (31%) except for Oakland (35%), the west Orange city of fewer than 4,000 people.

5. Will turnout hold for the runoff? Turning out voters once is hard. Getting them to show up at the polls twice can be even more difficult. That’s why state and national numbers show fewer voters tend to vote in runoffs. But Winter Park’s engagement appears to buck that trend. The last time Winter Park held a runoff was 2019 when Todd Weaver beat Pete Weldon for Seat 4. A look at the numbers shows 726 more people voted in the April runoff than in the first March election — 6,129 vs. 5,403. No one knows what will happen this year, but a drop in participation is not a sure thing in Winter Park.


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Sheila DeCiccio is Winter Park’s next mayor

Sheila DeCiccio is Winter Park’s next mayor

Sheila DeCiccio is Winter Park's next mayor

Craig Russell and Jason Johnson head to run-off for Seat 2 on City Commission

March 19, 2024

By Beth Kassab

Sheila DeCiccio will be Winter Park’s next mayor — the first woman to serve in the role — after she won more than 70% of the vote Tuesday.

Her opponent, Michael Cameron, who barely raised any money and did not appear at a single public or private forum, took 29% of the vote.

DeCiccio, who was first elected as a commissioner in 2020, is known for pushing to shore up the city’s infrastructure in the wake of flooding after Hurricane Ian in 2022. She also played a key role in overturning the original Orange Avenue Overlay, which allowed for taller and denser development along Orange between Rollins College and U.S. 17-92.

She is the first woman to be elected to the post in the city of 30,000’s 142-year history. She won every precinct in Winter Park by a wide margin.

Two of the three Seat 2 candidates will take their heated contest into a run-off on April 16 after no candidate won more than 50 percent of the vote.

Craig Russell, a teacher and coach at Winter Park High School, won 42% of the vote and Jason Johnson, an attorney, took 34%.

Russell and Johnson have clearly staked out different positions on some issues.

Russell, who raised nearly $64,000 and was the only candidate endorsed by the Winter Park Chamber of Commerce, has said he is open to revisiting the original Orange Avenue Overlay as well as a series of charter amendments overwhelmingly approved by voters in 2022 that require a supermajority vote on the City Commission for certain zoning changes.

Russell did not immediately respond to a request for comment on the results.

Johnson, who raised $45,000, has said he supports the current OAO and doesn’t want to see Winter Park’s commercial corridors expanded or dramatically altered by new development.

“I fully expected this race to go into a run-off,” Johnson said Tuesday evening. “I’m happy to be one of the top two vote getters … There are certainly differences between myself and Mr. Russell and, as always, the voters of Winter Park will get the final say on who they want representing them in City Hall.”

Stockton Reeves, the third candidate in the race, won 24% of the vote. Reeves did not immediately respond to a request for comment.

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Ministerial Alliance video shows candidate differences on supermajority amendments

Ministerial Alliance video shows candidate differences on supermajority amendments

Ministerial Alliance video shows candidate differences on supermajority amendments

The interviews by Pastor Troy East showcase how candidates feel about preserving the city’s history and, specifically, what is left of the historically Black west side neighborhood

March 14, 2024

By Beth Kassab

The Winter Park Ministerial Alliance, a group of leaders from 10 of the city’s historically Black churches, announced Friday evening that it is endorsing Sheila DeCiccio for mayor.

The group, which posted to Facebook video interviews with three candidates running for office that highlighted some differences in their policy stances, is not making an endorsement in the Seat 2 commission race. (You can watch the video here.)

Pastor Troy East of New Hope Missionary Baptist Church asked questions of each candidate individually, focusing at times on their philosophies that could continue to reshape the city’s west side in and around Hannibal Square.

The area, which has been the target of a number of redevelopment projects and changed dramatically in recent decades, is historically Black dating back to the founding of the city in 1887.

Census data shows the city’s Black population has decreased in the last 30 years. In 1990, 2,988 of the city’s 22,000 residents — or about 13% — were Black, according to the U.S. Census. By 2000, the number dropped to just over 10%. In 2020, Black residents made up about 7%, or 2,140 of Winter Park’s population of nearly 30,000, the Census shows.

And Black voters make up the smallest share of city voters with about 1,233 of the nearly 22,000 active voters, according to the most recent statistics from the Orange County Supervisor of Elections Office.

Craig Russell (left) and Jason Johnson speak at a forum for Commission Seat 2 candidates at the Winter Park Library.

East asked the candidates for Seat 2 on the Commission what they would do to protect the history on west side.

“I do think the west side gets short shrift,” said Johnson, an attorney and first-time candidate who lives near Glen Haven Cemetery in the northeast section of the city. “The city of Winter Park would not exist but for two of the original residents of the west side … we’d be a neighborhood in the city of Orlando. I don’t think a lot of people know that. I didn’t know that before I met with residents on the west side.”

He went on to say he wants to try to preserve what is left of the community and cited, as one example, the recent groundbreaking at Unity Corner.

“The west side is a very valuable asset to this community and a rich part of our culture and history …,” he said. “Too often outsiders don’t realize it exists and how valuable it is to us … they think of the biggest homes on the lake and the fact that Carrot Top lives here and we’ve got Park Avenue … But the west side is an important part of this community and I’ll do what it takes to make sure it’s supported and preserved.”

East asked a similar question of Craig Russell, a coach and teacher at Winter Park High School and also a first-time candidate. (Stockton Reeves, a third candidate in the Seat 2 race, was not interviewed because East said he invited the candidates who reached out to him.)

“What I’ve already been doing at the high school is just that,” said Russell, who grew up in the city and lives south of AdventHealth Winter Park. “There’s a word out there … ‘charm.’ I don’t think it does the city justice. This city is rich with history and tradition and it needs to be honored and respected.”

Russell, who would be the first Black city commissioner in more than 100 years if elected on Tuesday, mentioned an African proverb that he said meant “we really need to know where we’ve come from to see where we’re going” and cited as an example that he wants all the students at the high school to learn the Alma Mater.

East also asked the candidates if they agreed with the voters’ decision in 2022 to approve a series of charter amendments that requires a supermajority (at least four votes rather than just three votes on the City Commission) to pass certain land use changes. Those changes include the sale of city property, rezoning parks and public land and rezoning residential land to a non-residential use and rezoning lakefront land from residential to commercial, mixed use or higher density residential.

Mayor Phil Anderson, who is not running for reelection and will leave office in April, championed the amendments. Others in the city campaigned against them because they saw them as potential blocks to new development.

Johnson said he voted for the amendments on the 2022 ballot and continues to support them today. He said the supermajority requirement is one of the best tools to help preserve Winter Park.

“My whole reason for running is preserving the charm of Winter Park,” he said. “I’d be hard pressed to think of a circumstance where I would support changing residential to commercial.”

Such land changes have happened on the west side in recent decades, which has reshaped the neighborhood.

Russell took a different position and said he does not think the residents got it right with the charter amendments when they passed them by wide margins.

“There’s two sides to that story,” he said. “You have the voters who voted on it, obviously, and then residents who didn’t necessarily understand it … It’s something I’d like to revisit and speak to the experts and see how historically it’s benefited the city and also talk to the residents, not just the voters. To me, there’s a large majority of the residents that didn’t get a chance to speak on it.”

Asked about the biggest challenge to the city, Russell said it’s the current divisiveness.

“We’re divided,” he said. “It’s like a high school. It’s very cliquey.”

Johnson has said the biggest issue is future development and shaping how Winter Park looks over the coming decades. Asked why he should be the next commissioner Johnson said he considers his experience with law and understanding the “sneaky” ways some developers do things would be an asset to the city.

“I don’t look like you,” said Johnson, who is white. “I don’t look like one of my opponents … I can tell you I will fight for the west side. My job will be to protect the city’s charm, including the charm that exists on the West side.”

East said what matters to him is whether candidates care about the issues that touch residents.

“I think on the west side, one of the things is do you care?” he said in the video. “It’s not a matter of what what you look like … or your background … or are you white or black? It’s do you really care about the west side? Do you really care about what happens to me and my family? And if the answer is you care, then you’re a good candidate for the job.”

Sheila DeCiccio

Sheila DeCiccio talks with residents at a meet-and-greet event. (Courtesy of DeCiccio’s campaign.)

Russell told East his experience at the school as well as with the nonprofit he started with his wife, Army of Angels, is what qualifies him for the job. He said he is passionate about serving families in crisis as well as his relationship with students.

“I feel I can continue to serve by speaking for them and not to them,” he said.

East also interviewed DeCiccio, the current vice mayor who is running for mayor. Her opponent, Michael Cameron, declined to appear.

If elected on Tuesday, DeCiccio would be the first woman to serve as mayor in Winter Park.

“We have witnessed firsthand your diligent care for residents, focus on
neighborhood charm and sincere concern for infrastructure, which align with our values,” read the alliance’s endorsement letter of DeCiccio.

She highlighted her experience tackling some of the city’s biggest infrastructure needs such as pushing a sense of urgency to fix flooding in west side neighborhoods and elsewhere. She said she supports the supermajority amendments and said residents “overwhelming” spoke in favor of them at the ballot box.

DeCiccio said she wants to address “divisiveness” that is “creeping in” to the city.

“I really want to work to bring everybody together,” she said.


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Commission delays final approval on leaf blower referendum

Commission delays final approval on leaf blower referendum

Commission delays final approval on leaf blower referendum

Issue still not settled as two commissioners asked for more information

March 13, 2024

By Beth Kassab

Winter Park commissioners on Wednesday punted the final approval for a voter referendum on gas leaf blowers until April when a new mayor will likely preside over the hearing.

The decision came after two votes ended in a 2-2 tie, meaning no action could be taken on the matter. Commissioner Todd Weaver was traveling and absent from the meeting.

Commissioners Sheila DeCiccio, who is running for mayor, and Marty Sullivan said they wanted to delay the vote on the referendum, which would ask voters next year if they want a ban on gas powered leaf blowers to stay in place.

Both DeCiccio and Sullivan raised questions about whether Gov. Ron DeSantis could veto language in the recently passed state budget that was inserted by Sen. Jason Brodeur to stop cities from banning gas leaf blowers.

The governor has about two weeks to veto line items once he receives the state budget, which hasn’t yet happened.

There’s no indication a veto is under consideration.

Winter Park commissioners adopted the ban in 2022 as a way to address resident complaints about the loud noise caused by the devices and cut down on harmful emissions and air pollutants. But the board opted to delay enacting the change to give residents and landscape companies time to transition to battery-powered blowers.

In recent months, as the June enactment date was approaching, landscape companies rallied for a repeal of the ordinance, citing burdensome costs of the battery models and other concerns like whether those models would be powerful enough to do the job.

Brodeur heard those complaints and decided to intervene at the state level.

But DeCiccio and Sullivan also questioned whether Brodeur’s preemption applies to Winter Park.

Brodeur told the Voice the language does apply to the city and he purposefully did that as an extra measure to keep the city from enacting the ban until the summer of 2025 at the earliest.

But the way the preemption is worded appears to only prohibit cities and counties from adopting new ordinances or amending current ordinances before the summer of 2025. Winter Park’s city attorney agreed with that interpretation.

If the city’s referendum does not go forward then the ordinance is set to take effect this summer, though the commission delayed issuing any fines for violations until January.

Mayor Phil Anderson and Commissioner Kris Cruzada said they wanted to finalize the referendum and let the voters have a say on the matter. But they lost in a 2-2 tie.

The matter is now set to be debated again at the April 10 City Commission meeting.

Anderson is expected to preside over his final meeting on March 27 and hand over the gavel to a new mayor during the April 10 meeting. Depending on the outcome of next week’s election, a new commissioner for Seat 2 could also be sworn in during that meeting.

But the Seat 2 race is a three-way contest and it’s possible it will head into a run-off that won’t be decided until April 16. If that happens, then there will only be four commissioners to decide the issue on April 10. 


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Republicans lead early voting in Winter Park and across Orange

Republicans lead early voting in Winter Park and across Orange

Republicans lead early voting in Winter Park and across Orange

How will the GOP’s presidential primary impact municipal elections?

March 13, 2024

By Beth Kassab

Republicans are turning out by a big margin in Orange County ahead of next week’s GOP presidential primary, which is also regular spring elections for Winter Park and other local cities such as Eatonville and Maitland.

Of all the county’s early voting sites, the Winter Park Library has seen the highest number of votes cast so far with 1,339, according to the Orange County Supervisor of Elections. Of those, nearly 60% or 774 are from registered Republicans. About 30%, or 395, are from Democrats. Another 160 votes are from people registered without a party affiliation.

Anyone can vote at the early voting sites, which means some of the votes cast at the library could have been from voters who live outside Winter Park. But it’s the best early indicator of how voting stands so far.

In Winter Park there are about 22,000 active registered voters. They are close to evenly split among Republicans and Democrats with Republicans leading slightly with 8,300 versus 7,700 Democrats.

Yet Republicans are driving early voting by nearly 2 to 1.

County wide, Republicans are driving early votes by an even wider margin with more than 23,000 ballots so far compared to 4,000 from Democrats.

Winter Park’s election for mayor and Seat 2 commissioner are technically non-partisan, but party politics often plays a role.

The Republican women’s club in Winter Park, for example, held an event for Seat 2 candidate Stockton Reeves, who has also run as a Republican (and lost) for a Florida House seat.

Past elections, though, have shown Winter Parkers to be discerning when it comes to local politics. Issues like development rules, brick streets, lake quality and parks rarely appear to fall along strict party lines.

In other words, it’s not clear that Donald Trump’s name on the ballot will drive turnout for a single candidate among Republican voters in the municipal races. Democrats decided last year to scrap their presidential primary in Florida in an effort to aid President Joe Biden.

Jason Johnson and Craig Russell, who are also running for Seat 2, appear to have refrained from party rhetoric in their campaigns.

The key differences between Johnson and Russell come in the form of their responses on development questions. For instance, Russell, who is backed by the Winter Park Chamber of Commerce has said he is open to revisiting the original Orange Avenue Overlay, which allows for taller buildings and more dense development, and is also open to lessening the requirements for developers to build parking spaces. Johnson has said he would not return to the old zoning rules and does not want to see major changes in the parking code.

Early precinct data from the nine precincts with Winter Park addresses shows 2,685 returned mail ballots and early votes so far, according to the supervisor’s office. A party breakdown for that data isn’t available.

The most votes so far are associated with the precinct at the Winter Park YMCA, which has 538 returned mail votes and 159 early votes. That’s followed by the Winter Park 9th Grade Center, which totals 255 returned mail votes and 107 early votes and Orange Technical College with 212 returned mail votes and 98 early votes.

Early voting runs through Sunday from 10 a.m. to 6 p.m. each day. Click here for locations.  

Polls open on Election Day (March 19) at 7 a.m. and close at 7 p.m. Voters can find their precincts here.


Donald Trump may be the clear Republican nominee for president, but the question

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Candidates’ final push for votes underway

Candidates’ final push for votes underway

Candidates' final push for votes underway

With just one week until Election Day, voters hear closing arguments from candidates

March 11, 2024

By Beth Kassab

With just seven days until election day, candidates are making a final push for votes this week and the latest financial reports reveal who leads in campaign spending and fundraising.

Jason Johnson and Craig Russell, both running for Seat 2 on the City Commission, released dueling closing argument emails over the weekend.

“The results of this race could come down to just a handful of votes,” read an email to voters from Russell’s campaign manager.

The coach and teacher at Winter Park High School is running “to promote transparency, accountability and representation for all our residents,” the email stated.

Russell is bringing the biggest money to the race with his campaign spending $42,000 so far — more than the other two candidates in his race as well the two candidates in the mayor’s race.

The difference is even more stark when coupled with the money raised by the Winter Park Chamber of Commerce’s political action committee known as Winter PAC, which raised $21,000 and spent more than $10,000 on Russell’s behalf, according to the reports filed with the city clerk. Russell is the only candidate endorsed by the chamber.

Contributions to the PAC include $7,500 from developer Allan Keen and his wife and one of his business entities, Development Opportunities Holding. Another $1,000 is from Automotive Services Network, a company controlled by the Holler family, which has also been a big contributor to Russell’s campaign account.

The Hollers, which own car dealerships as well as high-visibility Winter Park real estate along Fairbanks, Orange and Park avenues, contributed $8,000 to Russell from their associated businesses. Another $3,000 came from Holler family attorney Frank Hamner and his businesses.

Hamner told the Voice recently that the contributions from himself and the Holler family are unrelated to the family’s development interests in the city and that they know and support Russell as a community and nonprofit leader who serves underprivileged families.

The City Commission balked in January at a request from city staff to include some changes in the comprehensive plan that could potentially make it easier for the Hollers to develop a lot along the busy intersection of Fairbanks Avenue and Denning Drive, where the city is also trying to obtain more land for turn lanes to ease traffic congestion.

At a candidate forum last week at Westminster Winter Park, a senior living community, Russell appeared to indirectly address the money supporting his campaign.

“I’m nobody’s puppet as some of my opponents might believe,” he said, according to a video posted on YouTube of the event. “I speak for the residents and myself and that alone,” noting that he believed in mindful growth “not like Maitland,” in response to a question from the moderator about how Winter Park should balance neighborhood stability with business growth.

Russell also called out what he sees as “an elitist mindset” among current leaders that he says is “creating stagnation in this city that will inhibit its ability to grow.”

Johnson, who has raised $43,000 and spent $32,000, responded by saying the question sounded like “it was drafted by somebody at the Winter Park Chamber of Commerce, whose sole goal is to advance the interests of developers.”

“My job here is to preserve our residential communities,” he said. “We don’t need to pave over this city for commercial development.”

In Johnson’s email to voters over the weekend he attempted to further draw a distinction from his opponent, noting that he was not endorsed by the Chamber.

“I personally consider this a badge of honor,” he wrote. “I oppose the excessive high-rise and high-density developments that the Chamber supports. I support attractive and in-scale development that enhances the charm of Winter Park.”

Stockton Reeves, who has raised $69,000 and spent $42,000, emphasized his long family history in Winter Park and said he believes there is already enough affordable and workforce housing in the city. Most of his campaign funds have come in the form of a loan — worth $53,000 — from himself.

If one of the three candidates does not capture more than 50% of the vote on March 19, then the top two vote getters will head into a runoff to be decided on April 16.

In the mayor’s race, Sheila DeCiccio, the current vice mayor, has raised more than $40,000 and spent $30,000 so far. In recent days she has sent out an email thanking supporters and inviting them to an election night party.

DeCiccio also appeared at a forum at Westminster and, as has become a pattern in her race, she was the only candidate to show up.

Michael Cameron, her opponent, has not appeared at any of the public forums or at either private forum held for seniors at the Westminster and Mayflower communities.

He has raised $5,700 and spent nearly all of that on a political consulting firm.

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